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OCT 20, 2021 - 51 MIN

Defining the CRO with Intercom and Replicated

  • General Management
  • Sales

In this Speaker Series fireside, Intercom CRO Leandra Fishman and Replicated CRO Dustin Dean offer an insider's look at what it takes to be a successful CRO.


Developer startup founders making a move up-market into the enterprise face an all-new set of business challenges that require them to bolster or reshape their leadership teams. Among the most important of these enterprise focused leadership roles, particularly along the path to IPO, is that of the Chief Revenue Officer, or CRO.

In this Speaker Series fireside, Intercom CRO Leandra Fishman and Replicated CRO Dustin Dean offer an insider's look at what it takes to be a successful CRO.

Dustin: Leandra, if you could introduce yourself to the team, a bit about your role, and then I'll do the same.

Leandra: That sounds perfect. My name's Leandra Fishman, nice to meet everybody. I am CRO at Intercom. Recently, I came from SendGrid email infrastructure, and then Twilio through their acquisition.

And I've been in sales for, gosh, forever, my whole entire career. Hardware, software, and services, both on the consumer and enterprise. And I love solving customer problems and building teams. 

Dustin: Great, excellent. Quick background about myself. CRO at Replicated, I've been here about a year and a half. I've spent the bulk of my career at a company called LivePerson.

I began my time there in 2005 as a seller, worked my way up to be the EVP of a Global Sales Consulting Success role, which was fun. But I really enjoyed building companies, that's something that's more interesting to me.

So, happy to be here with y'all today. Also, I've been around for a bit of time. I've sold all the way back to CDs to put on servers, to today's containerization approach. I'm excited to be here with you all. I hope you find it valuable.

So first question. Can you just talk about the role you have at Intercom, the CRO role there, how you see it? And maybe more specifically, how you see it functioning at a developer infrastructure-focused startup level?

Defining the CRO

Leandra: Yeah, it's a great question. My role here at Intercom actually focuses on the whole entire customer journey. So really from start to finish, pre-sales, post-sales, customer success, support.

Because I think if you really focus on whatever your company's North Star is, that hopefully is generating the most revenue opportunity for the company, but at the lowest cost of sale.

And for me, it's really about the best customer experience and ensuring that customers gain the maximum value from your product or solution. So, as I know, the CRO role can vary across the organization, I think it really depends a lot on what that organization's revenue and customer acquisition model is.

And Dustin, I know you've been at several different companies and in a variety of different roles, how have you seen different configurations, especially as applied to developer infrastructure-type focus?

Dustin: Yeah, it's interesting, same scenario. My current role today, I look after sales, customer success, which for Replicated, involves both the pre-sales and the post-sales motions-- it's a pretty technical product that we sell-- marketing, and then RevOps, which I think we'll touch on a bit later in our conversation.

What I've found is that the role encompasses at a smaller company a bit more broadly across all those functions. And then as you mature as a company, I think specialization comes into play, senior leadership at different levels becomes more important at the C-team level.

So in terms of the teams that you currently oversee, could you clarify what those are again? You said from beginning to end, but which specific roles do you account for?

Leandra: I have the account executive teams, they're working on pre-sales. The BDRs and SDRs that are focusing on obviously, qualification. I have the relationship managers that are post-sales, along with the CSM team, that's really the technical arm of making sure that people have the opportunity to onboard and really get up on their architecture and their infrastructure well.

Also, having revenue operations, which you know is a critical piece. And I think that when you tie in support to it, it really adds a nice ability to look at that whole entire customer journey.

Because as you know, getting the customers is one thing, and keeping them is another, and the revenue and opportunity to expand to happy customers is really, really big. So I like to focus on both areas so I can make sure we're doing all the right things to get them in and the right things to keep them as well.

But I think it's interesting in a developer infrastructure company, sometimes a lot of the revenue can be very self-serve or developers are coming in through the website, it's not necessarily a sales-led motion.

Have you had experience on both sides where it's more self-serve driven or sales-driven?

Self-Serve vs. Sales

Dustin: No. Personally, I've not. Most of my career has been in more of the top-down motion that I think people talk about, traditional B2B selling. At Replicated, we've got some open source work that we do. Certainly, we've got an element that's built into the platform that we deliver.

Tell me more about that, because I'm actually curious to hear some of the differences that you see, and how have you seen those two motions play together?

Leandra: The CRO role is interesting because I think it's different in every company. Depending on the model and how you want to go-to-market, your needs can vary a lot depending on your customer experience.

And so, for me in the past, while I have never owned marketing or the self-serve revenue specifically, what I believe works best is when they work in harmony together.

So how can we plant a lot of seeds, bring customers on board, and then have the sales team then go in and be able to nurture and grow certain accounts depending on if those are more upmarket and larger accounts where there's the opportunity to expand or sell more products?

