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In episode 11 of EnterpriseReady, Grant speaks with Bob Tinker, founder and former CEO of MobileIron. They discuss the frameworks that Bob has developed for building a go-to-market playbook, as well as the importance of customer urgency in the enterprise space.

Bob Tinker is the Co-Founder and former CEO of MobileIron. He co-authored Survival to Thrival, an acclaimed book that aims to guide enterprise entrepreneurs through all stages of company growth.


Grant Miller: All right, Bob. Thank you so much for joining us.

Bob Tinker: Grant, thanks for having me.

Grant: Cool. Let's dive right in. Tell us a little bit about your background.

Bob: I'm a three time entrepreneur, originally an engineer, and my first job out of college was an IT guy at a bank.

I used to be on the customer side, and accidentally ended up in sales when I was doing customer support for some large accounts and the account rep left the bank.

I ended up running sales for some large accounts and I realized that there was a two-class system in business, where there were the business people and the technology people.

It's a little bit less so now, but definitely the case in the 90s in banking, and frankly that was frustrating because I liked technology and I liked business.

I moved out to the Bay Area to go to business school and that was the thesis to try and be able to participate in both sides. But then I realized it really wasn't going to change things.

My big aha was here in Silicon Valley, the technology is the business.

That was the beginning of my entrepreneurial career. Fast forward, three different startups. First one, voice over IP company. Frankly, that one failed. It was too early.

Grant: Was that a consumer company, or is that in the enterprise space?

Bob: No, that was an enterprise voice over IP in 1998.

Grant: Cool.

Bob: Yeah, it was just one of those things where it's too early. In 2002--

Grant: Too early from the technology perspective, or--?

Bob: Technology, market, and urgency. Think about 1998, 2000. V oice over IP was cool, but why would anybody change?

There wasn't a compelling event for somebody to rip out their existing voice infrastructure and put in voice over IP.

It was one of those things that happened slowly over the course of a 20-year period. But that's a rough place to be a startup.

Grant: Yeah. The 20-year start-up is--

Bob: A 20-year sales cycle? It's a rough world. My second company was an enterprise Wi-Fi company called Airspace, and I was the first business guy there.

I wasn't one of the founders, but I was the first business guy there. That was a great experience. I went from zero to $80 million over four years.

Grant: What did you guys do? You say, "Enterprise Wi-Fi?"

Bob: Enterprise Wi-Fi. If you remember back in 2002, this Centrino chipset first showed up in laptops and all of a sudden people started trying to use Wi-Fi at work.

The first answer was, "Let me go to Fry's and get some consumer access points and sprinkle them around the office."

Then all of a sudden, large companies were like, "We need to figure out how to have Wi-Fi for everyone." So, we sold enterprise Wi-Fi infrastructure.

Cisco bought us for $450 million in 2005 and we became the Cisco Wireless Business Unit.

Grant: You would go into large enterprises and physically install the routers and the access points and all that hardware?

Bob: Yeah. The big innovation was, "How do you move from standalone access points to thinking about Wi-Fi as a system?"

We had enterprise Wi-Fi access points, but they were all centrally controlled by basically a wireless controller. We adopted a cellular architecture model for enterprise Wi-Fi.

Grant: Cool.

Bob: That turned out to be both good timing in terms of market urgency, because now Wi-Fi was in laptops and customers needed to do something about it, and we had a solution to do that.

We grew from zero to $80 million over four years, and that was a great growth experience for us.

Grant: It relates to what you end up doing next, right?

Bob: Right. Another transition, tidal-wave urgency that is forced by a macro shift in the market.

The way you can picture it is like every once in a while in a market, there's a tidal wave-- Or, it doesn't even have to be a tidal wave, just a wave. If you can build a good surfboard and surf on that wave, you can often build a pretty good business.

For Airspace, the wave was Wi-Fi showing up at work, the Wi-Fi ready devices, and then people needed Wi-Fi infrastructure to attach it to.

Grant: Because before that everything was landline and hard wired and you sat at a desk and you plugged in, and that's how you got the internet.

Bob: Now all of a sudden laptops had Wi-Fi and people wanted to work wherever they were.

Grant: People were probably just plugging a router on top of their endpoint.

Bob: Which was a huge security issue actually, because people were just plugging in consumer access points under their desk.

Grant: Using their one connection to make it a Wi-Fi so they could walk around.

Bob: Yeah, they were very popular. Except for with the security team.

Grant: Exactly.

Bob: But that's a great point, that it was a transition or a wave in the market, that if you build a good product to surf on that you can build a good business.

Grant: Interestingly, also driven by the changing employee needs. They were bringing in technology that they wanted to use and made their lives better, because they didn't have to plug in and every meeting and they could walk around and show people stuff. That makes a lot of sense.

Bob: End user-driven demand. Exactly. You can think about anytime a new type of client, or application, or end-user use case shows up at work.

Often the back end infrastructure has to figure out how to respond.

Grant: Yeah, it's a great point.

Bob: My last company in 2008 was a mobile security company called MobileIron, I was the co-founder and CEO of that.

We built that from three people on a white board in 2008 to when I stepped aside in 2016, we were $160 million dollars a year in revenue, 12,000 enterprise customers, public on Nasdaq and 1,000 employees.

Grant: Yeah, it's a pretty big company.

Bob: Yeah. They're really proud of that. We built an industry, created a new category, and built a standalone business that's still thriving.

Grant: That's great. So now you're spending your time helping people understand the challenges around building enterprise software companies.

Bob: Yes. What I've been doing over the last year is a combination of seed investing and writing books on B2B entrepreneurship, and I'm working on a new project now where me and another colleague are actually going to be buying small SaaS companies.

Grant: Cool. You wrote a book called Survival to Thrival, which I've read most of, but I have seen you talk and I've watched a bunch of other things so I'm really excited to dive into some of these topics you bring up there.

Bob: I'd love to.

Grant: For anyone listening, there's-- Just go get the book, it's amazing. It has a bunch of frameworks and ways to visualize the stuff we'll talk about, so let's dive in. Where should we start here?

Bob: Looking back through my experience at Airspace and MobileIron, one of the things that I found frustrating was that--

We spend so much time trying to build a product that customers want that often we don't think through, "What's the missing link between winning your first 10 customers and winning your next 1,000 customers?"

Bob: It's that building of a go-to market that as a first time CEO, a product oriented CEO, frankly I struggled with and had to learn along the way. I don't think I'm alone in that a lot of entrepreneurs and first time CEOs, particularly product-centric CEOs, figuring out how to build a repeatable go-to market to unlock growth is not necessarily intuitive.

Grant: Yeah, it's quite hard. From my perspective you have an idea when you're starting and you know what you want to build the first time, and you start to show it to people and then you start to get feedback.

Bob: Right. You're iterating, and iterating on the product. We generally have a pretty good handle on what product market fit is.

Grant: Sure.

Bob: How do you get your first 10, 15, 20 paying, reference customers that say good things about your product? That iterative process feels somewhat natural to a product-centric CEO.

For me at MobileIron in 2008, we spent the first six months talking to customers before we wrote a line of code or raised a dollar of venture capital.

We weren't sure what the technology would be, but we wanted to make sure we really understood what the problem was that the customers were going to go solve.

Then we backed into, "OK. What's the technology solution we need to be able to go solve that?"

Grant: Let's dig in there a little bit. Did you have a space in mind? Did you have an initial product thesis?

Bob: Yes. Remember we talked about the wave phenomena?

Grant: Yeah, right. 2008.

Bob: It was the very beginning of smartphones. iPhone had just been launched, but it was consumer-oriented. It was a BlackBerry, Symbian, Windows Phone world. I laugh about that now.

But you could start to see people bring them into work and be like, "Man, I want this." You could just feel it. You could see it in people's eyes. Even though it was messy and clunky and didn't always work very well, people were like, "Yeah, I want this."

As a side effect of one of my jobs at Cisco, I got to work with the Cisco IT team in 2007 when we rolled out 25,000 Palm Trios. It was a mess. It was really hard on IT. They were bleeding from the eyeballs.

Grant: How many again?

Bob: 25,000 Palm Trios. It was probably the largest smartphone deployment of the world at the time.

Grant: That's amazing.

Bob: IT was dying, but users were still like, "Gimme-gimme-gimme." I was like, "OK, there's something there. Somebody should solve that problem."

When Ajay and Suresh, who were my co-founders, showed me what they were thinking about, "Let's go see if we can figure out how to help smartphones get used at work."

That was as specific as we got in terms of the space, then that's where spending time talking to customers for six months to really understand what the problems were, what their challenges would be.

Roll the clock forward 12, 18 months and try and do a little future prediction, because it takes you a while to build a company and you want to build for what the market's going to need in the future, not necessarily what they need right now.

Grant: OK. How did you get in the door with these folks to even have those conversations? Are these folks you met from--?

Bob: That's a great question. One of the things I learned and that we learned with that early customer research is that a lot of potential customers are willing to be helpful.

