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APR 15, 2019 - 46 MIN

Sales Training Lessons from Wizeline, Pusher & PagerDuty

  • Sales

Heavybit’s Sales Faculty Chair Trenton Truitt, and Pusher’s VP of Sales, Brent Kasper, discuss executing a technical sales program, setting sales efficiency benchmarks, and ramping to revenue.


The faster you can ramp up your sales team, the faster you can hit targets and scale the business. But how do you time-box and focus your sales training program? Heavybit’s Sales Faculty Chair Trenton Truitt, and Pusher’s VP of Sales, Brent Kasper, sat down for a chat on executing a technical sales program, setting sales efficiency benchmarks, and ramping to revenue. In this fireside, these two seasoned sales executives help you:

  • Choose the right metrics;
  • Set expectations early; and,
  • Follow through with tactical insights.


Trenton Truitt: Hi, my name’s Trenton Truitt and welcome to Heavybit Speaker Series. Tonight, Brent and I are going to talk about some sales lessons. We’re going to focus tonight on sales rep productivity and how we measure some of those things you’re bringing on your salespeople. Brent, do you want to introduce yourself?

Brent Kasper: Thanks. My name is Brent Kasper. I’ve been in sales for over a decade. I started as a door to door salesman selling telephones, believe it or not, wearing out the soles of my shoes. I still have lifetime bans from some office buildings here in San Francisco. Then I jumped into Salesforce, where I spent four years. Then I met Trenton as I joined as his first sales hire at PagerDuty. Then we did the PagerDuty story for a couple of years, then did it again at Wizeline for the last three years, and then most recently joined Pusher a couple of months ago as the VP of sales.

Trenton: It’s been fun to watch Brent go through his career from individual contributor, to sales manager, to director, and now to VP. Congratulations.

Brent: Thank you.

Trenton: I know the Pusher team is excited to have you. Again, my name is Trenton Truitt. I started my sales career at a company called Parametric Technology Corporation, PTC. This is a while back, I learned how to sell on value, make sure you are maintaining your forecasts, getting high end organizations, MEDDIC. I cut my teeth there, then went to a company called Asera, was there for a few years. The Kleiner Perkins backed company.

Then Documentum, I spent seven years there, I started out as a rep then I was a player coach, and then a manager and then director and a VP. I loved that ride. I left Documentum and went to a company called Appcelerator. We produced a solution called Titanium that enabled, and still enables, mobile developers around the world to build native iOS and Android apps using JavaScript.

Then PagerDuty, that was a great ride for both of us. We can share some of the metrics there. Then from PagerDuty to Wizeline where we spent the last three and a half years building out. Wizeline is a, if you look at what Gartner might call it a “Near shore product development company,” and they help some of the biggest brands. Wall Street Journal, Fox, Coca-Cola, Audi, develop and bring products to market.

But let’s talk about how we met, right? This is a good story about how we met, and a good lead in to today. When I was running sales at PagerDuty we had two sales reps and Brent and the other gentlemen were the two reps coming on the first day, and it was the day before they were going to start. The two reps looked at me and said, “What are we going to have those guys do tomorrow?” And I was like, “We don’t have our onboarding plan together at all.” We put together an onboarding plan that afternoon and started from there. So, don’t do that. That’s the first lesson. Make sure you have a good plan.

Brent: On our side, we showed up, no one was at the office. The onboarding plan didn’t necessarily go off without a hitch. The first e-mail that usually gets sent off, “Show up on your first day around x, y, z time,” never got sent. Me and the other gentleman showed up at 8 AM, but it’s a tech company, no one got there until 9:00. I got a text message saying, “Go find a coffee shop. I’ll be there in an hour.” We did that, then we were on demo. We were demoing that same day to Home Depot a few hours later. It ended up working out OK.

Metrics of Onboarding

Trenton: Yeah. You learn from your mistakes, and learn from your errors, and we were all busy doing things and we just let that one slide. But now, we put together the onboarding plan. Walk me through what that was like for you as a rep coming on board. Because what we ended up doing was putting together an hour by hour agenda for that first week of what you were supposed to be doing. Then we started assigning metrics to that. So, maybe the team would be interested in what those metrics were and how we looked at that.

Brent: When I started at PagerDuty, and we did this similarly at Wizeline when we didn’t have a lot of data to go off of, what we did was as a rep you go in and you’re looking for structure. You get through some of the HR things and you start determining “What are the things that make your company uniquely yours?” Because you’re not necessarily going to go and say “Here’s how you ramp on how to do sales,” you’re going to more specifically ramp on whether it’s customer stories, product knowledge, meeting the people.