And so I find that bringing customers in at the lowest cost of sale and through the experience-- especially because developers, as you know, like to get their hands on the product, they want it to be simple and easy-- allowing the sales team and the technical teams to overlay to then help with that potential expansion and new product sales is a great opportunity to put those two pieces together.

Differences In the CRO Role

Dustin: You've been in the space for a long time, I'm sure a fairly extensive network. How does your role differ from your peers?

Leandra: The CRO can be really different at every company. For me, I keep the eye on total revenue, but I don't own all the channels that drive it. For example, I don't own marketing, which obviously owns community developer relationships, which owns the self-serve experience.

But I do own all of the other pieces and making sure that we're really connected in the pre-sales and the post-sales efforts. And again, the graduation from early stage to self-serve and then to expansion is really a critical, holistic way to approach things.

Do you own marketing in your CRO role?

Dustin: I do today. Although, again, bouncing around from a company size maturity perspective, I think it's something that I think a CRO can look after, as long as you're familiar with the functions and the motions that a marketing team needs to execute.

But in our case, Grant, our co-founder, and I decided that his product vision and his understanding of what they were trying to achieve when they set out, isn't something that I will ever actually be able to approximate.

So marketing from our perspective is more, looking after execution of day-to-day involvement, coordination amongst all the different functions, and then Grant providing a lot of direction and guidance and vision.

At some point, without a doubt, we'll have to get to a place where we'll hire a senior marketing leader that's got a lot more experience than I do, that's definitely not my superpower.

But I think that that's not uncommon, I think

smaller companies as you're just starting to get things moving along, there are a lot of basic blocking and tackling elements you can work on.

The first thing you need to do, I think, at an early stage startup is just get brand awareness. So that's one of the things that we face. I think we solve the problem that a lot of companies have, but just not aware that we exist.

So that's not a bad challenge to have. I'd actually prefer that challenge over many others, and establishing a digital presence and starting to get more of an outbound piece going.

Those are all fundamentals, and I think that if you've got exposure to that and you've seen it in the past, a CRO can look after that. But at some point, you need to really dive in and I think that bringing on somebody to the C team with that specific skillset and experience is pretty important.

Leandra: Yeah, absolutely. Do you have support in your organization? Because sometimes that's not common.

Dustin: That was the question. When you say support, technical support, like frontline, do you mean from an engineering perspective? Then I don't today, and again, we have a pretty technical product.

So we've had discussions internally recently about how we address the support function as again, we're at Series C so we've got more funding than we have people, and we're looking to expand our ability to support customers.

Interestingly enough, just last week, we were at an offsite, our first chance to get together. And as a group, we came together and thought, 'If we're going to address this, let's not necessarily look at traditional methods or models."

We're looking at support as an objective, not a function, which I think aligns pretty well with what you were saying:

focusing on the experience first, not focusing on who's going to fill the role and what organization it will fall under.

At LivePerson, there were two models. At one point, the support team reported into the CTO organization in Israel. At a later date though, we changed that and put leadership, at least of the support group while they were located overseas, into my stack and team.

We felt like it was really, really important because if you think about it, problems and all the decisions that are made from product development all the way through to sale and implementation, any and all issues roll downhill to support.

And having them have a voice and a seat at the table, we felt was pretty important because we were able to make decisions based on a set of maybe more comprehensive factors and inputs. So I worked in both ways.

Leandra: I like what you said about everyone's super power, because I think as you are building out your executive team, it's really important to understand what people's strengths and expertise are. And sometimes that's why I think configurations are different.

I think there are some sales leaders or CROs that wouldn't want to have support or are not that familiar, maybe with the mechanisms of how to run a good support organization, and the metrics, and the structure and things like that.

But I believe in the holistic approach, and there's just as much revenue, I think, in your existing customer base, as there can be in new. And so I love having the opportunity to have their impact all the way around.

Managing at Scale

Dustin: There's a question we hadn't talked about earlier, but I'm going to ask it anyway because I think it'll segue into one of the ones we discussed before.

The breadth of scope of a chief revenue officer, again, from the pre-sales all the way to maybe even marketing, demand gen, and all the way through to potentially support, what challenges have you experienced in your career in being able to manage just that breadth, irrespective of whether or not you've got experience in working with a support team or a customer success team?

Just managing the sheer scope at scale, I think is important because some people come in thinking, "I can do all of this." And then you get into it, and as an organization grows and becomes more complex, it's a bit more difficult to do that.

What experiences have you had?

Leandra: What's interesting is that I've had the great opportunity to work at a lot of different companies in a lot of different sizes and phases. And so I think sometimes you have a zone that you really know well, which could maybe be the growth stage, or the build stage, or the scale stage.

