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GTM Navigator is our ongoing series where we break down the essential components of nailing the right go-to-market strategy. 

In this episode, Nick Daley, Senior Associate at Fin Capital, speaks to Bryan Caplin, CRO at Newsela and Advisor at Thoropass. Bryan has 20+ years of international success through leading, scaling, and developing high-performing revenue organizations within both venture-backed growth companies and publicly traded organizations.  

We hope in this edition you’ll gain insights into how to build and scale a RevOps team, the role RevOps plays as a company matures, and useful KPIs & data points used within the role of RevOps.  

Key Questions Discussed: 

Transcription (edited for clarity): 

Nick Daley (00:06): Bryan, welcome to Fin Capital’s GTM Navigator. It’s great to have you on today to talk about one of the most requested topics from our early-stage portfolio. I think to start off, especially for a lot of our early-stage founders joining the call who might be a bit less familiar with RevOps, would be really curious to know, how do you define the RevOps function? 

Bryan Caplin (01:14): For me, a high performing RevOps team should be my eyes and ears of what’s actually happening in the business day to day, right? As a CRO, you’re likely across many different functions, new business marketing, renewals, expansion partnerships, and it can be hard to really stay focused on the underlying mechanics of the business – what’s going well, what’s not going well, trends that we’re seeing, etc. To me, a RevOps function is beyond the very tactical things that they do from putting in place your tech stack and ensuring your deals are progressing from a Salesforce perspective and salespeople are getting paid on time, all of the very tactical things which we can talk about for me, they’re providing hopefully insights into what’s actually happening in the business. They’re spotting things before I am or even my leaders are, and bringing them to our attention, whether that be pipeline trends or closed won and closed loss trends or renewal trends – they are bringing those actionable insights that hopefully inform your sales and go-to-market strategy. 

Nick Daley (02:34): That’s really helpful. I’m curious, what business KPIs do those insights typically tie to? You mentioned a few different strands there across current contracts and then even going as far as pipeline, what are the key KPIs? What do you typically tie the results of the RevOps function too? 

Bryan Caplin (04:31): Well, really every element of your sales funnel for sure. I lean on them to help me understand what’s happening in our top of funnel lead generation. What are our stats on from an outbound perspective, whether that’s email, open rate and engagement rate, or connections on the phone. Are we being efficient and effective from a top of funnel perspective? Going further down the funnel, they’re helping me understand where are we having success on or not having success with from a funnel progression perspective. Where are our deals getting stalled? Are there any trends there by account executive or customer size or location or industry? And then when we get down to the bottom of the funnel, when we win, why are we winning when we lose, why are we losing? What are the pricing trends that we’re seeing there? There’s a whole set of KPIs and metrics that’re helping me keep my eyes on from a new business perspective, from an existing business side, somewhat similar. 

What’s happening from a renewal rate perspective, from an expansion opportunity (when we are expanding), what’s true about those organizations and how should we shift our focus there? Certainly, looking at NDR and GDR, is our book of business growing over time, and if so, how and where? Helping us make smarter decisions on the customers we spend our time with and those that maybe we spend less time with and then pulling back. They’re helping with territory strategy and design with comp plan, territory comp plan, strategy and design, book of business segmentation. Really putting the infrastructure and helping with org design to further enable us to hit whatever targets we’re trying to hit. 

Nick Daley (04:46): Yeah, I love the way you put that – of building this infrastructure to connect the different teams. I’ve worked at a handful of B2B SaaS companies and things of that nature and that disconnect typically between sales, customer success, all with different KPIs, and I feel like there’s always a struggle of all of them to align into one vision, but also sharing insights between them that benefit each other and that seems to be a key part of the infrastructure here. 

Bryan Caplin (005:12): Absolutely. Couldn’t agree more. 

Nick Daley (05:17): How does this differ to people who might be joining the call and thinking, “oh, it sounds quite like sales ops as well” – Is that part of RevOps or is it a different category to you? 

Bryan Caplin (05:27): I think ops was how this function started. It was very much focused on new business, supporting the sales organization, and helping them become more effective and understand what’s working, what’s not. I think over time CROs and CFOs have realized, well, you can also apply a lot of their same methodologies and tools to the other parts of the go-to-market organization, whether that be the customer side of the house or marketing partnerships, et cetera. RevOps is a more all-encompassing function and description that supports not just the new business organization, but the complete bow tie or funnel or however you want to think about your go-to-market function. 

Nick Daley (06:26): Awesome. That’s really helpful. As you know at Fin, we work with teams as early as pre-seed with maybe founder led sales, the dominant approach, and then all the way through IPO where those teams are typically very built out, very structured sales and adjacent teams. From your experience, at what point in that continuum do you think is the right time for founders and operators to think about building out a RevOps function? 