Oftentimes the goal of a good onboarding program isn’t necessarily to teach every single person everything, but more to introduce them to all the people that can go help them along the way. At PagerDuty we did a good job of that, which was the sessions weren’t run by the same person over and over and over again, but were rather done by a community organizer– A community approach, where you at least met the people who had the answers for you long term. That was a great networking opportunity for us, because coming from Salesforce you only interacted with salespeople. Jumping into a startup there’s a lot more reliance on other departments.

Trenton: One of the questions here is, “Who needs to be involved in the onboarding process?” The answer is everyone in the company. As we look at Heavybit organizations, the majority are smaller, one to 10 ish million in revenue and they’re bringing on their first sales people. The ideas, the information that are in the founders and co-founders heads and engineers on the team and everyone that has touched customers, we have to get all that on paper so people can learn.

The goal here is to make things as repeatable as possible, because when you can make things repeatable and if you will in onboarding then you can scale it. The marketing message is important to catch in the marketing team, understanding that a lot of the questions are coming from tech support. That the reps can answer on the fly. Objection handling that, “Why do we lose deals?” Trying to implement and understand that. What I like to call it is, “We have to raise the bar of institutional learning. The entire company has to learn from these things.” Walk me through an example of what you learned. At the end of day two you were demoing WD-40.

Brent: Yeah.

Trenton: I’ll never forget that call. What’s interesting is some of your technology depends on how fast you can put a rep on the phone with a client first time. That was one of the questions, “How fast can you do it?” Let’s talk about if it depends on the technology, depends on how many at bats you get. If you’re only going to sell three deals a year, you’re not going to be on that phone call alone maybe ever. This is going to be a lot of team selling. But if you’re doing a lot of high transactionals, and you get more at bat. Walk us through that.

Brent: Like you mentioned, it comes down to a little bit of your approach and the level of hire. If you have someone coming in doing inbound leads, they’re relatively low value, high transaction. You can get people on quickly, most people tend to learn faster by jumping into the proverbial pool and just doing. Wizeline was a little bit different. Highly enterprise sales with very large deals. For them to truly understand all of our offerings we spent a good month getting people in front of the right engineers to understand how we positioned ourselves versus someone like Deloitte.

Those were two different experiences. But at Pusher we’re a little bit more on the lens of day one, you can be on the phone. The technology is a little bit more complex than PagerDuty, but at the same time people are very familiar with the brand. You’re not necessarily talking to people who are cold prospects, you’re talking to a lot of existing customers and you’re learning that way. But you have to take a look at each individual product and where you’re at in the lifecycle.

Performance and Measurement

Trenton: Let’s move into performance and measurement, if you will, for a moment.
As you’re sitting, as you’re doing your model for how many reps, how long to onboard, how long the ramp is. You take the technology, obviously, into account. Are you going to have installed accounts versus fresh territory? You have to take into account what’s in the territory, what accounts are there. Anything else comes into mind, as you’re thinking about the first step of how long ramp should be? What goes in determining that factor? Four months, five months, nine months?

Brent: It’s going to come down to you taking a look at the business to date. If you’ve got five customers and it’s taking you two years to land those five customers, I wouldn’t expect a one month ramp. When you come in and you say “We’ve got 10,000 inbound leads and we’re being flooded with those, and our average sale price is a couple hundred bucks.” You can expect them to start closing deals theoretically in a couple weeks.

It’s going to take a look at the market that you’re approaching, and the key when you start looking at what happens, “What is a good ramp?” How do we– how do I determine if, for instance, revenue is not necessarily the right indicator to determine if someone’s ramping very well? Because people do ramp at different schedules. You start having to break that down into more measurable and more controllable things. Because ultimately what you’re looking for from a ramp, especially for salespeople, especially for technical people for the first time managing salespeople, you’re looking to go test work ethic. Who’s coming in here and doing the right thing?

You can break that down to whether that’s activities like phone calls or emails, maybe it’s providing written reports for customer feedback, because the majority of what they’re doing right now is assessing the market. Maybe it’s coming back to taking on a couple projects around figuring out who your customers should be, cleaning up some of the sales data. There’s a lot of small things you can go do to go improve or measure a ramp that’s not necessarily revenue based. Because revenue is going to be so intrinsic to what type of company you are.