And so I think that when you can apply one, whatever your sweet spot is-- because while we can do a lot of things, I think everyone probably has maybe has a section of it that they love-- I think really understanding how to apply a playbook from what you've seen or what you've experienced will then allow the companies to really excel and grow faster.

And I think that sometimes that's what gets in the way of organizations scale, is that

they maybe have great people that haven't necessarily seen what those next layers look like.

And as you mentioned, the complexity of different models, whether it's direct or indirect, whether it's different channels or self-serve versus sales-led, all of the nuances that go in between, I think the best way that I've navigated through it is, I've had a lot of experience and dipped my tone in a lot of different things.

So I have a good understanding of how the general type of models work, but also I'm just an avid learner. And when I am in something, I immerse myself deep to understand the experience at every single layer.

And when I keep the customer in mind, it feels like it's the North Star that I need to figure that out and navigate through the complexities. I think priority is key, hiring the right people in the right places with the right experience, again, can really be the boost to growth that you need.

Dustin: So given the fact that the profile of an ideal CRO is of somebody that's fairly multidisciplinary and has had at least exposure, I think it's really important to be able to connect with the leadership team that you put together to solve problems. It's important to understand the mechanics behind every one of their day-to-day functions.

I was on a call with another investor that we have, a founder who's looking to hire a CRO, and the questions he was asking me were characteristics e.g. what do you look for? What do you think are most important?

If you could touch on it based on your experience, both early stage, mid stage, and then at a large scale, maybe starting with early stage. I think a lot of folks we have on the call today, maybe are having these same thoughts, "I'm ready. What should I look for?"

The Ideal CRO

Leandra: For early stage companies, I always really encourage the founder or the executive team to try and lay a little bit of the groundwork to understand, "Okay, what is our target customer profile? Where really do we have the best fit in terms of personas, or verticals, or industries?" And try and get a little bit of a ground swell where you can see, "Okay, we're starting to build something."

So you're hiring people ideally with some expertise, either in the model, again, sales-led or self-serve, or the expertise, if you're going more up-market and you're selling specifically into vertical solutions, you want to gain more knowledge into the leaders that you hire.

And you can do two things. You can either grow from within, which is nice because someone usually understands the technology, and the market, and customers and things like that. But the challenge with that is that then, they actually don't know what that next level looks like.

So they're not as equipped to know, "Okay, how do I scale? How do I go from one or two maybe account executives to a team of 10, or 20, or 50? And then how do I take it from a local perspective?" Whether that's either North America or going global.

Know, first of all, from a CEO's perspective, what are your strengths and your weaknesses? I think you mentioned, you've worked with leaders that have more of a passion for maybe different areas, and you've had to augment the other sides. I think there's very product-oriented CEOs and founders, there's marketing-oriented CEO/founders, there's even sales/customer-led CEO founders.

So add the layer of well rounded expertise to that, and then find somebody that's one step ahead of where you are

versus just hiring for exactly where you are, because they're going to be building the systems, the tools, the processes, because they know what it looks like when it gets bigger.

Dustin: Hire someone that understands what the house should look like and the fundamental pieces that need to be in a home-- there's got to be a few bedrooms, couple bathrooms, dining area, space to get around over here-- and understands the mechanics and what that should look like, but then is flexible enough to be able to build that house with a team and add rooms, and add furnishings, and the wiring, and everything else. 

Those are going to be different bespoke for every organization, but at least fundamentally understanding what does this organization look like in two years, three years time? And then how do we build towards that? I think that's super critical. That's advice I would give to anyone that's contemplating hiring someone in our function.

So to that end, thinking about how you build an organization, what are the most important functions that you think early stage companies should take a look at to start to compliment and fill in the CROs team overall?


Leandra: Yes. The most underrated position out there always, I know that you and I are in complete alignment on this, is revenue operations. They to me are like mission critical. I call them my glue sticks because without the glue, the whole thing's going to fall apart. And it's really important that you're setting it up for success in the beginning.

I'm sure you have seen like I have, you go into an organization 5 or 10 years in and you walk into just a CRM system or a lack thereof, or just all of these things where you have so much lifting to do, such a massive cleanup because there really wasn't strong revenue operations people in the beginning helping build that foundation. So you need to pour the foundation before you can even start furnishing the rooms.

I think that it's a team that gets underrated and undervalued, but the linchpin of having a great ability to scale quickly, is having the right infrastructure set up from an op side.

Dustin: Could not agree more. I've been fortunate enough to have the same RevOp leader with me for the last three roles I've had.

Leandra: Lucky for you. They're hard to find.

Dustin: Thank you, Greg. And it was one of the first hires I wanted to make for exactly that reason. The first thing that's important for folks that are building a company at scale to understand is, that there's a difference between that RevOps function and then the finance function, the more broader organizational operational function. 