Bryan Caplin (06:50): I am a fan of building it out as soon as possible. I think some folks will wait until they have a certain number of salespeople or a certain number of customer success folks, but to me, that level of insight that they’re bringing the earlier, the better. You want to be correcting on your go-to market strategy, especially as you’re trying to figure out where you have product market fit or you don’t. I think having someone who can be those eyes and ears while your early sales folks or early customer success folks, whoever it might be, are focused on the bringing in new prospects. Having someone that can be, “Hey, I think we should be running more tests here”, or “This isn’t working”, the sooner the better, and it’s one of those, you get a lot of scale out of this role, you get an impact that has felt pretty wide across the organization. I’m a fan of hiring this person in parallel with your first AE or certainly your first sales leader. They will have an impact even if you don’t have a team of 30 reps. 

Nick Daley (07:55): Absolutely. I mean, as you kind of said earlier, it seems more like a kind of thought process, like a framework that can be started really from day one, and then obviously getting that structure in place as early as possible is going to make sure that everyone’s aligning on day one on where they’re starting, instead of having to bring together those maybe slightly different teams later on in the process and trying to drag them back into a central path. 

Bryan Caplin (08:18): You often see, I can’t think of every company I’ve been at, there’s always the, “oh yeah, this was back before we had this in place or this person in here or this process in place”. It was the wild west, this and that. There’s a lot to get done right from the start, have someone who knows what they’re doing in terms of setting up your CRM instance, whoever you’re going to use, setting up your marketing automation platform correctly. Get an expert who’s done it before, I think we’ll see a lot less pain and heartache and rework down the line. 

Nick Daley (08:49): Yeah, absolutely. I would love to touch on some of the more practical pieces of advice getting set up from day one a bit later, but maybe as we continue talking about that continuum between early stage all the way through, what role does RevOps play as the company matures and how do you adapt that strategy during different phases of growth? 

Bryan Caplin (09:13): As a company matures I think the function or the impact that RevOps has, I don’t think changes materially, but I think you’re able to now build in specialization as you grow. You can start to say, okay, within my RevOps organization, I’m going to have a marketing ops specialist or someone focused on the customer side of the house or someone focused on new business side, or a tech expert who’s going to really own the tech stack and whatever Salesforce or CRM changes we want to make, or marketing automation changes we want to make. I think the scope and mandate of the organization doesn’t necessarily change as you grow and scale, but I think what it allows you to do is specialize a bit more. So you have people that are laser focused on your new business funnel or your customer success process or whatever it might be. 

Nick Daley (10:10): So it’s really at that stage about scaling the infrastructure, being able to divide the RevOps into separate, different layers of insight, whether that’s on the marketing pipeline side and then letting a sub-function leader run with that it seems? 

Bryan Caplin (10:25): Yep, exactly. 

Nick Daley (10:27): I think a lot of people will be thinking, what are the key metrics that you use to measure success of that team, and how do you track improvements quarter over quarter or year over year? 

Bryan Caplin (10:40): Yeah, it is tricky, because they are not directly impacting pipeline generation or win rates, but you can do things around Salesforce CRM hygiene or whatever it might be, but what I tend to like to do is pick a KPI or two to focus on for a six-month process. For example, maybe we’re trying to improve our win rate by x percent, or our renewal rate, or our discount rate, and things where I do think that the RevOps function is shining a bright light on something we’re doing well or not doing well. It’s driving adherence to a process or a system that can impact that KPI. That’s where I’ve seen some success before in the past. It is a tricky balance because again, they’re not directly impacting close/won business or renewals. Everyone in my revenue org always is gold on our top line goals, so I want everyone to have some skin in the game. Whether that is the quarterly new business number, or the quarterly renewal number, or expansion, or whatever it might be, they certainly always have that part of their variable. I want everyone to have some skin in the game on our overall success as a business. 

Nick Daley (12:11): Interesting. What I get sense of there is obviously, one is enhancing focus and these sprints. Then secondly, is making sure that everyone’s aligned. I think the third piece I’d be curious to get your sense of is incentivization and compensation. How do you look at that as a RevOps team member when they don’t have direct applicability to typical sales KPIs as such? 

Bryan Caplin (12:34): Yeah, you got to be careful, right? You don’t want to incentivize them on things that maybe cause them to make different decisions or look for trends that are in support of them making more money in their variable comp plan, right? If it’s heavily focused on new business, they may make some recommendations or be looking for some signals that are not real but are in support of generating more new business at the expense of margin, for example. It tends to be a role where it’s more heavily base comp structured versus variable, but again, I do want them to have some skin in the game so that when the company does well or the revenue work does well, they are reaping those rewards. They clearly have been a part of that. And when we’re struggling a little bit, I want them to be a part of the feel like we’re one team and they’re working to get the ship righted. It tends to be like an 80 20 kind of base to variable mix, maybe even 90 10 depending on the level and role and size and stage, but again, certainly want them to have some skin in the game for overall performance of the revenue work. 