Trenton: Revenue is one metric, another one would be logos. I’ve put reps on logo quotas at times because at this organization our expansion was rapid. I would say, “Let’s get them on the drug. Let’s get them started on our technology and they’re going to expand.” So they had, the reps had new logo quotas, and I wanted to be excited to go get that first deal on the credit card and go to the next one. Again, expansion. Let’s take it down a level for this for this group. Let’s talk about ramp for a minute and how you might model that.

You understand what you’ve seen in your sales process today, and you have to pick a number based on that data. Let’s pick a number of six months in this example, and you pick a number of six months and no matter what number you’re going to pick at first it’s going to be wrong. Your job is to try to decrease that ramp as best you can and make the reasons why you’re decreasing that ramp as repeatable as possible. Let me walk you through an example.

Six month ramp from January 1, we hire this person, to June 30th. What you’re going to find is, you start putting in numbers like zero in month one, zero revenue in month two, maybe 10% revenue on month three, 25% in month four, 50% in month five, and whatever the math difference is for month six to be at 100%. Month seven would be 100% going forward. Hopefully, I can’t see you all nodding, but hopefully that makes sense. Then what you do is, you have your team and you start applying the metrics to how they’re doing against those numbers.

The best way for you to get ahead of your number with the board and your CFO, etc. is to reduce that ramp. If you can reduce that ramp, you start getting ahead of your numbers.

If you model a six month ramp and you can get the ramp to four months, that’s what we had at PagerDuty. It was 0, 33, 66, 100. That is percentages of what the overall MRR quota was. Month one, zero. Month two, 33% of what their monthly quota would be. 66 and 100, and so forth. What do we look for to reduce that ramp? We look for activities. The number of trials they might have, the number of phone calls they’re making, the number of demos they have, the number of proof of concepts. We’re looking for conversion rates on each and every one of those, we’re looking at how long an opportunity is in each sale, is in each step of the sales process. We have to measure that.

You’re going to look at your entire pipeline from MQL marketing qualified lead to SQL sales qualified lead, to SQO sales qualified opportunity, and then your sales process starts. We’re going to measure that for all of the company. All of Pusher you’re going to have that. Then you’re going to measure each time, and percent conversion for each rep, and you’ll understand where people need to be tweaked. If you look at a six month, and we’ve seen this, when you hire individuals and you have a six month ramp everyone ramps a little bit different against your model.

Some people might ramp, they might be flat lined and they jump up on month five and then they ramp because they learn differently. Some might start and they jump right up and they stay flat the whole time, because they’ve got an easy deal or they get it faster. Some people are going to be going up into the right the whole time. But it’s important to have those metrics so you can understand how to coach them.

Brent: I also think it’s important to break down, because those are the things that by talking about flat line and going up is typically a revenue indicator. Who is going and closing those deals? That oftentimes isn’t necessarily, like you’re saying, rep controlled. Revenue is sometimes lucky, sometimes I say revenue is mostly rep influenced.

You can influence how a customer can buy, you can influence how a customer makes a decision. You can’t necessarily control some of those things.

The activities, the things that you talked about, are the controllable things. That’s what you’re looking for, a rep taking ownership of the controllables. Then documenting, the key about PagerDuty when we brought it from six months to four months was we documented every onboarding class that we did. You did exit interviews of what worked, what didn’t work, 90 days after that and after they’re into the business.

What things were they still looking for? Then 180 days afterwards, what things were they still looking for? We started going back and re-influencing the next onboarding class so that every single one got a little bit better. The questions got more and more refined, sessions got thrown out, sessions got added in. But that’s the key thing about a ramp. Ramp is an organic thing. It should never be built and left alone, it needs to always be being worked on.

Training Timeline

Trenton: It’s a good point about how your ramp doesn’t end, because you’re checking back in with people continuously and trying to understand what you did differently with one class against another to make sure you incorporate those things. When do you know when to let someone fly solo? Where in the ramp do you get a sense of, “Mary can do this on her own?”

Brent: It depends a little bit on the management layers that you have. Sometimes letting people fly solo is a necessity, because you don’t have the people to go sit with them on every single phone call. You hope for the best and there’s tools out there, like Gong, that can record calls for you. So when you do have that time you can listen to people, but it’s going to come down to once again, territory, size of the accounts. The value of those accounts.

I typically try to go get people on their first solo activities to do some of the more low value work where they can go talk to people who are potentially not the Nike’s and the Disney’s of the world. But let them go through and get their feet wet on a couple of the small opportunities. It’s a bit of a feel, I don’t subscribe to the concept of “I took a test,” or “I’m ready to go talk to people on my own.” The problem with that is, once again, people learn a little bit differently and most of the time curriculum based ramps are designed by engineers. The curriculum is, “Do you understand the technology?” Not necessarily, “Do you understand the problem or the value that we’re providing?” And someone who understands the technology isn’t necessarily prepared to go talk to a customer. It’s a bit of a mix, but it’s earlier than most people expect.