If you just say, "Look. We're thinking about building a company, we've got this idea about a general space. We'd love some feedback, we'd love some advice."

People love to give feedback and love to give advice. We probably had 70 or 80 customer meetings getting feedback and advice.

Some of it was just finding people through our network and calling them, our seed investor was helpful in introducing us to customers.

Customers from our previous companies, we'd ask them who the person was who was working on it.

But if you just ask people, "Look. We're working on idea, we'd love some advice, we'd love some input." You'd be surprised, a lot of people are willing to help.

Interestingly, those 80 customer meetings eventually turned into something we called "Teaching customers."

There's about 40 of them where you meet with a potential customer and you get advice where you're like, "They seem to understand the problem. Intuitively, they seem to get it."

You start to collect them and they become these customers that give you feedback, not just once, but multiple times.

They become what we call "Teaching customers." And then over time, if you picture a funnel, there's 40 teaching customers-- Some of them fell off the list, but then 15 of them became our alpha customers and then seven of them became our betas, and then five became our paying reference customers.

So in many ways, in addition to really figuring out what we were going to go build, a lot of them ended up becoming the pipeline for future alphas and betas.

Grant: Sure. The interesting part there is just even how you got to them. It feels like your relationships from Airspace were valuable.

Bob: Previous companies, sometimes just going to conferences and walking around talking to people and cold calling.

Grant: OK. It was a lot of--? You did some cold calling?

Bob: Yeah.

Grant: OK, great. But you had some credibility, so be would at least think "OK, these guys have-- They know a little bit about enterprise software and doing IT stuff."

Bob: Probably on the margin, yeah. But other than our previous customers I'm not sure the other people knew who we were.

Grant: OK.

Bob: At some level it was a karmic deposit to the universe that they were just willing to take a phone call, be willing to help.

Grant: Yeah, I love that. Would you go meet them in person and do a phone call, remote, what was the--?

Bob: It was a mix of them. I'd bet it was probably 50% phone call, 50% face to face. But over time what happened was, you start to feel the customers and prospects are willing to keep giving you feedback and advice over time.

Grant: Your initial thesis was around mobile and that there was-- You could help secure these devices?

Bob: It was just that-- Actually, it was more general than that. It was like, "These things are coming into the office and people are going to use them at work. How can we help?"

Like, "What are the problems that the enterprise and IT is going to have as that happens?" Part of it was a security problem, part of was a management problem, part of it was we started to hear about new things.

This idea that people wanted to bring their personal smartphones to work. Remember, BYOD had not been really invented at this time.

Grant: So this is--? OK.

Bob: This is pre-BYOD. If you were really important you got a BlackBerry at work. BlackBerry was a pager that just turned into a phone in 2008. You've got to rewind the time machine here.

Grant: So you were thinking, "How do we not--?"

Bob: Palm Trio, BlackBerry, Symbian days.

Grant: But from IT out, how do we distribute phones?

Bob: Everything. "What were the problems that enterprises were going to have as these things start to show up more?"

Grant: But initially your thought was that the IT teams would distribute them.

Bob: Yeah, because that's the way it was always done before.

Grant: Right.

Bob: Then we start to hear about things about how people had this personal phone, and "Why can't I use this at work?"

"Because that's not allowed." Or, "You've got to keep your data separate." Or, "We hadn't really thought about that before."

Grant: OK. Because ultimately that's what MobileIron really became, right?

Bob: Multi-OS and BYOD. It was really, "How do you say 'Yes' to mobile and secure and manage it."

Grant: Because very few companies actually give out-- They don't give you a company-issued phone anymore.

Bob: No, but you rewind from 2008 to 2012, probably 75% of the devices inside companies were company-issued. You look at that now and it's laughable, but that was the way it was.

Interestingly that pattern of, "People are trying to bring their phones to work. Wait, that means there's going to be a mixture of personal data and work data on there. That's going to be another problem that's going to need to be solved."

As you start to spend time with customers and figure out what these challenges are going to be, you can start to reverse into "What's the product you want to build? What problems do you want to solve?"

A great example of that is that we invented a concept called "Selective Wipe." Which is like, "If you have a BYOD device and you want to pull out your work content because you leave the company but leave your pictures and music alone--"

Everybody takes it for granted now that that's the way it works, but that was not the case in 2010. We invented that concept which is now just part of the way it's done.

Grant: That's cool. So that--?

Bob: Came from customer meetings and understanding what these challenges were and figuring out a problem solve.

Grant: OK, then when did it become really apparent that was the problem that you needed to solve? Or were there--?

Bob: In the early days as you're starting to do your customer research and figure out your problems, then you're like, "We're going to go build a product."

You start iterating on "It's going to do this." Customer gives you feedback, "Let's add that and see if they're interested. They're interested," or, "They're not interested."

You start getting this iteration and feedback about what people are interested and not interested in, and why they want to keep talking to you or why they don't want to keep talking to you.

You're getting all these data points. What's confusing at the time is that you have this bull's eye that you think you know. You're like, "OK, I think I 75% know."

What we ended up finding is that we needed to cast a slightly wider net from what we thought our bull's eye was, from talking to customers, and explore things a little bit to the left, or a little bit to the right, or a little bit up or a little bit down. Because you're really looking for hotspots where you start to see multiple customers with the same problem, looking for the same solution.

The confusing part is we actually saw like two or three different clusters of where we were seeing customer interest from, and if you imagine a bull's eye with a slightly wider net around it, you get these three hotspots.

It was fortunate that we had three hot spots, because sometimes you get zero.

Grant: Sure.

Bob: I'll tell you what it felt like, which is in some ways exploring these adjacencies at the time felt like heresy. It felt like we were betraying our founding idea. They were like, "This is what we're going to go build and this is what we're going to do based on customer feedback."

Grant: You rally the team around this, and then--

Bob: Then it's like, "Wait a minute. We're going to test this thing over here." "Wait a minute, that's not exactly what we said we were going to do." It feels like heresy.

This one, I'll give you a very specific example, at this time the mobile world was all BlackBerry, Symbian and Windows Phone.

Grant: Isn't it still?

Bob: Somewhere in the world. Maybe in Ottawa, Canada. The iPhone had just come out, and at that point it was just a consumer device and nobody was using it at work.

But we started to see some customers, "We'd love to try and figure out how to use iPhone at work."

But if you looked at market data, it was "It's all Symbian, BlackBerry, Windows Phone. iPhone is really not in enterprise, so don't pay any attention that."

If we'd actually been analytical about it we would've ignored it. But we started hearing customer feedback that they were struggling with it. They're like, "Dude, can you help me with iPhone?"

Grant: Is this right after the iPhone launch, like instantly?

Bob: It was like, 12 months.

Grant: OK, so maybe the iPhone 3G comes out and it starts to really--

Bob: It was way before that.

Grant: It was before that? OK, great.

Bob: Yeah. We started doing some experiments, we actually built our first prototype for our iPhone management security product on a couple of Post-It notes.

I still have it somewhere, actually. It was a controversy at the time about, "Should we spend energy and resources to go prototype this thing and go test this adjacency?"

Grant: How big was the company? How many people at this point?

Bob: 20.

Grant: OK. 20 people. A pretty good size of people that you're moving around, saying "We got this really interesting thing over here we might want to go test."

Bob: Yeah. Because we were seeing traction in some of the other parts of the market, so we were like "Let's go test this adjacency." It feels like a distraction. You can start to translate "Adjacency" into "Distraction."

Grant: Yeah, you got to focus, right? You got to focus.

Bob: Focus, focus, focus. But the reality is if you focus, focus, focus and pick the wrong thing, you're dead.

Grant: Great point.

Bob: More often than not the hot spot that actually helps you unlock growth is a little bit to the left, a little bit to the right, or a little bit up and a little bit down.

You have to cast a slightly wider net and it's hard at the time, because you've got limited resources, limited time. You've got limited focus and it frankly feels like heresy because you feel like you're betraying your founding idea a little bit.

But I think if you talk to most founders that have built successful companies and really pull apart the origin story, the success was unlocked by something that wasn't quite exactly what they thought it was going to be in the beginning.

That's normal and that's good, but you have to give yourself just enough rope to find it.

Grant: For you that was just, "We have all these iPhones. Help me with this iPhone problem." So you started building features around that?

Bob: Yeah. "How do you solve the problem for managing, securing and deploying iPhones in the enterprise?" Apple hadn't figured it out at the time.

Grant: Was this also from a central IT out, not from BYOD at that point?

Bob: Central IT out, yeah. It wasn't even BYOD at this point.

Grant: Like, "We're a cool company. We want to give our employees iPhones instead of Blackberries. How do we do that? Because the CEO wants an iPhone. They don't want to have a BlackBerry anymore."

Bob: That's a great example of finding urgency-- One of our early deals was with a large biotech company and they had no business buying a mobile management security product from a little company of 30 people.