Because in addition to being that connective tissue between different functions in my team and then even within finance or product or otherwise, that group is the single source of truth for me. I need to understand information data. I think you make data-driven decisions, I try to make data-different decisions too. And when you're early stage, you don't have access to that information.

And so without having someone in a position there to set up process systems and tools, it's really difficult to make decisions and plan to fill the room. You have to rely on gut feel and instinct.

I don't like being in that position, at least not 100%. I think the other thing that's interesting is that early stage, you've got an opportunity to create systems and implement tools and create a stack thoughtfully.

And if you ask any RevOps leader who's been in larger organizations and has had to deal with the cobbled together Frankensteinian CRM system with all the layered tools, giving them an opportunity to come in fresh to put together what they've learned and put it into application, you get a lot of excitement from folks in that role too.

So beyond the RevOps function, which again, I agree 100% is core, what else would you do? How would you prioritize the hiring of the balance of a team?

Leandra: Again, I think RevOps is critical, and obviously, it depends on what type of product you're selling and the need to really make sure on the technical side, you have the ability to hopefully differentiate a little bit between pre-sales and new customers, and then post-sales and current existing customers.

So looking at those two engines and making sure you're not asking everybody to do everything, that's one thing I think is challenging sometimes about a small startup."

Well, you're going to do the new business and the existing business, and, and, and." I find that most sales professionals are really better at one thing or one side of the fence than another.

And so I would really encourage people to look and make sure, while we all wear multiple hats in early stage startup, we're really focusing to understand where we can put the right expertise on the right side of the fence. And so you're not having everyone do everything because they just don't do it well. I'm sure you've seen that 100 times.

Dustin: For sure. Yeah, without a doubt. The early days here at Replicated, we had a pretty well thought out sales motion when I joined. So there had been a lot of work done for me, which was nice.

But structuring that, getting it set up was obviously the first piece. You have to get customers before you can then support them and make them successful. So that was the focus here.

And then it was interesting, I initially felt like we wouldn't necessarily need to add in a customer success component as soon as we did, but I very quickly realized that, as soon as we hired a leader in that function, you start knocking on customers doors who maybe you haven't spoken with as much as you would've just based on lack of resources.

And there's all sorts of things they have to say as you start to open the door, many of them positive, maybe many of them not quite as positive, which is fine. I've always felt like the next best thing or even better than a happy customer, is an unhappy one. So we had to accelerate that a bit and we were lucky enough to find some good people to step in there too. 

Time to Hire a CRO

What signals or inputs should founders look for to indicate that it's time to hire a chief revenue officer? Because you could hire a VP of Sales, you could hire the CRO, but at what point do you think folks should be speaking out, reaching out to their network, looking to their investors to start to think about putting this to plan together?

Leandra: I don't think people should hire a CRO too early. It might sound fun and look like, "Oh, I need somebody that's going to focus on all the revenue." But as I mentioned, I think different sales leaders have different expertise and I think the business evolves.

And so really thinking about, "Okay, how do I ensure that we've got the basics understanding of our sales motion going, we understand that go-to market strategy and we're seeing traction."

Because I think really with a CRO a lot of times is they're bringing the scale aspect as well as the revenue perspective across all the different channels. And as that's still developing, I think sometimes hiring a CRO too early is just not going to get the type of execution sometimes that's needed when you really need to have people closer to what's happening because they're going to be thinking a little bit more about strategy versus the tactical execution to some aspects.

And again, I think a CRO is more valuable when you're ready to scale versus when you're still building and growing, and it's not quite as clear. I think it's better to also allow that opportunity to bring in people as the stage grows.

Because if you hire someone at a CRO level, 1) they're usually not going to have expertise going from build, grow and scale. And so you're already topping out at whatever expertise that person has versus starting at the bottom and saying, "Okay, I'm first going to hire a Sales Director and then maybe a VP of Sales."

And then you're getting all the signals and the data points that you're ready then to be very, very clear when you're looking for your CRO, "Okay, this is our business model now that is defined. And I want to find somebody exactly with this expertise to pour on the gas," versus still building the engine and maybe not getting the right CRO.

Dustin: I couldn't agree more. Being open and candid about my own experiences, I came out of a long great relationship at LivePerson, wanted to get back to doing things that I love, which is building small to larger. And I learned a lot in the couple roles prior to my one at Replicated. And the key piece is product-market fit is critical.

One of the beautiful things that I saw when I talked to Greg about this opportunity was that the culmination of a couple major market factors had come together, they'd spent three or four years really iterating, understanding the product, more clearly defining the problem that they were solving.

And I think the trigger for Replicated was having those first one, two, three customers that were substantial, that embraced it, understood the value proposition. So the product-market fit piece is key, for sure.