Trenton: This is a great opportunity for people in the organization that want to grow their careers to provide a mentorship opportunity, and for the new people to shadow them.

Both people are winning because the mentor wants to make sure the mentee is doing well, because it helps the company and they get a great feeling out of that, and it helps the mentee to get things much faster.

What are the shortcuts here to make it happen? Shadowing is important. Again, it creates opportunities for multiple people. I do believe in testing people in the message. You can make it fun. What I always like to say is “You’re going to bleed in here so you don’t sweat out there,” you’ve heard that a thousand times. What I mean by that is we’re going to be hard on the internal messaging as a team, and hard on each other to make sure we nail that so when you’re talking to a customer, it’s like “This is easy. That’s your objection? I got this.” It helps raise the bar for everybody.

Brent: That was an evolution. Once we had product marketing we had more sales people. With the first sales hire it’s going to be more of the shadowing and sitting with the founding team. Over time, yes, you can go build out those messaging, that curriculum, to go solve for that but that’s typically when it’s been designed by product marketers, sales, and a plethora of other people.

Trenton: When do you think that reps can accurately forecast their next quarter?

Brent: Never. Forecast is an interesting thing and once again this comes down to what your average deal cycle is. If your average deal cycle is 25 days and you’re signing people up and it’s predominantly inbound, there is no concept of a rep forecasting the next quarter. There’s going to be bigger deals out there. You’re going to be forecasting based on historical data. If I get a thousand leads, we convert at 32%, if you tweak my inbound leads to 1,500 this is my forecast. You forecast at a organizational level.

If you’re doing enterprise level deals and they’re going to have those longer sales cycles as they’re going into the next quarter, 50-60 days, then you can start saying “I have this many deals in stage one and this many deals in stage two,” and you can build that funnel out. But so many of those SaaS businesses right now are closed in an open and closed in month. Those things need to be derived from an organic perspective. It’s going to be a combination of your average deal size as well as some of the organic traffic, or looking at their funnel.

Trenton: A forecast for sales rep is their word, that is their handshake that they’re going to go execute X, and the best sales people take that as it’s serious. I believe a forecast is not one person doesn’t necessarily own that, it’s a team effort, especially when you’re higher in the organization. There should be multiple layers of scrubbing that forecast, and our forecast brings a great opportunity to teach individuals where they are and where they’re not in an account. To coach and mentor them to become sharper on their business, and I like forecast calls, I know you’ve been in a lot of them.

Brent: My point there is that forecast with a rep is derived in a way of helping them move a deal forward. It’s not necessarily coming up with the number of, “I’m going to go close $50K,” or whatever it might be. There is some of that, but I always use the forecast calls as an effort for me to understand their deals and their business better. Ultimately I take that understanding and plug it into the larger ecosystem trials, and the MQL count, the concept of organic growth. Then you come back and say “Here’s the numbers that we can go do as a business.”

Evaluating Sales Hires

Trenton: Some sales leaders, they go about their forecast calls in, I’ll say, a different way than I do.

I’m trying to understand the business and understand where the business as a whole is weak. If a number of people are held up on one stage, I try to look in the mirror.

Is that our job as leaders, that we’re not giving the team what they need? We’re not removing the blockers to help them move the deals through fast enough? The forecast calls are a great way to understand the overall health of your onboarding, health of your business, regardless of the number. In addition to the number.

When do you know if it’s working out or not? We’ve had this rep, it is month four and they are not making their number. Share with us some of the telltale signs are that someone is not going to make it. Right? They’re not working out.

Brent: There’s the concept of everyone looks at quota and everyone talks about revenue, and they go “The person didn’t hit the revenue number, they’re out.” That is fine. That’s one way to manage things. I do look at who owns that person’s success in the first three or four months, did you give them everything that you needed to give them to be successful? Was your revenue number bullshit? Did you make this up as a, “We think they can do a million dollars,” they did $50K, and whose fault is that? Was that a misalignment?

I typically break that down into the other things that they’re doing. Are they coming in, spending the time in the office to go do the activities that need to be getting done? Are they changing behaviors that aren’t working? We sit and do one on ones with our team and you give them an aspect of, an example is we have these types of leads coming in. My expectation is for you to go do these five things. Are they doing those five things? Are they taking that direction, internalizing that, and going forward and making those changes? Those are the small things you look into to say they’re not salvageable. If they are doing all those things, coming and putting in the effort, asking the right questions and making that effort. Sure.