Why would they buy from us? But the problem was, their exact team was beating the snot out of the IT team and basically said, "Figure out how to let us use iPhones or you're fired."

The IT team was like, "OK. We'll go figure that out.".

Grant: That's urgency.

Bob: That urgency is what gave permission to these buyers to make a bet on a small little company with very few customers that might die someday.

You have to put yourself in the position of your customers in their early days, like our very first customer was a company called Windsor Foods. If you turn over a Costco burrito it's made by Windsor Foods.

Grant: OK.

Bob: Stephan was director of IT at Windsor Foods and our first deal was like $6,000 dollars. But imagine the conversation Stephan had with his boss.

"I got to go by this management security product at this company called MobileIron for mobility." The boss says, "Great. Tell me about them."

"They're 25 people." "Great. Who are the customers they've had?" "We're the first." "Are they even going to be around?" "I don't know." Put yourself in the shoes of Stephan, he had to really stick out his neck.

Grant: Being first is tough.

Bob: Even like the first five, six, seven, eight, they're all making the same bet.

Grant: But you did give him risk-adjusted pricing. Because $6,000--

Bob: At that point it was really just about, "Just pay us something."

Grant: That's a good deal.

Bob: It was a great deal. You just want customers using it and being able to say good things. Product-market fit is, "How do you get those first 10, 15, 20 customers that are willing to use your product, say good things and pay you some money?"

That's really the test. But one of the hard things at that point in time, and I think a lot of early stage companies go through this, you remember the multiple hotspots I talked about.

We felt these couple of clusters that eventually you have to pick one. We probably had 15, 20 customers and they were spread across or the iPhone hotspot cluster.

We had some people doing Symbian and BlackBerry, and we actually had this other application to help people manage costs on mobile devices. That was a big issue at the time.

Grant: OK. Like manage the minutes or data, or something?

Bob: International roaming and surprise roaming, plan overages. It was a huge deal in 2008, 2009.

Listening to customers, you're trying to solve their problems and we heard a lot of customers articulating that problem. We won some customers for that part of the product.

If you imagine us having these three clusters of customers that had three different types of characteristics, we eventually had to pick one to go focus on. As a result, we had to prune and stop doing that product that those other customers bought.

That was brutal. Here's this company, PPDI, big company in North Carolina that basically bought this product from us.

They made a bet, they did the Stephan thing where they went to the boss and said, "I'm going to buy this product from this company you've never heard of that's going to help us."

Grant: You shook their hand--?

Bob: Shook their hand, took their money--

Grant: Great.

Bob: Gave them the product, and then we had to call them back like three or four months later and be like, "We're end-of-lifing that product." That was brutal, but you have to.

You have to prune these things and once you find your hotspot, focus on that. Build your go-to market on that, build your repeatability on that.

These other things, it'll hold you back and it'll get in the way. You're screwing some customers as a result and that's painful.

You want to be customer-centric and these people bet on you, and your stranding them. I flew to North Carolina, I wanted to go meet the customer.

I'm like, "All right, look. I'm really sorry to tell you we're going to be end-of-lifing this."

Grant: You flew there then?

Bob: I flew there and I actually walked in with a check and gave them their money back. Which was a lot of money at the time for us, like we de-booked it.

I told him why, I said, "Look. This is a valid problem, but we're going to be focused on another problem. Frankly, we could maybe ham-and-egg it and try and keep the product alive that you bought from us, but we're just not going to do a very good job of it. You're going to end up regretting it and we're going to have regretting it, so we might as well just like not do it."

We gave them their money back. Now, the interesting epilogue to that story is two years later they became a customer on our main line product.

Grant: OK, nice.

Bob: So eventually the hotspot that other customers we had seen, PPDI had as well. That was a nice epilogue to that story.

Grant: You didn't burn the bridge so much that they weren't willing to work with you in the future, so I'm guessing flying there and handing them the check--

Those are all, that's a lot. The hardest part is the human part. They trusted you to do this thing, so you're going back--

Bob: Internally your sales team is like, "Wait a minute. We're not going to sell this anymore? We got customers we could sell this to." You're an early stage CEO going, "I'm just trying to win some customers and get some revenue."

Grant: Got to get that ARR up.

Bob: I'm saying no to that, and it's super counterintuitive and really painful at the time.

But getting to "How do you really unlock growth?" You've got to find that hot spot that has urgency.

I often get asked, "How do you create urgency?" In my head the little voice says, "If you're asking that question, you're already half in trouble."

Grant: Sure.

Bob: Because it's much better to find urgency that's already there. If you're in a situation where you have to create urgency, it's doable, you can do it. It's not a fool's errand but it's way better if you can actually just find urgency and capitalize on it.

Grant: Yeah, it's hard to create urgency. I've had two companies, Replicated included, where urgency is always a problem.

"How do we get these folks to really get how much this is going to help them now?" So you end up trying to do things and calculate ROI and show them better, trying to create metrics around it.

But ultimately, if they don't have the urgency to do it right now it's hard to get them to jump.

Bob: "Why buy now versus six months from now?" Doing nothing is often your biggest competitor. Being able to find urgency--

Grant: Like, "You're going to get fired if you can't give me an iPhone." Right?

Bob: Right. We found urgency.

Grant: That's urgency, that's huge urgency.

Bob: That was a big deal. Often you see these big waves that are creating transitions in markets. For us, it was the transition to mobility. "What do I do at iPhone? What do I do at BYOD? What do I do about apps?"/span>

There were these waves of change that created urgency inside customers. I think that happens all around enterprise software.

There's waves of change that force or create problems where people go, "Crap. I've got to do something."

If you can find one of those hotspots that has urgency, that's one of the key ingredients to really being able to unlock growth.

Because you can have a great product, you can have a great go-to-market playbook, but if there's no urgency you're just not going to see growth, it's going to be a slog.

Grant: You have these frameworks for company building and enterprise software creation--

Bob: Benefit of hindsight.

Grant: Right. You approached everything you did at MobileIron with how you knew all this ahead of time.

Bob: Yeah. The amount of battle scars on my back is numerous.

Grant: These are hard won frameworks that you have created.

Bob: Stuff I wish I'd known.

Grant: Right.

Bob: This is the, "If I could write myself a letter sitting on my desk ten years ago, what would I tell myself?" This would be one of them.

Grant: But that urgency, first, you have idea creation and you have product-market fit. Where do you put urgency in that?

Bob: Let me give you the context on this. The real struggles in enterprise software and building B2B SaaS companies is a lot of times you can get to product-market fit.

You can really ham and egg your way to your first 10, 15, 20 customers and then you're like, "OK great. I've got product market fit, time to grow. Let's go hire a bunch of salespeople and invest in marketing."

And you wake up six months later and you went from 20 customers to like 22 or 24 or 25, and your burn rate went up and everybody's looking around going, "Scary."

There's a ton of companies that get the product market fit but never unlock growth. The reason is that there's, I think in my mind, a missing link between those two.

That when you look at all the B2B software companies that really unlock growth, they found something in between product-market fit and growth and the funny thing is it didn't really have a name.

Which is in and of itself interesting. So we coined the term "Go-to-market fit."

Grant: Which I think is perfect.

Bob: Which happened on the tail end of product market fit, which is "How do you find and win customers over and over and over again with some level of urgency?"

It sounds simple, but it's hard to do. This concept of go-to market fit I found really helpful. If you look through the rear-view mirror at MobileIron, we nailed go-to market fit.

What was that? It was number one, they found urgency, which answers the question of "Why now and not six months from now?" For us it was "The dude helped me with iPhone." It was, "Help me not get fired."

Grant: Right. "My CEO wants an iPhone."

Bob: Yeah, it's funny. I think if I was listening to this now, I would be laughing. Of course that's obvious now, but in 2009 that was not that obvious.

The second thing is, what's your go-to market model? How do you sell to higher sales people? Do you go up the middle? Do you do online evals and have inside sales, or are you a zero-touch sales model like a Twilio or SendGrid?

Like, "What is your sales model?" I think you've got to pick one, and then the third one is having a repeatable go-to market playbook, which is "How do you just find and win customers over and over again, from the first time you touch them to when you win them and make them successful?"

When you have those three things, you've got urgency, you've got your go-to-market model picked, and you've got a playbook you can do over and over and over again.

That's when companies unlock growth Just being able to have a framework around it that gives people a way to think about crossing and solving this missing link between product-market fit and growth is helpful.

It would maybe be useful to touch on this "How do you even figure out what your go-to-market looks like??

Grant: Yes. Let's dive into it. You have these great frameworks for each of these, right? Because most people think about "How do I want to sell this thing," and they don't really know how to think about it, and I think you have a really great way.

Bob: When I was going through this in 2009, I found this whole discussion super confusing.

I was like, "Big ticket, small ticket, complicated products, simple products, sell through the channel, not through the sales channel."

Grant: Right. "Is it over? What's your ACV? Is it over $50K?