What metrics do you look at, and how do you do that? And then how do you align teams to support the overall business? I think to preface that, my measurement is net ARR add every quarter. And there's a lot of levers that go into that from the new logo sales and new bookings to revenue retention and renewals and growth.

What metrics do you look for? And maybe, how does that evolve? You start with a simple set probably, and then over time, you start to build the ability to measure more things and gain more insights, but what's important to you?

Metrics and Alignment

Leandra: You've nailed it, Dustin, we're the same way. We're focusing on net ARR increase and obviously, the different teams are always looking for ways to tie into that.

And I think before you can start looking at metrics, you have to assume you've got some good systems and processes because it's an output from those types of things. And so knowing how to hire people and when, and what it should look like, you have to have those metrics.

I think the metrics tie in, as you mentioned, to each organization differently to that number, whether it's new logos, whether it's expansion, or churn, or contraction, or customer set, all of the different things can tie into what that total revenue number is, but there's also things that impacts the revenue number.

So a lot of people are just like, "Well, we're just focusing on the number." Well, are you maximizing your opportunity for that number? Pricing and packaging, for example, has been a huge thing that I focused on and you would think, "Oh, why are you focusing on pricing and packaging? Isn't that someone else's job?"

But that is a critical aspect, what goes into figuring out how we articulate our value, how we make sure in negotiations we're negotiating off the right set of inputs so we can articulate that back out through ROI calculators and things like that.

So while revenue is always at the tie, you have to look at what drives revenue and ensure that you've got metrics across the board that everyone can relate back to, but also that you've got the systems and the infrastructure to deliver the maximum of whatever that is. And sometimes it can be hidden like I said, in pricing and packaging.

Dustin: Without a doubt. I'm curious now, I'm going to ask you a selfish question. Do you see pricing and packaging as it relates to either the macros that you need to look at in order to drive pipeline and drive the growth relative to interaction with a CTO or a CPO?

Because I think we're finding that that's super important, collaborating, especially the packaging piece developments. Do you have experience doing that as well?

Leandra: Yeah. And it really depends on where you're focused in terms of your go-to market strategy. So the pricing and packaging that you might need could look very different in a self-serve credit card model than it would in an expansion enterprise type model.

I think that that's where you're really looking at your ASPs or your ACB, your annual contract value, or your average selling price, and you're saying, "Am I tying the ROI that customers are getting to the pricing that we're providing?"

And this is where customers can in a good way, get the benefit of very early stage pricing, where it actually doesn't take advantage of the scale opportunity that they have and they're just looking at some metric that's very, very small.

I think one of the best metrics that people can have in their pricing models is usage, because when you are riding usage, you're riding the wave.

When you are selling to individual people or you're selling some type of license that is just one, a lot of times you can't capture the value that we're providing to customers. And hopefully, whatever your cost is, the value that a customer is getting out, you can quantify, and that's a 7-10x value.

I've seen in some companies, you come in and you're charging $100,000, which seems huge to that startup company. But you know what the customer's getting five million worth of value out of it and you're like, "Oh my gosh, we should be charging $500,000 for them to get five million." And yet, the pricing and packaging doesn't match up in a way that everybody wins, the customer is just winning and the company isn't.

Dustin: Without a doubt. I think you're spot on with respect to the usage-based component. And I think that one of the things that I look for, and I think founders should be thinking about, is their demonstrable value propositions financial that's tied to the solution itself.

If a founder can envision that, it's maybe time to get a CRO on board, and then allow that person just play with that and flesh it out. But that is definitely the key.

I think that if you can tie a scalable value proposition that scales with the scale of your solution, it sounds obvious, but I think it's often overlooked, especially early stage. When you're looking and a deal looks great, it's important to set the precedent early on to tie value back.

Is there a metric that you could think about that maybe has the opposite effect and maybe has created conflict between teams?

Leandra: If I was to think about metrics, I think that they hurt when they're in silos and they're not really tied back to the one type of goal. For example, if a product team is really just focused on hitting launch dates, and they're going to unfortunately run into challenges and obstacles, they're going to start cutting corners.

And unfortunately, maybe they deliver a product that hasn't been really fully tested and has a lot of bugs in it. Well, the impact of that on customer satisfaction and customer trust, and maybe even churn is really big.

And so it's like, how can you take that approach to make sure whatever the goals are, that they are connected into one? Something as high level as a revenue target, might cause people to think like, "If I'm in product, why does that really impact me?"

But if you really look at how your job can tie into whatever that company North Star goal is, revenue or whatever that would be, you really allow people to align their behaviors, their intentions, their attitudes, and their efforts to that goal. 