There’s times where maybe the technology and the personality maybe doesn’t align to the buyer, and the person doesn’t necessarily align. But those are the people that I try to reinvest in.

They’re the ones that you want to go make work because they’re doing all the other things that you can’t coach out of every single person. You can have a quick trigger and pull the rug out from those people, but those are typically the people I try to invest in versus the other ones which I might look at and say “You’re not making a change to your behavior, you aren’t doing the small things, you’re not controlling the controllables. ” Sure, even if you have the revenue number I still might look at you and say “That was a deal that was handed to you. You’re still not the right rep for this role.” That’s why it’s important to take revenue out as the only the only factor when making a decision of looking or firing a rep.

Trenton: Perfect example of this would be SDR, sales development representatives,
or it’s typically called BDR business development representatives, where they’re typically earlier in their career and picking up the phone all day long and looking for opportunities. To get to your quota, it’s formulaic.

If there are 19 selling days on the month, you chop off a day and a half, two days if you’re generous for internal meetings and whatnot, now you have 17 selling days of the month. How many phone calls do they have to make at a conversion rate of X to hit the number, it’s just formulaic. If the reps are not making those phone calls, that’s it. I’m looking at metrics now. If they’re not making phone calls, why aren’t they making the phone calls? Then you can start measuring, how long are the phone calls? Maybe it’s that they are on the phone too long. That’s training, we can teach them to get off the phone faster, or maybe their quota was a little high.

But if they’re not putting in the effort or not putting in the work, then you hear me talk about thirsty horses. You can lead a horse to water but you can’t make him drink. I’m looking for people that want to learn, want to be mentored and want to grow, and to put their head down and drink, and will work the program that we have in place because the program will work. We’re going to tweak some things, but it’s going to work for you.

Brent: Though at the early stages, when you might not have all those metrics and might not have those things. You’re still just looking for those things. What can a rep control?

A rep can control energy, a rep can control effort, a rep can control their willingness to learn, a rep can control their activities.

If they aren’t hitting those things, and the big thing is you have to be honest. If that’s your expectation, if your expectation is to make 50 phone calls or your expectation is to write a report at the end of each week of the types of calls that you had, and you don’t tell them that, then that’s on you. But if you’re telling them “This is my expectations,” you are giving them those expectations, they agree “OK I can hit those expectations.” Then if they’re not being occurred, and those are things where you have to come back and say “Why didn’t this happen?” You want to give them a chance to coach versus “You didn’t do this. Let’s move on.” But if those things become a pattern, of not doing those controllables, then I think yes you probably have the wrong hire.

Trenton: I’ve also seen repeatedly, especially as you’re growing the organization, that between 16 and 20% of your team is not going to work out. That’s for various reasons. A bad hire, they got through the process somehow, fine. People have life events that they need to exit. They might have another opportunity really quickly, and so you have to over hire a little bit for that stuff too, as part of your modeling. Are there other questions or any questions in the audience that Brent and I might be able to answer?


The Two Rep Rule

Brent: It’s the concept of no one should ever be the only person doing that job in a company, especially for sales. It’s super lonely, especially if you’re the first sales hire, or even as you continue to hire. It’s always important to hire in buddies if you can. If the budget allows it. The reason being they ramp together, they theoretically should be performing at a similar line graph, they should fall within one range of each other.

It gives you the ability to metric them, and on the flip side it gives them a partner in crime to onboard with. They can share the same horror stories, and it gives them the ability to build up a quick connection. Everyone always remembers their new hire buddy. I remember Brett, I remember Courtney at Salesforce. You just remember that new person that you latch onto when you get started.

Trenton: You do it for competition reasons too, but you also do it again, you’re right, to metric. You hire two people that you think are similar, let’s see how they’re going to perform against each other. Not like we’re going to throw them in a pit together, but it’s important. It’s important because again it starts giving you data in how people are ramping, questions they’re asking, how you can help them, etc. Good question.

Key Metrics for Startups

Trenton: First of all, as a CEO you’re never going to stop selling. Look at Benioff, he’s always selling. If I look at Joe Tucci who ran EMC at the time, I would be going to meetings with Joe or be sitting around the executive table at Chevron with fortune one, and I’m just sitting there, I don’t say a word. And Joe Tucci is talking about X Y or Z. In your mind, you are never going to stop selling. First of all.