Bob: I was like-- It was super confusing. The way I think about it now is through the benefit of hindsight.

If you think about a slider, on the left side you have heavy-touch sales, which is classic up the middle enterprise selling where you've got sales teams talking to customers.

In the middle of the slider you get what I call a "Marketing-led sales model," which is like you do digital demand generation, you drive customers to your website, may get them to an online eval.

You gather some metrics and then inside sales picks up the phone, starts calling and then closes. But a human picks up the ball about halfway through.

Then on the far right you've got product-led zero-touch sales, like what a Twilio or SendGrid does, where there's no sales people. It's almost self-service. "How do you figure out where on that spectrum you should be?"

Grant: Yeah, I think this is the question. Everyone understands that those are different models. But like, how do you know which one you are?

Bob: The first thing is I've seen a lot of companies get bum steers from their investors on this, because they'll be like "Go do frictionless zero-touch sales," because that's in vogue or in style right now.

Venture capitalists love it because you don't have to spend money on sales. So it is very efficient, great. The trick is there is no one right sales and go-to-market model.

There's only, "What's the right one for you and your product and your customers?" You have to pick whatever the right one is for you.

It's OK to experiment with different ones and have a thesis about what it is, but in order for you to unlock growth you really have to pick one.

Because I don't think small companies can run multiple go-to markets at the same time to unlock growth, you really get to pick one.

So, "How do you figure out where on the spectrum you live?" It was a couple of things that helped me.

One was there's a great article, Mark Leslie who is the CEO at Veritas now a professor at Stanford wrote, called Leslie's Compass. It's up on LinkedIn, you can look at it.

It's a good article about how to think about this. I actually found, interestingly, what simplified it for me is it all comes down to one question.

Grant: What's that question?

Bob: "How does the customer decide to buy?" It's not, "How do they physically buy?" Not the logistics of buying, not the characteristics of buying.

It's actually, "What is the cognitive process going on inside that customer for them to go from "I'm not buying" to "I'm buying."

Let me explain this for a sec, because think about the times where you've been a customer buying a product from a vendor. You went through a cognitive process from the first time you figured out your need to what you're going to pick.

Every purchasing decision goes through that same thing, so as you're winning your early deals and losing early deals, you tend to pay attention to why you lost and why you won.

At the same time, pay attention to how your customer actually made the decision to buy. Because if you think about that spectrum I talked about earlier, if the buyer and decider are the same person you can reach them over digital marketing and your products relatively well understood, you can do zero-touch sales.

You should be able to try that. But if the buyer and decider are two different people, like the VP of marketing and the CEO.

For example, look at Marketo or something like that. How did MobileIron decide to buy Marketo when we bought Marketo? My VP of marketing said, "I want to buy this.' Came to me, the CEO, and said, "Will you approve it?"

We talked about it for a little while and I said, "Yes." The buyer and decider were two different people, but they're right next to each other.

That one is in the middle of the spectrum, you've got two people, buyer and decider right next to each other. You can do marketing-led sales.

If the buying decision is more of a committee, where the cognitive process of making a decision to buy involves like five or six different people, you're probably going to need heavy-touch sales because part of sales' job is actually coordinating that decision inside the company.

What really simplified this problem for me is like, "How does your customer decide to buy? What's the cognitive process?" One person, buyer and decider, two people sitting right next to each other or there's a group of people.

For us at MobileIron, when we were selling large enterprise, it was the committee decision. There's like five or six different people involved so we couldn't do zero-touch sales if our life depended on it.

Grant: Yes. That was going to be my next question, do you think that there are any levers that a company can pull to move in one direction more than the other? Obviously, probably price. If you make it really expensive--

Bob: It's interesting. If people say, "It's a big ticket." Like, "Of course." The reason why high prices tend to lead to committee sales is the way companies buy. It's a big purchase process. More people are involved and if it's smaller less people are involved.

Price is more of a symptom of the decision, like if you have a product that is low-priced but has a committee decision, it's probably going to be a really tough sales model.

Grant: It's interesting to think about this.

Bob: You can have high price products that are relatively easy decisions. If you find those like, that's great.

Grant: Sure. But do you think that--? Are there other levers around, "OK. Is it cross-functional?"

What starts to make the buyer and decider a different person, is it company size or what are some of the other levers if you want to try to move it?

In terms of, "We want to start to go more enterprise, we want to start to go more self-serve." Are there any things you would--?

Bob: A lot of it has to do with the type of product and the problem you're solving.

Grant: OK, right.

Bob: If you look at the low friction sales models, they tend to be like you're selling to an engineer in dev ops, or you're selling to the marketing manager and they can just decide to do it.

If you're solving a relatively narrow problem that has a small audience, that tends to lean to a relatively well-understood product.

If your product is a new product that people don't really understand, or it's a new concept that you have to explain, that's just the case in some products.

If it's a new thing that's part of why you're innovating and building a new company.

Grant: Category creation.

Bob: Yeah, if you're doing category creation-- I'm sure maybe somebody could find an example of a low-friction sales model for a new category, but I'm skeptical.

So the simpler the product, the simpler the buying decision, the lower the price, the narrower the audience, the more you go to the zero-touch side.

But if you're solving a hard problem that involves a bunch of different people and you're being part of transforming something inside a company, sometimes it's just going to be a heavier weight sales process. That's OK.

Grant: Sure. I think the interesting piece here is that the framework is not "We're leveraging the pool." It's like, "OK. This will give you the insight. Look at the decision process for buying--"

Bob: You can change your product and change the problem you're solving because you want to steer it a certain direction. Now, you have to validate that that's actually going to work. But yeah, you can steer it.

Grant: But generally people need to know if they have a product.

Bob: You have to be intellectually honest about what's actually happening in the market when people buy your product.

Grant: If you go through this exercise and think about like, "What is the--?"

Bob: "What is the cognitive process for how they decide?"

Grant: Then you'll get an answer.

Bob: Right.

Grant: That answer, you can lean into it if you want to keep your exact product.

Bob: You can test different things. I could say, "Let's test the high-velocity model. Let's test the online eval followed by inside sales. Let's test the up the middle and let's see what works."

You iterate on go-to market the same way you iterate on product.

Grant: That's interesting.

Bob: Yeah, that was interesting aha for me is you iterate on go-to-market the same way you iterate on product.

Grant: How do you do that? How do you track? How do you think about that?

Bob: How do I think about that?

Grant: Yeah.

Bob: This gets to "How do you build your go-to market playbook?" This is a really important concept that frankly, as a first time product-oriented CEO in 2009, I was completely ridiculously wrong about.

Rewind to -- Actually, this probably late 2009. We had our first product in the market, winning our first customers, we're trying to unlock growth and find repeatability.

I had hired two sales folks and then hired a VP of sales, and my new VP of sales was like, "All right. We need to build our go-to-market playbook." In my head I translated "Go-to-market playbook"to "That means a good PowerPoint pitch."

Grant: Go-to-market pitch deck.

Bob: Yeah, "I need a good pitch deck." Now in the rear view mirror I realize how ridiculously wrong and naive and narrow minded that view was.

If you think about the go-to market playbook, it's how do you repeatedly find and win customers over and over again? When you first find them, what do you do?

What's that journey the customer goes on, and you have to walk them through from the very first time you find them and connect with them all the way to the way they make the decision?

It's not, "I've got a good PowerPoint presentation." A PowerPoint presentation might show up somewhere in there, but it's like a bullet on a list somewhere.

So, how did we figure that out? Ours started by accident on a guy named Mike Lee's whiteboard.

In the very beginning of finding go-to-market repeatability and finding go-to-market fit, one of the problems is founders can't find go-to-market fit and founders cannot find go-to-market repeatability, because inherently the founder selling process is not repeatable.

Founders have magic pixie dust. You can get meetings that nobody else can get. You can say things in meetings nobody else can say. You could be like, "Here's the 27 things we could do." You commit to stuff in meetings, it's totally not repeatable.

So ironically, finding repeatable sales motion, if the founders trying to do it you're getting all sorts of false signals. What's the answer to that?

I actually recommend that you need to hire more like a Davy Crockett, a couple early sales reps or marketing people to find the path through the woods and iterate and try stuff.

Try this, try this problem, try this message to iterate on it. One of our Davy Crockett--

Grant: What are the skill sets of a Davy Crockett? How do you find one?

Bob: Yeah. Mark Leslie also, interestingly, has a thing he wrote called the Renaissance Sales Rep. Similar thing, I call them "Davy Crockett"because I think the metaphor of finding the path through the woods is descriptive.

Grant: Yeah, sure.

Bob: They tend to be like 60% sales, picking up the phone and going to talk to people and pitch, and 20% product marketing and 20% product management.

They tend to have a little bit of marketing bones in them and they also have a little bit of product bones in them, because they go meet with customers and they try things.

"Try this, try that. What about this problem, what about that problem? If we can't help you with that, what about that?"