Nick Daley (13:50): Absolutely. It seems like a very delicate balance and I’m sure every company in each stage is kind of different and matures as the company grows. Maybe we could change tracks a little bit. I’d love to jump into some practical advice you have for founders and operators listening here – to any founder/operator starting to build out their RevOps function today, what do you think are the necessary two or three ingredients for excellence? 

Bryan Caplin (14:21): Well, the first hire in, I think you need someone who is clearly a self-starter and can operate with minimal direction. This can be tricky. You probably can’t afford a seasoned leader who’s done this for 15 or 20 years, but you want someone that has seen what good looks like. I’ve tended to look for people that have come from larger ops organizations where they’ve worked with excellent leaders or first line managers, and have seen what good looks like and can take that and bring it to your organization, but they have that independence and initiative and a real self-starter to kind of do things independently and on their own. Ideally someone that you can grow with for a couple of years, though doesn’t necessarily have to be the future head of a large function, that would probably be a unicorn. Maybe you get lucky, but certainly someone that can grow with you for a couple years and hopefully stay on when you bring on a more experienced leader. 

If not, that’s okay too. But someone that has the ability to get stuff done without being told what to do day in and day out, I think you need someone that’s incredibly collaborative. This is one of the more cross-functional roles in any organization. Their constituents are sales, marketing, customer success, and the finance organization and quite often the IT organization when it comes to implementing technology. They have to have that ability to work really well with people from all different walks of life, all different functions, and really understand what it takes to get things done. To that point, you just have those people in an organization who are incredibly resourceful and know how to get the resources they need to be successful, which could be dollars or could be people or whatever it might be, but they understand what it takes to get those resources to be effective. That was always the easiest thing to test for. I think time and time again I’ve seen high performing RevOps leaders, those are the pretty consistent traits. 

Nick Daley (16:53): You touched on a follow up question there, which was obviously you can see a lot of this in their previous experience, resume, speaking to their teams, who they’ve worked with and things – but is there anything specifically in the process that you typically ask for? Or maybe as a case study to get a better sense of these capabilities? 

Bryan Caplin (17:13): I tend to ask questions around examples where the candidate did something for the first time at an organization, not where you’ve done things better or more effectively, but give me an example of where you implemented a process that was new to the organization, or put in a new piece of technology for the organization, or rolled out a new comp plan or whatever it might be. How’d you go about doing that? How’d you get the resources that you need? How’d you get the buy-in? Et cetera, et cetera. 

Nick Daley (17:42) That’s really helpful. I appreciate that. On a slightly different track, especially having done this at multiple different orgs at this point, what’s the number one mistake you see companies making when they’re building out this RevOps function? 

Bryan Caplin (18:00): Well, to my point earlier, you might hire too senior or too junior, so you just get it wrong. You want that person who’s got 20 years of experience, they say all the right things, they’re ready to be scrappy and get their hands dirty and help build something out – but then they get into your organization and they’re used to having a team of a few people, and they’re used to having a fully built stack and all those things. It’s like organ rejection and then obviously vice versa. Someone that just hasn’t done it before can be the complete opposite. That’s one. I think two is over investing in technology. 

There is so much sales tech out there right now. It’s dizzying. It could be very easy to buy a piece of technology for every single thing that you need to get done on the sales project. It is wild and it’s exploded in the last five years. Sometimes tech is the answer, but oftentimes, I think you got to kind of figure it out yourself and then figure out where technology can enable or make a process more efficient or eliminate the human element of it. Too often companies look for the tech solution first without really understanding what the problem is they’re trying to solve. 

Nick Daley (19:29): I love that, spot on. We see this often unfortunately. It is just tough work, figuring out what product market fit looks like and how to scale and outsourcing that to a piece of technology, a consultant and things of that nature, when in reality that’s got to be the founding team and the key exec team’s job. It’s a constant process of iteration, and it’s not until you have full security in that kind of knowledge that you can look to then bring technology into that really to scale rather than figure it out, I think. 

Bryan Caplin (20:04): Exactly. You have got to put in the work and figure out exactly what your needs are before you go spend 50K on a fancy piece of software. 

Nick Daley (20:16): Exactly. Well, while we’re on the topic, we’d love to jump into tools a little bit. What have been the most impactful tools for your RevOps processes today? 