Then you don't have people like, "Well, I don't really care about that. That's your problem. I'm going to work on this because I think that that's a benefit," when really it's not adding to the holistic good.

Dustin: My own observation on that-- and again we're in a real time position facing these challenges everyday-- I want top line revenue and top line pipeline, top of funnel pipeline to increase.

Obviously I would like that. And I think

a healthy pipeline is comprised of a lot of smaller opportunities that grow larger.

Some that'll stay where they are, midsize opportunities, and then you start to move up market signing higher ASP deals.

That said, with limited resources at a Series B/C startup, my decision to introduce a low price point option to entice more customers to join, has an extremely large impact on our support organization. That's why I asked earlier about that.

For me, aligning the functional metrics, marketing, sales, customer success, or retention, all of them, those are pretty easy to do, but making sure that you keep an eye on whatever decisions you're making and how that might impact the rest of the organization is pretty critical.

That's where I've seen metrics maybe driving functions and groups apart.

Leandra: No matter what your metrics are, when we're actually not transparent across the board and what everybody's driving to, that's when I think you do have people that are like, "Yeah, let's just sign up more customers. That's going to help me drive revenue." But then the ripple effect, as you mentioned, could actually be harder on the organization than what it's worth,

Aligning Product/Sales/Marketing

Dustin: Especially as you're scaling, I think that's the key, without a doubt. Another topic that's come up, in your experience, are there early product/sales/marketing decisions that can have an oversized or outsized impact, positive or negative as you start to grow?

Leandra: Yes. If there's one thing that I think is so important, it's having a really good system, ideally not excel, for opportunity in pipeline management.

So you can really have visibility, because what's interesting is-- I use the term random act of sales violence-- in an early-stage company, everybody's just trying to sell anything to anyone. And it's really hard to look for the patterns, the trends, to look in your pipeline and look at the stages to say, "Okay, what's working and not working."

We never feel like we have enough at the bottom. Is it that you're getting stuck in discovery and qualification because maybe you're not really understanding the customer pain, you're not being able to articulate challenges and value?

Or are you getting stuck in solution evaluation because maybe we're missing some critical product feature functionality that's really required? Or are you getting all the way to contract and you can't get things through because maybe you've got some legal terms? Or maybe your pricing and packaging is not really aligning to how the customers wants to buy.

So if you're not tracking those, you're not going to know where to fix it, and everyone just wants to throw their baby out with the bath water. This is the one thing I would encourage every founder to do: understand your win and your loss reasons.

So you can go back and either replicate what's working or why you're not winning, feeding that back into marketing, into product, into R&D, thinking about that in your strategy, saying, "Wow, we are really seeing now a consecutive pattern about a customer requirement, or a market situation, or a competitive landscape."

It's hard if you're not looking at the data to really make the right decisions if you don't have a good system that has good information going in so you can assess that. I'm sure you have seen this over and over again, Dustin, where you've tried to go to the data and the data's either not there or it's not clean.

Dustin: It's not there, it's not clean. Exactly. We will keep coming back to that, without a doubt. It's interesting though too, to be open enough and be creative enough, especially as you're developing that set of tools and processes to measure.

We have a lead-to-cash measurement system now, it's all in place. I can see top of funnel down the bottom, but it's not been long in place. And so as much as I would like to see top to bottom and then be able to make decisions on that, I think you have to be flexible enough to look at what we can measure and how we can measure progress in advancement or not. And in our case, it's looking at top of funnel opportunities that are created.

If I can't look at six, 12, 18 months data to make decisions all the way down, what I can do is take a look at of those opportunities, how many are progressing, in what way, what types of opportunities are progressing, more importantly, maybe which are not, and why are they not?

So taking the opportunity to at least measure advancement through a top to bottom funnel, I think is also something that's important to do. You don't have to wait.

Parting piece of advice to founders, CEOs, contemplating bringing a CRO on board, what's the single biggest takeaway you'd like people to take from today's discussion?

Leandra: There's so many decisions that CEO and founders need to make across so many different areas. I'd really be thoughtful about what is really a permanent, which I call like one-way door versus a two-way door, something that you can change? 

When I think of permanent one-way door, sometimes those can be things like pricing and packaging. You can edit and change them, but when you set up your billing system, for example, I don't know if we've ever been at a company that 10 years down the road is still on that same billing system, and then it prevents you from being able to you a lot of things, because you really locked yourself in.

So just thinking a little bit about, what are the really big decisions that I need to be really thoughtful for? And then how can I be thinking a little bit about flexibility in the future? And then what are the things that you can be fluid on? Whether that's your persona that you're deciding to go after, or whether it's different things that you want to try in terms of marketing campaigns and things like that.

That's easy to change, but I think things that either affect customers or affect employees on the same side, those can sometimes be a little bit stickier and you really want just to be thoughtful about approach.