They're iterating, they're testing things and they're making stuff up, and that's OK.

Grant: This sounds like a founder.

Bob: Yes, but it's a normal salesperson.

Grant: Right. That's actually the interesting thing. These people are potentially good founders at some point, and to have a little bit of that "Discover the problem--"

Bob: They've got to explorer gene in them.

Grant: But they're not the founders, which is really important in this case.

Bob: Yeah. Typically a product-led founder built the product or the vision. One of our early Davy Crocketts was a guy named Mike Lee, Mike had a whiteboard in his office that--

Picture this, he's just trying to get customers to keep talking to us. All right, he had this list on the whiteboard that on one side was the stuff that seemed to work to get people to keep talking to us, and stuff on the other side that was like "I thought this was going to work, but it wasn't going to work."

He just did it for himself, because that's what he's trying to do, he's just trying to figure things out. It was interesting. Then the rest of us started to pay attention to Mike's whiteboard.

"Wait a minute. That worked? That's interesting. What do you mean that didn't work? We worked really hard on that. We're offended that didn't work."

That became the real world test chamber for what we thought was going to get customers to keep talking to us, which in some ways is the very early part of building your go-to-market playbook.

"How do you get a customer to talk to you once? Talk to you twice? Talk to you three times? Engage? Do an eval? Spend time with you?"

Grant: OK, the things that showed up on his "people we'll talk about," this--?

Bob: They're willing to spend more time talking to you, because if customers are willing to spend more time with you it's at least a signal that you're onto something. It's important.

Grant: So iPhones was on the "They will talk more about iPhones" list.

Bob: Yeah. They were like, "Tell me more about that." Exactly.

Grant: But some Windows phone, they were deaf to, right?

Bob: Yeah. It just was less interesting. There's other things that we thought were going to be important that weren't too.

Grant: You're trying to basically sound like you're building this catalog of different things that you can then--

Bob: Needs and problems and stories, and who they're talking to. It's iterating on who the ideal customer is, "How do you get their attention, what do you do in a first meeting, what happens in a second meeting? How do you get them to an eval? In an eval, what are they doing?"

You're basically starting to build this customer journey. So what does a go-to market playbook look like? If you envision across the top you have the steps in the customer journey.

If it's a heavyweight sales model it might be like, "Marketing does lead gen qualification, hand it off to inside sales.

You have a first meeting and you have a second meeting, you have an evaluation, you have a decision meeting, you have a win and they have onboarding.

Whatever, like 5-6 steps. Under each one of those, you have "What are people doing and saying in each stage?"

Or if it's a marketing led sales model, you've got like, "OK. Messages with CEO and SEM, how are you getting people on the landing page? What is some online video content that you're doing for education to get people more engaged? How are you nurturing them? Oh, you get them to an eval. Great, and eval. You get eval onboarding."

You could start to figure out building this musculature for "What is step one, step two, step three, step four, step five on the customer journey, and what are people doing and saying at each stage?"

That is what becomes your go-to-market playbook, and I had one company I was working with that they showed me their go-to-market playbook and it was like 50 pages.

I'm like, "That's not a go-to market playbook. That's a brain dump of everything you've ever learned." A go-to market playbook, like ours fit on one page.

It was one PowerPoint slide, maybe two, but it's the distillation of it down to the essence of "What's the customer journey, what are people doing and saying at each stage? What's the rest of the company doing to be able to support each one of those stages?"

How you figure this out is as you're in your early customer engagements, pay attention to not just your wins, pay attention to the losses.

Why did you lose? Why did a deal go fast? Why did it go slow? Why did a deal disappear? Why did it get big? Why did it get small?

Those are the universe giving you feedback about what's working and what's not working to help build this go-to-market playbook.

You'll discover things in there that become part of your go-to market motion, and there's something I call the "Wows."

Which is when you're in a customer meeting, I'm sure you've been through this, anybody who's tried to sell new products, you go to sit down in a meeting and a customer and you go "Blah, blah, blah."

You're going through your pitch and there's something you talk about where all of sudden the prospects' body language changes and they stand up or they lean in. They're like, "Wait. Tell me more."

Grant: Perfect.

Bob: That's a clue that you're onto a "Wow," which is something that got their attention that makes them want to spend more time with you.

Those are really important to find those in your early part of your go-to-market playbook. Like, "What are the things that cause customers to go "Wow, I want to spend more time with you."

Sometimes there's one, sometimes you can find two, sometimes you can find three. But the trick is-- It's funny, as a product-centric founding CEO you always think you know what the "Wows" are.

Or your product team thinks they know what the "Wows" are, your engineering team thinks they know what the "Wows" are. The funny thing is you don't get to decide.

I didn't get to decide, your customers decide. The weird thing is, sometimes the "Wows" are not what you thought they were.

You of course intuitively imagine it to be the thing you worked the hardest on, and that you're most proud of.

Grant: The most complex engineering problem in the background.

Bob: "Super exciting. This is hard."

Grant: There's a dag back there that's deciding what's happening.

Bob: Yeah, "We have this really awesome big giant policy engine that helps you do blah-blah-blah."

Often it's something that could be even smaller than you thought, but customers go, "Wait a minute. Tell me more about that." Keep your eyes open for those, and the customer gets to decide the "Wow," not you.

Be prepared to be a little offended because sometimes it might be something small, but that's OK. I'll give you an example.

For us, one of the "Wows" in the early days was when we were pioneering Bring Your Own Device.

We invented this concept called selective wipe, so we would walk in and be like, "We have this product that helps provide security and management for any mobile operating system to help you embrace mobile as a first class citizen."

We were really excited about our big giant security and policy engine, and the customers were like-- We'd show them this ability to wipe your work stuff, but leave your pictures and music alone.

They'd be like, "Wow. Show me more." It was a cool feature, but it wasn't that hard to build. It felt like, "Really? Is that what it is?" Ironically, we actually buried the feature down in our UI because it was logically located where it was supposed to be, but we buried it a little bit.

Grant: Employee off-boarding.

Bob: Yeah, exactly. It was down there.

Grant: De-provision that user.

Bob: Exactly. It was like, "Wait. That's actually a "Wow" feature.

The funny thing is, at the time, most customers didn't even have BYOD. If we had measured that feature on usage, we would've gotten a totally false signal.

That was a super important feature to get customers. Keep talking to us, engage with us, keep moving. That was definitely a "Wow."

But if we measured it on usage, then we've gotten a totally false signal. I'll give you a second "Wow." Again, this was something that came from meetings with customers.

Grant: That last one, did you think it's because that's where the market was eventually--?

We have hindsight now so eventually everyone's going to BYOD, and that would become a thing that would enable BYOD, because now you could selectively wipe.

Bob: There was an element of being ahead of the curve. Sometimes when you're ahead of the curve that's a capability that gets people to want to spend time with you, engage with you.

It's part of the reason they buy your product but maybe they're just not going to use it yet. Interestingly.

The second "Wow" for us had very similar characteristics, which was we invented a concept called the Enterprise App Store.

Everybody was used to the app store in the consumer world, we built the first enterprise app store for companies to be able to deliver apps to their employees phones.

Grant: Like, internally develop apps?

Bob: Yeah, internally develop apps for app store.

Grant: Very cool.

Bob: It was a killer demo. "Wow." The funny thing is, no customers had any apps. But again, if we had measured that based on usage--

Grant: But everybody wanted an app. They wanted an app.

Bob: It was aspirational.

Grant: Yeah. "We want to have an app that's cool." Everybody has an app idea.

Bob: "We're going to have one some way, someday."

Grant: Every IT guy has got some app idea, they're going to app this and there's an app for that.

Bob: There are definitely capabilities as part of the go-to market playbook that we'd show and the competitive evaluations, things like that, that were much more usage-based.

But the thing on this is there are certain things where the customer's body language changes, where they're going to want to spend more time with you.

They get decide where those are. Build those into your go-to market playbook, draw a big circle around them.

Sometimes you have to redesign your product to elevate the "Wows." It's OK if it doesn't get used.

Grant: Yes. This is actually interesting, because the "Wows," should you use that as signal for "OK, let's build more features around selective wipe and make this a really big part of our product set?"

Or should you be like, "OK. It's a it gets everyone to go "Wow," But the real value is in all the other stuff we do."

Bob: The answer is "It depends."

Grant: OK.

Bob: In some cases the "Wows" may just stay isolated little "Wows" that are just are exciting things that get people to keep talking to you.

Sometimes it's a precursor of things to come that becomes an end to end set of capabilities that customers use over time, and it's just early. I've seen both.

Grant: OK. As you're getting that feedback, someone's like "Wow, that's really amazing." But they're not using it today, so you keep it on the radar as a thing.

You're like, "Look. People still really like this. Let's make sure we don't ignore it. Let's put it up higher in the products with more exposed, and then it maybe as people start using it more we start to dig into actually building features around it."