Second of all, it’s important to focus on how people buy for one of three reasons. They buy to make money, they buy to save money, and they buy to protect themselves from some sort of risk. That risk is usually tied back to not making enough money or not saving enough money. The metrics and things you should be thinking about are when you’re speaking to clients or thinking about your go to market strategy is “How do I put money in this person’s pocket? I can save them $10 million dollars by X, or I can make them $10 million dollars by Y. But you’re going to have to give me $2 million of that to get it.”

Brent: Rule of thumb is always 5x value for the money you’re asking.


In your mind, why would this audience buy my solution to make money and save money, protect themselves from some risk. What are the answers to those?

That will start flowing up the metrics that you want to see. I can’t tell you how many times I see a deck from someone at Heavybit, and I just wait. I want to see the numbers in the deck. I did this yesterday for a company. They had a pitch today, I hope it went well. I said “I don’t see one, not one number on the slide other than the page number. That’s all I see.” “What do you mean, Trenton?” “There’s no, ‘I increased this by this percentage rate, decreased that by this percentage. I can reduce your time to market.’ If you’re going to release an app to market and it’s going to make a million dollars a month, and we get you to market three months faster. That’s three million dollars. I’m only asking for one hundred thousand dollars.” Does that resonate?

Brent: I also think the key is, you have done some deals yourself as the founder, just to recognize how you sold is not scalable. Weird packaging, friends and family, networks. Don’t be afraid when a salesperson comes in and says “Great. But maybe that’s not the best way to go do it.”

Just have an open mind about blowing up some of the things that you were doing to get your first customers, because the way you landed your first 10 customers is not going to be the way you land your next 90.

Trenton: Good point. Something else that’s interesting is pick your dirty dozen clients that you have. Just pick a dozen. Go back to them and ask them, “What value did you see or think you were going to see when you bought? And what have you actually seen now?” I promise you over those dozen there are going to be things you’re going to learn about the value of your solution that you didn’t even think about that you could put into your message. It will happen. It’ll be like those lightbulbs. “OK. That’s what.” Then you put that on the website and you go from there. Do it, you’ll be shocked.

You’ll learn a lot, it’ll be fun, and your customers want to hear from the CEO.

They don’t want to hear from us.

Impact of Technical Products on Sales Ramp

Brent: One, just in general, it’s overstated how technical a sales team needs to be. Especially if you have a solutions engineer. In general what you’re looking for is you’re looking for salespeople who know the sales aspects. Can they do discovery? Can they provide value? Can they go get coffee when the sales engineer is doing this thing? Those are the things that you’re looking for that you don’t know as a technical team. Ramping with the sales engineer, or ramping with the solutions engineer is a blessing for a lot of salespeople because those are typically what I call translators. People who can translate down the functionality, or why things were built in a certain way, to a value to a customer.

If you give salespeople those value stories “This thing does that,” or “This provides this value,” or “This takes away this pain.” That’s where salespeople thrive.

It’s making sure that they are in an aspect of disseminating that technical product or disseminating those feature sets into those value based stories, because from there that’s typically where they can start ramping very quickly on very technical products.

Trenton: A lot of what a salesperson does is navigate the organization to get to the right decision makers. And that’s a lot of what a salesperson does to find champions, groom champions, get to the economic buyer, be able to talk on value, that’s what the salesperson is doing. There is a difference on technical products and how you have to onboard. The sales models I built where it’s like sales rep and SE [sales engineer], you can make an argument that the ramp is actually faster because the sales engineer, they’re paired, and they can help the rep. They’re doing chalk talks together because they’re a team. They’re at the whiteboard together, learning, and they’re using real customer examples to walk through deals in the pipeline. Then the rep and the SE will walk out of a room and you’ll think they were in two different meetings, because “What did you hear?” “I heard this,” and the sales rep is like, “I heard that.” You’ve got to bring that information together.

Brent: Sales engineers should be in all the forecast calls. If they’re working up they should be providing that perspective. They should be sitting in there. They own that forecaste as well, and so they should be empowered to speak up and say “That’s not the deal that rep is describing.” They should own some of the relationships. You map the sales person maybe to the economic buyer, you map the sales engineer to maybe the technical buyer, you want to make sure you’re not doubling up on efforts and you both are interacting with the same person. You should separate, especially if you’re selling to bigger companies.

Balancing Sales & Technical Training

Brent: The key is when you start hiring the first sales people that you start hiring at a technical company can’t be early in their career in the sales aspect. That’s the thing that they need to know. One, you might be as a founder, you might not have that acumen to go give them the training. Then it’s not fair for them from a career perspective. I hate when startups hire SDRs or those types of people as their first sales people, because it’s not fair to those SDRs. They’re not going to get any sales training whatsoever.