What's your one thing, have you seen something that you've learned as one piece of advice that you would offer?

Dustin: Well, making the investment, and it is an investment for sure, in time and energy and in your company's development. It'll sound obvious, but I think it's over looked. Product market fit, make sure you've figured it out. What trends are behind you? What wind is behind your sails? Do you have some momentum? Is the product market fit there? Are you solving the problem the way you think?

And more importantly, are the customers perceiving value the way you intend? That's probably the most critical piece. So that's probably the single biggest pivot point where, yeah, time to bring somebody in who can take a look, decide what the house might look like and then help, go to work building it.

Leandra: Yeah. People are everything and time is a short resource that we always feel like we never have enough of, and so I think you're absolutely right.

Ted: That was great. Thank you so much.

Dustin: Folks have anything that they'd like to ask us?


Ted: Yeah. We got a couple questions. I just wanted say, this revenue operations role sounds like extremely important. It's just incredible. We'll get any open reqs that you maybe have at both of your teams to help fill some of those roles.

But I guess to that point, we didn't really talk about tools, a lot of more strategy and process. Is there a perfect operations tool for this revenue work? I'd love to just hear a little bit about how both of you run that at your companies.

Leandra: Ted, that could be a new startup for you, a new idea, the perfect operations tool. I don't think there is one perfect tool out there. And as you know, there's many companies that are coming to market with something better than what they have.

I think

what's more important is the connection of the tools together and the clarity of the process, so everybody's marching in the same direction, because the best tool doesn't mean anything if nobody uses it.

So it's what tool works for you at the stage that you're at and making sure that people are really adopting it and your team's able to use, and everybody understands the data and information that's coming in and out of it. Dustin, do you know of a perfect tool you can use?

Dustin: If somebody comes to me with that, I'll invest, I'd be happy to. No, I think it's important, and you touched on it, I think the use of the tools is undervalued.

People look at it and they think, "Okay, we need a CRM system and a marketing automation solution, measurement tool here. And I'd like to have a forecasting to a rate over my CRM piece. And we need something to manage retention." That's all critical.

We decided to empower our RevOp team to hire folks that can specialize in each one of those functions. So my customer success team has a proxy and a representative on the RevOps group, and the marketing team has one, the sales team has one.

All of that's really good, but if you don't do a good job of making sure people in the organization understand both the value and how they should be utilizing it, nothing will work. It just won't work.

So the stack is important, the processes are important, the usage, and I think making sure you give your internal stakeholders a point of view on the value that they're going to see from that is important.

Too often I think people at the leadership level, look at those systems and tools and think about, "Well, what am I getting out of it?" And to get something out of it, you need to make sure people are participating with it. And to do that, I think you need to demonstrate value back to the individual folks that are working with you.

SalesOps vs RevOps

Ted: So it sounds like there's an element of letting people use the tool that they want and then have excellent operations people that can use APIs to bring all those things together. It's something we see in the technical side of the house as well.

Leandra, you did call out this, how do you differentiate sales operations from revenue operations? Or are they the exact the same?

Leandra: It's such a great question because I'm seeing it evolve. I'd be curious to know what you think about this, Dustin, but it used to be sales operations was in the sales island, marketing operations is on the marketing island, and finance operations is on the finance island. Everybody was their own island, and you really didn't have the synergies in all of the things, tools, metrics, analysis, understanding.

And what's happening is revenue operations is like this new thing almost. Over the last couple years, it is coming together where it's like all of the things live in one operations place. And so it's really like a connection of the tools, the systems, the information, and looking it from an end to end.

When I got to Intercom, I said, "Let's stop having go-to market meetings where it's like, here's a sales update, and the marketing update, and the finance update, whatever. Let's look at the funnel."

And we all own different parts of that funnel, but let's all feel connected to it knowing that every single aspect, whether it's top of funnel which is marketing, or whether it's middle of funnel which is maybe more sales, or the bottom of the funnel, especially as we're looking at churn and things like that, is support and things like that.

Let's look at that end to end and know where the accountability and the ownership lies, but let's not separate all the pieces, let's have the synergy and the cohesiveness of having one operations team. Dustin, do you have a revenue operations team or is everything separate?

Dustin: I do. We have revenue operations with a leader, and again, we have a sales op function under that, there's a customer success op function, marketing ops, enablement falls underneath that as well.

Everything that touches the overall group, because I think that to take what you were saying maybe one step further, just to articulate it in my thinking, if I'm managing net ARR add, and that's what I'm responsible for, that is not just sales, that's retention, that's renewals, that's marketing, that's all of that.

And if I can't get visibility top to bottom and from left to right to that whole piece, I can't make decisions that are thoughtful bearing all those factors in mind.