Bob: Yeah. I think you could see that like as it starts to get really adopted, then you start really building the workflows around it and expanding it.

I think, particularly if you look at a go-to-market playbook where you're driving customers through nurturing to online demos and self-driven evals, being able to have the customer to be able to discover the things that they go "Wow," and they want to spend more time in your demo.

Things that keep going, especially in a self-driven demo and eval world, you have to be super deliberate about what these "Wows" are.

Then that gets to the next part of the go-to market playbook, which is "OK. Once you get the customer engaged, how do you get them across the line?" In many cases that involves an evaluation, a POC, things like that.

Being really deliberate about what that part of the experience looks like and what are the supporting tools and things you need to be able to deliver to your go-to market team to be able to do that.

I'll give you an example. For us, when customers would go into an eval mode, we would drive customers to eval. Like, "Mr. Customer--"

Because that's a sign it's a real deal. They are willing to spend time with you. Maybe they're bringing in competitors, like it's go time.

You have to be able to build a repeatable process for evaluations. Now, what's funny is in the early days of markets, customers often don't know how to evaluate products.

They just give themselves a left to right UI tour through your product and it's like a random walk in the woods.

The one thing we realized, "Wait. We could actually tell the customer what to do and how to evaluate the product," which is an awesome place to be.

We ended up creating this Excel spreadsheet that basically was like, "Here's the 10 things you go test in an evaluation, Mr. Customer. If they turn all are green, of course you buy."

You get to set the table. You'd be surprised in a lot of cases, particularly in newer category creations, customers don't know how to evaluate the products. You get to set the table for how evaluations happen.

The second thing is that sometimes you can stick stuff in there that becomes competitive traps. Which is, if you think about your go-to market playbook, there's often an evaluation guide or a self-driven demo or self-driven eval.

Get really prescriptive about that and you're going to put stuff in there that, "Of course, if you get to these 10 things and they all turn green, you should buy." But you could also stick second order things in there.

This is one of the things I learned, was you can stick second order capabilities or tests in there that aren't actually that important in the grand scheme of things, but you know your competitors are going to be pissed about because the customer's going to ask your competitor about X or Y and they're going to be like--

And they're going to try and do the same thing to you. This is where the hand to hand combat happens in the go-to market playbook, is in this eval/POC stage.

"How do you define the decision criteria? How do you set the table for the customer, and how do you lay traps?"

Grant: Yeah. That's a really important part of the go-to market, is understanding if you're early in a market you can set the--

Bob: Decision criteria.

Grant: The expectations, and you can deliver that to your customers, and then you're just producing it as an asset. "We distribute this along, take a look."

Bob: It became part of your core training for your sales team, your go-to market teams or for your marketing team to build the online evals.

You have to get really prescriptive about it and it becomes very cross-functional. It's your product team, your marketing team, your sales engineers.

This is where the collective IQ of the company, in many ways, about what's winning and losing deals--

This is the sharp edge of the sword on the ground inside customers deal by deal by deal. So, yes, you have to get really deliberate about it.

There's a feedback loop there as the market evolves, you're like, "There's something new we're seeing in the market. We've got to change this part of the go-to market playbook," and then you've got to get everybody on board with changing it.

The go-to market playbook becomes the core operating system for your whole go-to market motion. It becomes like muscles. That was the thing that was amazing, is when you get the go-to market playbook right, and you get the urgency in the sales model defined, the way you know is you just start to feel the momentum. You put more in, you get more out.

You start to feel the momentum and you can hire new salespeople. They know what to do to win deals.

You add channels, you've give them the playbook, "Here's how you win deals." You add somebody new in marketing, "Here's what we do."

As you start to get that machinery going and that playbook going, it's magic, because you start to feel the momentum and it becomes like muscle memory.

Now, there's an interesting side story to this. Over time you need to evolve and change your go-to market playbook.

Grant: Right. I was thinking about that. Because markets change, other things happen.

Bob: Or you add a major new product capability. Ironically, the power of getting go-to market fit and you're going to market playbook is the repeatability of it.

The challenge of it is when you need to change it, you have to rewire muscle memory that's gotten built into your team, where it's almost subconscious.

Making changes to your go-to-market playbook and the way your team goes to market is not that easy.

We've got an interesting story there where 2012 MobileIron we had probably 1,000 customers at this point. We really had a go-to market playbook cooking.

Grant: Yeah, sure.

Bob: We went from selling one product to selling a platform with three different products and an ecosystem. That was a fundamental change to our go-to market playbook and I totally underestimated that. We basically created the pitch, rolled out some training, went through it--.

Grant: Training internal--?

Bob: Training internal, new website, new pitch, new demo and stuff like that.

Grant: You had all the collateral.

Bob: All the collateral, we did a bunch of training. Then six days later everybody just went back to doing what they were doing before.

It was frustrating, and I think changing your go-to market playbook, it's like unlearning major muscle memory and re-learning muscle memory.

It takes a little bit of shock and energy to be able to do it. I was frustrated and the team and I were struggling with what to do, we were like "All right.

Should we just repeat what we did before and just do it again?" We decided to do more of a shock therapy.

We basically made every single sales rep and every single sales engineer present the new pitch to me as CEO, one on one, and get graded.

Grant: As if you were a customer?

Bob: As if I was a customer. It absorbed two weeks of my time, which you could argue maybe wasn't that efficient, but what happened was it sent a signal--

"A) This is really important. Please spend time on this," and we've got a chance to see who is really good and who wasn't as good at making the change.

That level of intensity around rewiring your go-to-market playbook is almost what's required.

I think you see a lot of companies stumble at this when they go from selling a single product to multi-products, or they've got a major shift in what they're doing.

They just stuff it through the go-to market playbook that they built that was working, and they're like, "It doesn't work and it's hard."

It took us real shock therapy for ourselves to rewire our go-to market playbook.

Now fast forward 90 days after that, we started cranking. Fast forward a year, 60% of our sales came off the new products and new platform capabilities that came out of changing that go-to market playbook.

Grant: I'm guessing that process where you made everybody pitch you, there was probably a bunch of feedback that happened, and I'm guessing some iteration. Because they're like, "Here's why I don't do it that way." Is that right?

Bob: In many ways, like when we did the rollout number one, we had a lot of feedback that came in as part of rollout number one. Then there was a painful relapse period.

Then we did the more intense shock therapy to rewire how we went to market. There was a lot of feedback. I learned a lot from listening to everybody tell the story.

I'd be like, "That didn't work very well," or "That was really good." Actually, it's a great example where there was one woman who was a channel sales rep in Europe who absolutely just crushed the new store.

It was better than all of us. It was like "A) Keep an eye on her. She should get promoted." We're like, "We're going to adopt some of the things she said." It was part of that rewiring, you learn how to get better.

Grant: Had you rolled it out to a small group of salespeople?

Bob: No, we rolled it out to everybody.

Grant: You did it all once? OK. Do you think that's the right way? Looking back? Or should you have gone a little bit more--?

Bob: Yeah, probably. Maybe we should have piloted it a little bit more.

Grant: Yeah. Moving fast is what you have to do. It's a balance.

Bob: It's funny, I made the same mistake. Remember in the beginning I said, "Go-to-market playbook is like having a good PowerPoint pitch."

I made that same mistake again where it's like, "OK. We've got a broader platform and eco system, we need a new pitch." We rolled out the new pitch and we were like-- that didn't work.

We had different competitors we were competing against, we're now selling, there's different people inside the customer involved. It required a change in thinking.

Grant: I feel like you almost need a Davy Crockett-ish salesperson on that when you first roll out a new product.

Bob: That's a good question. I think there were early adopters in your own team that naturally didn't try and take it, and I think that was--

I'm thinking about this on the fly because it wasn't just me, I was obviously the head of product and the head of marketing, but everybody and head of sales was involved in this.

As we're into alpha and beta and all these new capabilities, it was really expanding our product platform. There were people who were that-- Essentially the Davy Crocketts for phase two of the company.

Grant: Yeah. They went out and talked to early customers, came back loyally, feedback out, feedback in.

Bob: I think there's a macro point here, which is that you can be really successful in act one as a company, and it's hard to be successful just for act one.

I think I underestimated as we were trying to make the transition to act two for the next version of what MobileIron was going to be.

The broader story, the broader platform that drove our growth. I think I underestimated the internal rewiring it took for our go-to market playbook to be able to change from act one to act two.

I think if you look at the great companies, very rarely do they become great companies just on act one, it's usually act one and act two and even act three that allow companies to become the $100 million, $200 million, $300 million dollar a year really successful businesses.

Very rarely is it just whatever the one thing is that got them off the ground in the beginning.

Grant: Yeah. You have to reinvent what you're offering, you have to think about how you're talking about it.

One thing we were talking about before the podcast started is fast moving markets. If you think about the mobile ecosystem ten years ago, that was the epitome of a really fast--

Bob: It was total chaos.

Grant: Yeah, exactly. Android coming out--

Bob: It was total chaos. Nobody knew how it was going to evolve.