Ultimately your customers aren’t going to get a good experience because you can’t equip them.

As you do those lean start ups you do have to make the investment in hiring someone potentially a bit more expensive, because you’re not equipped to go give them the sales training that they need and ultimately you don’t have a ramp at all set up to do any sales training. Sales training in general is an ongoing thing. Companies invest billions of dollars in getting people trained on whether it’s MEDDIC, Sandler, you name it. There’s whole businesses that evolve around that. You really need to go and say “Does this person have that aspect of their career locked down? Because all I can help you on is the technical training. I can ramp you on the product, I can’t help you with sales.”

Trenton: I’ll give you a real world example. At PagerDuty, because of the product that we had in the sales process we developed, and I’m talking early. We were five, six million dollars. We were able to take SDRs, and I’m thinking about Nick as an example. He was an SDR at Box. We hired him as an SMB rep and now he’s the number one or two at PagerDuty. It’s great to see his whole career take off, which has been– Nick if you’re out there watching, congrats. But I had a rule with the recruiters, and that was, “I cannot hire anybody that does not know Salesforce. I can’t teach you how to sell, how to do Salesforce, and how to sell the solution. We don’t have time for it. We just don’t have time.” I’m OK hiring someone that has a lot of hunger and a little bit younger. But I can’t teach you Salesforce. That’s a non-starter.

Outsourcing the Sales Process

Brent: I’ve seen it work in a certain size. It’s the same way I look at when you’re ready to onboard a channel, you’re ready to maybe potentially look at some outsourcing. But imagine the playbook that you need an internal person to internalize, the technology, the people, the whole culture. Because there’s an aspect of “Why you?” versus another competitor, and it doesn’t necessarily boil down to technology. Sometimes it’s just, “This is the fun company to do business with.” They represent culturally the way we want to go do it. We were doing a deal with Nike, they came down to visit our offices in Mexico. They went to us and went to Tata, Tata was bigger and cheaper, had more people, all these things. They walked into our office, they saw that we had a basketball court and a track, and they were like “You guys are the people that we want to work with. You encompass the culture that we are at Nike.” That was wildly important for us to go get a deal with them.

That’s the problem when you do an outsourced or when you do channel sales, you need to be able to enable that team to embody the culture of what you’re trying to do. Sure, you can teach them “Here’s your sales script, here’s your value prop.” But ultimately that’s the thing that, unless you have someone who specifically spending time working with them, sitting with them, making sure that they enable that. That’s the miss. I see it miss on channel sales, I see it miss with outsourced teams. It’s that lack of– By the time they pass it over to you, their experience with them versus now their experience with you are so different it almost feels like you’re talking to two different companies.

Trenton: Institutional learning, and I can’t stress out enough, that your reps are talking to these people and they’re learning about what our product does not do that we need to fix. That we need to go, bug fix, build, whatever you want to call it.

The company needs that knowledge and needs that instant transformation, and you need people that are emotionally connected to what’s wrong with the product with people that are building the product.

They need to hear that and they need to feel the pain of it, need to understand it, and if you’re dialing it in “I’m not going to sell that today. They’ll have what they need,” you’re not going to have that emotional commitment. Because what we’re all looking for when we’re building these companies is emotional commitment from our teams. When you have emotional commitment in what you’re building, hold on, because it’s going to be really fun to watch what happens.

Brent: But I wouldn’t do it for anything more than potentially lead gen. You’ve got to make sure that you’re equipping them so that the deals that they pass to you are aligned to that experience.

Landing Customers

Brent: To get your first ten customers you do it any way you possibly can. You call friends, family. You got to tap that network because selling to the enterprise, people tend to be risk adverse. Signing on to a company where they don’t have any proof points is difficult. Going into any large organization, they latch on to proof points, references, they need those things. You’ll get caught up in procurement, you’ll get caught up in all these different areas because there’s multiple steps.

Ultimately the ways I’ve seen that when you have to go into an enterprise it’s typically done through the network, to be honest with you, to go get those first few customers into the enterprise segment. Otherwise you go build those proof points out with companies who don’t need them, and you have to go down market. But at least from my perspective we’ve always gone after people’s networks first, to get into our first few enterprise companies without those mid-market SMB proof points.

Trenton: Look, I don’t know about your technology. If it’s trial basis, if it’s land and expand. B
ut I’d say welcome to the big leagues. This is what you want to go do. You want to go start a company, you want to sell to enterprise, this is what you go do. And you go do it. This is where you start laser focusing your time on what you’re going to invest in, and what you’re not going to invest in. I wish there was a shortcut to it. I really do. I wish I could tell you a magic thing, but selling to enterprise is tough.