So sales op is super critical, but making sure that I understand the implication of our pricing and packaging and how that might be affecting the downstream impacts because we created a model where customers are growing faster than CS organization can keep up, that's important.

And if I'm looking at it in silos, I have to piece those things together in my own head. And I don't frankly have the capacity to do that, I'm not smart enough. So sales ops is a key component, the revenue ops in my mind, brings it all together and allows you to make decisions based on all those different levers and how they play together.

Enterprise GTM

Ted: We have one other question in the Q&A tool. This is around moving up-market to enterprise go-to market.

So this is generally like dev-first, bottom-up, and now you add on the enterprise motion, what do you think a successful CRO needs from their marketing teams? And so if you're a CRO who owns marketing, what does that relationship look like? And if there's a CMO that you interface with, what are the main collective goals there?

Dustin: Early stage, if you haven't moved upstream into that true top-down motion, you're going to be focused a lot more on brand awareness and trying to make sure people are knowledgeable and understand your value proposition so that they have that.

If they have the problem that you solve, they're coming to your website, they're taking care of those things, and that's an important piece of market. You have to start to get a little bit more tailored in terms of how you're reaching, who you're reaching out to and how you're reaching them.

And so account based marketing comes into play, and enlisting good cooperation and collaboration between marketing, like an outbound demand gen team who's now reaching out with buyer personas and messaging and things like that that they're trying to work on.

And then incorporating the sales function. I'm a pretty big believer, anybody that's ever worked with me will know that salespeople should own their own funnel, especially in that top-down motion. So giving them support, but doing it in such a way that'll enable them to start to create better tighter ties when they're doing their outbound prospecting is key.

Leandra: Yeah. I call the difference between net fishing and spear fishing where your marketing is casting a big net and they're going to collect all the fish and hopefully they're in the right areas and you're distributing in a way where everyone gets to eat, and sales is doing a little bit more spear fishing.

I think, especially as you go up-market for enterprise, there's smaller and smaller of the thousands of companies, obviously that are an enterprise, you have to really be targeted.

And I think you need a whole different set of marketing strategies for that. It's much more around analysts, it's much more around the PR, going at the problems.

And a lot times it's more custom, as you said, either tailored to that C-level persona. And you're talking much more about value and problems and benefits and change versus just the feature functionality.

So you move, from small business or developers-- where they're flexible, they love change, they want to do it themselves, they're easy to go, they're curious-- to the more mid-market-- where they really want to see what everybody's else is doing-- to enterprise-- where it's like, "We've already been burned and you got to really prove it to us."

There's not a lot of progressive change in agents and enough places in enterprise that are constantly like, "Yeah, let's rip and replace this whole thing," because they have all this legacy.

So you have to do a whole different sales motion. You need your marketing team really focused on the ROI sell, you need them focused on the awareness, because those enterprise leaders are going to have other experts.

If you're not even on those type of radars, you're not going to be in the sphere of recommendations because at that level, they're probably doing RFPs and they're just going out to the top vendors, and they've already decided sometimes before you even have a chance to introduce yourself whether they think you're a viable option or not.

So I think a lot of it is, you mentioned the brand awareness, the messaging, but I think also the reach. And people that are hopefully talking about your product for you and having case studies, customer references, that makes a huge difference at all of the different segments. So making sure your marketing team is really building the story and the evidence to support that.

Dustin: I'll make one final comment on that. I think that if you're making that move or are in the midst of making that move, one of the nice things about being in a position where we are-- we don't know what we don't know in a lot of cases yet. And that's fun, that's interesting, but you learn more and more about your customers.

And as you get dialed in on personas and what value you're delivering and how they perceive it, you can start making that movement to a more tailored approach to marketing.

But you can also use that wide net to inform future decisions, because you start to see who buys your product. And, "Interesting, that vertical seems interested in what we do. Great. We didn't focus on that prior, but let's take what we've learned and inform our enterprise motion up." So they can work in concert, they definitely don't need to be treated separately.

Leandra: Absolutely. I call my CMO my bestie. If the sales and the marketing teams are not working as one, you're just not going to be able to go to the potential MSP that you want to. When everybody focuses on the customer, everybody wins, including the customer.

Dustin: Agreed.

Ted: Yeah. Those are the two main takeaways, focusing on the customer is your North Star, and have an excellent operations team to keep everything moving to win their attention.

Dustin: I'm going to have to give my entire team a raise, I think, after this.

Leandra: You might not thank us now, but you'll thank us later, just trust us on that one.

Dustin: Exactly.

Ted: I think that that's all the questions. I just want to thank you both so much for your time today. This is just an exceptional talk.

Dustin: Leandra, great working with you.

Leandra: It was a pleasure chatting, Dustin. And Ted, thanks for pulling us all together.