Grant: I think you have a little bit of a framework for thinking about this, so I'd love to have you share how to find the market trends that you--

If you want to keep calling it correctly the whole time, because calling mobile in 2008 was a great call, how did you call in the--?

Bob: Mobile 2010 looked very different than 2008, and mobile 2012 looked very different than 2010. Yeah, that's a great topic.

This idea that for companies to really become successful platform and long term businesses, there's an act one, act two, act three. As a result, you have to call the ball about what are these evolutions that happen in your market?

Because if you're in a fast moving dynamic market, it's going to evolve, and the trick is how do you evolve with it and stay ahead and in front? So how do you call the ball?

I think one of the backstories for MobileIron that I don't think we probably really talked about is that we successfully called the ball five or six times in a row for how the enterprise mobility market was going to evolve.

Enterprise mobility in 2008 was really different than 2010, 2011, 2012, 2013. It was a really fast moving market. We called the ball right a bunch of times in a row, so part of that was probably luck to be fair.

But one of the things we did that I think really helped, and we just totally stumbled into this by the way, it wasn't any massive foresight.

But we started doing this thing we called our "Market thesis." Just for context, every quarter we'd get together as a team offsite religiously, and I totally recommend that by the way.

When things get really busy and it's going to be hard to do, do it anyway.

Grant: How many days?

Bob: At least one day, sometimes two.

Grant: Cool.

Bob: "Off site goals, what's working well, what's not going well, how are we doing? What are our goals for next quarter, and what are some big topics to talk about?"

You just need quality time together as an executive team, and it's hard to do. Everybody's going to be really busy, including me, but we just had to be religious about it.

It was really painful sometimes but I'm really glad we did it. One of the things we would do at these off sites, not every one, but probably like every other one we would do this thing called a "Market thesis."

Which sounds boring, but turns out to be really powerful. Basically, what we do is I'd ask every one of the folks on my leadership team to go spend some time by themselves ahead of the meeting and write down what they think is going to happen in the market over the next twelve months.

"What's going to happen across customers? What's going to happen across product? What's going to happen across competition? What's going to happen across our ecosystem?"

Grant: So everybody goes separately?

Bob: They go do it themselves ahead of time, write it down. We'd create this for our block during the offsite where everybody would basically present their piece to everybody else, like one slide with these four sections on it, and everybody present everybody else.

What ended up happening is sometimes all of a sudden you'd see everybody start talking about the same thing and you're like, "OK. Wait a minute, that's a big deal.

Everybody's seeing the same signal." Or sometimes you would see something come from one of the folks on the leadership team that nobody else had seen or heard about.

We're like, "Wait a minute. Tell us more about that." All of a sudden we'd be like, "Oh, my God. That's a really big deal. We got to totally figure that out or get on that."

I think in retrospect it was a way to really pull out all the conscious and subconscious market signals, observations, customer conversations and internal conversations into a way to share with everybody.

You could start to see the patterns, and a lot of the correct times for us calling the ball about what we need to do next.

Sometimes what we didn't need to do next came out of those discussions, and like I said, it's got a boring name, "Market thesis."

But I think that collective wisdom and forcing that discussion in an organized way turned out to be one of our secret weapons for calling the ball right a bunch of times in a row.

Grant: Yeah, I love that. I'm probably guilty of going down the path of being a little too top-down or working with my co-founder just the two of us behind the closed door, trying to--

Bob: Then it's all on one person to synthesize it.

Grant: Yeah, exactly. I think really going your team, having everyone do this, letting everyone--

Bob: Especially now that-- we're now like 2-3-400 people with 1,000 customers, the market is moving fast. Being able to synthesize this and figure out what to do is like--

I suppose I could have just decided or the product person decide, but it's probably not going to get to the right answer unless you are a genius or lucky.

Grant: Crowdsource is-- it's even better. You come across these really smart people, and then everyone's more engaged with it because they helped build the market thesis.

Bob: Then, because we're doing this in our off site, the takeaways from that discussion often was very easy to then turn into goals for the team.

"OK, as a result, what do we got to do as part of our goal planning for the next six months?" Or "Crap. We've got an issue we've got to resolve, let's figure that out."

It was very tightly tied to the, "What do we then go do about it?" Or "What do we then not go do about it?"

Grant: Sure. I'm going to bring it back real quick to EnterpriseReady. We have these features that we talk about and it's interesting to think about the set of common features that are never really going to be a "Wow" probably, but where do they fit in in terms of this company evolution? B etween--You're not doing an ideation phase. You're not like, "We're going to have the best product log--"

Bob: That's market-specific killer features and capabilities that are very specific to your problem, which is why the customers buy your product. Exactly. But then there's a bunch of stuff that's table stakes.

Grant: Where do those fall in, and where should you be thinking about adding those in? Where did you guys add them in at MobileIron? Maybe that's a good framework.

Bob: This is actually one of the hardest parts of being the head of product or engineering in a fast growing technology company, is actually making those trade offs.

The way it ends up feeling is that very rarely is a customer going to buy your product for one of these EnterpriseReady features like reporting or auditing or single sign-on or role based access control.

No customer is going to be super excited about buying your product because they have that. It's all about the other stuff. In some ways it's actually the way things become, the reasons why somebody may not buy your product or they may wait.

But in the early days of a market and product, customers are willing to cut you some slack on that stuff.

It's a tough trade because what ends up happening is you have a limited amount of engineering resources and you're like, "All right. Do we do A, B and C to change the market? Do A, B and C to generate new revenue? A, B and C to change the customer conversation? A, B and C to compete better? Or do A, B and C to do something that nobody is going to talk about, but if we don't do it maybe they won't buy?"

That's how it manifests itself, and what ended up happening, and it came in fits and starts, is that periodically we'd carve off a block of product energy and R&D energy to knock off one of these enterprise features.

It could be role-based access control, but it took us a long time to get to it. But once a year we'd carve off a block to say "All right, let's go knock off one of these things."

It was one of the toughest jobs of being the head of product was balancing when to do that. Some of them probably took us four or five years to get to. It was interesting.

It's a judgment call about listening to your customers about what's really going to drive their purchase decision, and then what's really going to drive their adoption. As long as you're listening to those things and factoring correctly, that will naturally drive the prioritization of some of the unsexy but important Enterprise Ready stuff.

Grant: Yeah. To your point, I think this is also true when I talked to the Segment founders, sometimes there is just so much pull for your product and there's so much urgency that--

Bob: You can get away with it.

Grant: You just get away with it.

Bob: Customers are willing to give you a pass for a while.

Grant: Yeah. Our thesis was always--

Bob: Or sometimes it's the size customer you're selling to, by the way.

Grant: Of course.

Bob: Mid-market, you can get away with it if you're going to sell to Morgan Stanley.

Grant: As soon as you're going into an enterprise and you need these features at some point, the one thing that I always think is a great point too, to your point you can get a pass on some of these features.

Knowing what they are is really helpful, being able to talk to them and say, "We understand you need role based access control. Here's why you need it. It's important to us that you be able to do that at some point."

Say, "Obviously we think, currently, can you work around this in some way for a while before we have to build this in there?" You can get that pass. Four or five years might be a long pass, but that's what it takes sometimes.

Bob: Yeah. In some ways, I think because of the speed and urgency around the evolution of the mobile market there were so many other things changing.

iOS came out and Android came out, and the releases of software every year, and then "Wait, there's apps content."

The rate of change of the market we were dealing with was absurd. Just keeping up with the eco system changes was an enormous amount of energy, and customers actually told us "That's the most important part for us."

I think in some ways we probably had a different experience than some companies, because of the sheer chaos and rapid evolution of the market. The most important thing to our customers was to keep up with that.

Grant: Yeah, because it's just, "There's a new OS, it's coming out. We need to have support for it."

Bob: If you don't support it day one, that's a real problem. That's mission-critical problem.

Grant: Because of the speed at which everything underneath the hood was moving, they were willing to sacrifice a few of those other features.

Bob: I think in some ways we probably waited too long on some of the Enterprise Ready features. I think in retrospect, there's some that we'd probably do differently and do earlier.

Grant: Any in particular come to mind?

Bob: I think role-based access control took us longer than I think we thought, and my one piece of advice for founders and early product folks thinking about some of these things is that some Enterprise Ready features have architectural implications, like roe-based access control.

Some enterprise features, like reporting, don't. The ones that have architectural implications, it's important to think about them earlier.

Grant: Yeah. At least to plan.

Bob: Because they get harder as time goes on.

Grant: You end up accruing more technical debt over time as you don't have them, because you need to get them in and it's hard over a bigger code base.

Reporting is one of those features that ends up sometimes helping you sell.

Bob: Reporting is in many ways how you manifest the value proposition for your product, and there's tons of examples where reporting, "Really? Is that sexy?"

If you put yourself in the position of your customer, they've got to go to their boss to justify what they're doing. That is often what they show.