Network Sales Vs. Enterprise Deals

Trenton: You need revenue. That’s what you need.

You need to show your investors that there are people out there that will part with their money to invest in your technology.

Why do they part with their money to invest in your technology? Because they see value in it. Because they’re making money, saving money, protecting themselves from some sort of risk. That’s what you need, and that’s your job. A lot of companies started SMB, small medium business, because it’s a little bit faster and less hair on it than enterprise. But then you see New Relic. They went SMB, and they’re trying to go north to enterprise and AppDynamics went north to enterprise and they got bought by Cisco for a lot of money. They’re trying to go south down to SMB. You see this time and time again of companies going enterprise versus SMB. You need to go get revenue. That’s what you need to go do.

Brent: The concept of how much something should be sold for doesn’t exist for the first ten customers. It’s “Let’s come work out a deal.” I don’t think necessarily you want to say, “This is brand new,” but I do think you need to be honest “I’m in deal making mode,” because there’s a ton of value outside of the revenue in just seeing what their use cases are and understanding the value that they’re going to get from it.

Understanding Use Cases

Brent: You can sell to one side of the technology, but there’s the concept of also selling to directors and lower level people even at the enterprise. You can win quick deals with people who don’t necessarily represent massive amounts of budget, but do have a nice logo behind them. Once again, you’re going to still run into some issues potentially around “I need to see proof points,” but you can sell to individual directors as well, to go build that out from a ground swell perspective. You might not get revenue from the first two guys, or you might not get very much, but you might get enough use case to go get revenue from that account in the long term.

Recommended Sales Tools

Brent: The one thing about Salesforce is a good rep will require you to have it, because that’s what they’re used to. It’s a matter of “Yes, you can start with smaller tools,” there’s a Google one now.

Trenton: Google Doc?

Brent: I can’t remember, I think they rebranded. They’re Copper now. Copper, yeah. There’s things like that are growing, and Salesforce is what Oracle was when Salesforce was Copper in a lot of ways. It’s become its own thing. But ultimately it’s a solution that’s scalable, so if you have aspirations to be one hundred people it’s better to bite the bullet today than try to do a massive transition when it’s maybe a little too late. But there’s cheap plans on Salesforce as well too, that are only a couple hundred bucks. So you don’t have to start with their enterprise package, you can start with something smaller. Gong is good for recording calls. Zoom is pretty good, but honestly I got by with Google Hangouts for years. You don’t necessarily have to invest in that.

Trenton: What do you use to track all the emails?

Brent: There’s Yesware, there is Outreach, there’s a pretty good one that’s called Groove. That’s pretty price conscious as well, and they’re hungry to go win deals. They are a younger company. We used them at Wizeline, pretty good. But that does all the email flows and tracking, not ready for Marketo, but rep managed e-mail flows as well.

Trenton: That way it helps you. It templatizes your email, so you can be faster and you can test your message. Those two things.

Human Reps Vs. Chat Bots

Trenton: We are chat bots.

Brent: I do think parts of your job will be automated in the future, yes. TYou’re already seeing it. Logging phone calls, keeping your Rolodex. There’s things that have been automated for years. I don’t necessarily think that the concept of sales goes away. There’s too much value in a person trusting a person. People overestimate that people buy technology or people buy for other reasons, you buy from people and you buy from the trust that you have in that person. No, I don’t think it ever goes away, but I do think a lot of the remedial tasks that salespeople get bogged down on, get automated. Whether that’s sending follow up e-mails or doing a lot of those things, and you’ll move into more high value activities.

Trenton: There’s a lot of technology out there right now. A lot. There’s a number of companies that are doing testing on AI for SERs and e-mails, and it’s fascinating stuff. Understanding what questions they’re asking about the language and words they’re using, and how you should respond. That’s going to be phenomenal. If my kids were going to go into sales, which would be great if they did and they went down that road, there will be so many more solutions for them.

What you’ll find is, you’ll find the tools will get better and better and better, of having a sales rep interface when the count right when they’re ready to buy or when they’re ready to make a decision. That’s what’s going to happen. Because right now, we’re out there building compelling events and talking to people and, “We’re so great. This is why you need us.” We’re trying to drive those together. What will happen is sales will get involved when they’re closer and closer. Which is great. That’s what you want us to go do. I’m happy to go– I don’t want to say “Take orders,” but I’m happy to take it those last five yards.