The second thing that don't underestimate that I've seen a couple of times with a couple of companies, is something that gets generated out of your product and report that gets used by your customer, they send upstream as part of their operational report.

If you, during a POC, can get one of your prospects to embed some of your report information in something they send up to their boss, the likelihood of them unhooking you after they've already started to send that information upstream gets lower and lower and lower.

Reporting can actually be a very strategic part of getting embedded in your customer's operational workflow.

Grant: Yeah, that's a great point because whoever they send it up to is going to ask for it again, and they'll be like--

Bob: "I decided not to send that to you now because I decided to say no to the product."

Grant: Yeah. "But I want it back." They'll re-implement everything just to get that one report back if their boss needs it.

Bob: The trick is knowing which ones those really are. I think you can go down a lot of rabbit holes about things you may think are important, but it really comes down to putting yourself in your customer's shoes, talking to them, watching them.

"What are they really sending upstream?" To really understand, "How do you make them the hero?" That usually is what it comes down to, is "How do you make your buyer or your decider a hero?"

Grant: Yeah, that's so important. If they can get a promotion based on using your product, and that's part of what reporting does.

It helps them present things up the stream to make them appreciate the work they're doing.

Bob: Totally. I think every once in a while you're part of a new category creation or a new problem that gets solved where your customers end up making their careers, or get promoted on the backs of whatever they learned how to do with you.

I think that's actually one of the more satisfying things about when I look back on our 12,000 customers at MobileIron was that mobility was new.

There were a lot of our early customers that got promoted because they became the woman or the man that made mobility happen inside company A, B or C.

Or like at Marketo, there were marketing managers that got promoted as CMO because they were the ones that made marketing analytical.

In the early days of Cisco and networking, like the people who made the internet happen inside companies became the CIO.

So don't underestimate the impact that you and your product and what you're helping your customers do can have on their careers.

That's a very profoundly satisfying impact you can have, not just on your customers businesses, but your customers' people and their careers.

Grant: It reminds me, we're talking a little bit before about why you should build enterprise software companies, and I think a lot of it is because we spend so much time at work.

You can really impact people's lives in a really profound way. 40 to 80 hours a week we we're doing these things, so you have some perspective on some other reasons why and some opportunities you see changing. I'd love to hear--

Bob: It's funny. I've been doing enterprise tech since, I guess since 1992. For a long time it was considered pretty uncool.

Grant: It's so cool now.

Bob: Consumer was so much cooler. What I love about doing enterprise and B2B stuff is that if you look what's happening right now, the entire enterprise tech stack is getting reinvented.

Obvious stuff like the transition from prem to cloud. But that's a huge change. The entire app stack is getting transformed from traditional client server to web-based models to now container-based models.

Identity is being completely rethought, the Internet of Things is changing how people think about connectivity. There's so many things that are in the process getting completely reinvented.

Then you layer on things like AI and ML, so that's a multi-trillion dollar industry where a huge chunk of it is actually getting reinvented over the next 10 years.

I think that's cool and there's a great opportunity to build so many great businesses in there and really make a difference in our customers' businesses.

Like you said, we all spend a big chunk of our life at work. If we can help make those businesses and the people inside those companies jobs a little easier, or a little better, more productive, more effective-- That's adding value to the world.

Grant: I love it. Bob, I know that you're working on your next book, which is about--

Bob: Yes, Change or be Changed.

Grant: Yeah, the evolution in the role of CEO. I'd love to just close out by letting you talk for a few minutes about what does that mean to you? Tell us about the thesis behind it.

Bob: Frustration is often the mother of inspiration. One of the things that I think for enterprise entrepreneurs, or just entrepreneurs everywhere that is hard is as your company changes and grows, your job changes and therefore you have to change.

Or frankly, you get changed. I think there's the silent struggle that we all face continuously, which is "How do we keep up with our company?"

For me how that felt was, over the course of five years we went from me and like 20 other people trying to build a product that people cared about to 500-600 people doing $100 million dollars a year thinking about going public.

That was a crazy five years, and over that period of time I think one of things I didn't appreciate is that as the company changed, my CEO job changed.

For my leaders, their job changed and for their teams, their job changed and for my board, their jobs changed.

I don't think we spend enough time, or there's not a lot of institutional knowledge passed down about how as companies change people's job change and they have to change themselves.

It gets thrown around in these memes like, "Go scale." It's like, "What does that mean? Nobody knows what to do with that."

My core lesson on this was unlearning, which is the irony is the things that I think helped make me successful as the zero to 50 person CEO trying to find product market fit got in my way becoming the CEO of the whole company, trying to unlock growth.

Then things that made me successful there got in my way at the next level, and so we spent a lot of time talking about what we need to learn and I think that's important.

But I don't think we spent enough time talking about what we need to unlearn, and for me as CEO, the first CEO job felt like Captain America or Wonder Woman with a platoon in the woods.

It's like you're throwing punches, taking ditches, getting dirty, it's a blast. But then the second CEO job was more like The Avengers, where it's like you have to hire a band of superheroes, each of which who has a better superpower than you and you have to let go.

Otherwise they're not going to come work for you, or they're going to quit. You're hiring somebody that's better at sales than you, and marketing than you, and product than you, and sales than you.

Of course, that's the right answer. But what's the first thing they do when they come in? They look at all the stuff you worked so hard to build and they'll be like, "That stinks." So this change from being the CEO and the platoon to the woods, Captain America or Wonder Woman over to the Avengers is a hard transition.

The things that actually make you successful being the jack of all trades, you have to unlearn because you got to let go and let your team do it.

Then at about 400 people the CEO job changed again, to be more like Professor X. Professor Xavier and the X-Men, where you're like the dean of a university and your teachers are your warriors bringing up the next generation.

I had to do a lot fewer things, but for a lot more people. I had to repeat myself over and over and over again, which drove me absolutely bananas.

I really struggled with that transition. I think it's because in the Avenger stage, I was like, "We talked about this. We decided, move on."

But the job when you're 500 people as CEO is part of your job is to be a signal generator, to keep everybody aligned on the mission of the goals and doing.

Guess what? That takes repetition. So, "Suck it up, Bob. That's actually part of the job." But I got in my own way and was judging myself saying, "That's non-value added work."

Because I was applying my filter and my value-added equation that I had developed in the middle phase of The Avengers to the Professor Xavier phase. I had to unlearn that.

I think this applies to every leader, right? Sales leaders go from Davy Crockett to more Braveheart, or like Eisenhower going from fighting on the battlefield to fighting from the war room.

Every leadership job goes through these same changes where what got you from A to B is going to either hold you back or kill you going from B to C, so you actually have to unlearn.

On one level, it's a very uncomfortable process, it triggers a lot of insecurity because you have to let go of the things you're comfortable with.

Even the way you feel like you add value, so there's these weird "Emperor has no clothes" moments, but it's also a spectacular personal growth opportunity and learning opportunity.

At least for me, I think it made me a better person, actually. It's like those big gnarly things in life like having kids, it's illogical and it's hard, you don't get much sleep, it's messy. But on the other side it's like, "I'm a better person for it."

Grant: That's cool.

Bob: Going through these same types of things professionally has the same type of impact, but it doesn't mean it's easy.

That's what book two is about, it's called Change or Be Changed. It's orderable on Amazon now and the theme is "Unlearning."

Grant: Cool. I love that topic. I feel like we fill our lives with podcasts and YouTube videos and books we are reading, and everything else to try to constantly add more information.

It's hard to-- You're right, you rarely think about what do you need to unlearn, and stop doing, and do differently in order to advance? Because you can't keep everything in your mind all the time. You have to make space for new.

Bob: New behaviors, new knowledge and not doing things the way we used to do them. It's hard, it's much more counterintuitive and insecurity-generating than I thought going into it.

Grant: Because you're like, "I'll just keep doing the same things that have made me successful. Let's keep going."

Bob: Which is a natural reflex. Particularly under duress, by the way.

Grant: Yeah, exactly. "Who has duress? Start-up founders? No."

Bob: The funny thing, the book series we called Survival to Thrival because in the beginning starting a company, which is where you guys are-- It's like your main mission is "Just don't die."

Grant: Right, always.

Bob: But then at some point when you find go-to market fit and start to unlock this repeatable growth, then it becomes about "How do you win?"

Ironically, the very things that you do in the "Don't die" phase now get in your way when you're in the "How do we win" phase. And yes, we do know "Thrival" is not a real word.

Grant: It's a great word. We'll get it in there eventually.

Bob: It's phonetically consistent, if not grammatically correct.

Grant: It's perfect. Bob, thank you so much. I really appreciate all your time. This was amazing. I'm very excited to check out the new book, and hopefully everyone will read the first book as well.

Bob: Best of luck to all the entrepreneurs and folks out there doing the hard work. Sometimes it's lonely, but you're not alone. We've all been through it and we'll all continue to go through it. It's part of the journey.