Bryan Caplin (20:27): Obviously you’ve got your core tech stack that any startup leader and operator’s going to need: a CRM, a conversational intelligence tool for call reporting and call analysis, a lead routing tool if you’re heavily inbound focused. But I think for me, what’s been most impactful is a BI tool. The dashboarding and reporting that you get from a CRM is usually pretty basic and probably fine for your first 12 months. But as you start to grow in terms of headcount and grow in terms of geography or products, you’re selling a tool that can ingest all of your data and be manipulated and present trends and analysis in a really streamlined way is found to be super important. I’ve used many out there and each has their pros and cons. We use Sigma at Thoropass, and it’s been a game changer for us just in really helping business leaders from many different parts of the organization really understand what’s happening in various parts of the business, whether that’s industry segments or new business or our renewal rates, et cetera. A BI tool is certainly one that I would invest in sooner rather than later. 

Nick Daley (22:04): That’s really helpful. And maybe while we’re on that topic, the use of data and analytics within the RevOps function, especially as it relates to predicting revenue outcomes and informing decision making. It sounds like the BI tool is a big part of that. Maybe you can go into a bit more detail over what types of data and analytics you guys are typically looking at, how you’re reporting that back into the organization as well. 

Bryan Caplin (22:30): I love it for cohort data, looking at different cohorts of customers and new businesses and how they are trending over time. Seeing if there are trends around when new customers came on board and how are they performing from a retention and upsell perspective – that can be tricky data to pull together and track. A BI tool is really useful for marketing efficiency. Looking at whether that’s your PPC spend and your efficiency there, and how those dollars are translated on the other side into SQLs and ARR, I find a BI tool can be super helpful for that as well. Then on the customer side, really, really helping you understand the renewal trends. What are deals that are at risk? What is it about those deals that are consistent so we can get ahead of that, right? If we’re finding that we’re seeing a lot of renewal risk in companies below a certain amount of ARR or in a certain geography, or maybe we’re working with a junior level person, I want to see that data regularly so I can then use that to focus my CSMs in the appropriate place. 

Nick Daley (24:00): It especially sounds like a shift from being historically more reactive where you’ve got those end of month numbers, to, hey, let’s look at the problem and fix it now. It seems much more proactive, this close to real time data day by day, week by week allows you to as A CRO make more informed decisions earlier. 

Bryan Caplin (24:19): Exactly. 

Nick Daley (24:23): Maybe we could talk about the future a little bit and the future of RevOps, specifically curious how you see the role evolving over the next five-ish years, especially with the rise of some of the tools that you’re probably referencing on the AI side. We’ve seen a bunch of work on AI SDRs and increasing segmentation tools and even creation of materials and cold outreach and things like that. Of course, all the automation that comes with that too. Very curious for your take there, having obviously used a lot of these tools for a number of years now. 

Bryan Caplin (24:55): Yeah, well, coming back to one of the things I said from the outset, I think in the past RevOps would be dumping a bunch of data into spreadsheets and crunching the numbers, and that now is being done by a bunch of these BI tools or certainly AI tools. What that means, I think to be an effective RevOps leader moving forward, is to question, what the data telling us? Translating data into insights and into actions. I think it’s really pivoting to being a strategic thinker, a forward thinker, and an interpreter of the data versus reading out what’s happening in the business. The future of the function is hopefully one that’s even more impactful. It’s saying, okay, here are the trends and this is what we think it means, and here are the recommendations we are making to use the CRO or CMO or whoever it is – the change we need to make in business. It’s hard because that’s a different muscle that’s no longer a behind the scenes, back-office number cruncher. This is someone who’s really impacting the business, making recommendations and delivering insights that the data is uncovering. 

Nick Daley (26:22): Yeah, absolutely. Are there any particular types of tools that you guys are experimenting with or have had success with? We’ve seen plethora of new things in the last 6 to 12 months in particular. 

Bryan Caplin (26:33): There’s a couple of tools that are leveraging AI to mine. A lot of our call recording and pick out trend data from those. A lot of those tools have their own native AI capabilities, but I’ve found them to be fairly ineffective so far. There are some third-party tools that we’ve been piloting that will read your transcripts, and mine the calls on a week-to-week basis, then surface some trends and insights on a weekly basis. I’ll get an email every Monday that says the tool reads 134 calls from last week, and we noticed that this competitor was mentioned the most often and it sounds like pricing was a real challenge for most of your prospects last week and etc… basically taking transcripts and turning it into some type of structured data and insights that you can actually do something with. It’s basic, especially in a high-volume type of business where we’re more on a weekly basis, there’s probably a hundred customer facing calls that are recorded, if not more. It’s impossible for me or our sales managers to listen to even 10% of them, so a tool that can surface those themes and trends for us is really, really powerful. 

Nick Daley (28:06): Absolutely. I mean, there’s an insight from every single call, right? Whether it was a hard no or soft yes, there’s insights from all of them and getting that into one place has a lot of value. As we come to a close here, curious, do you think there’s anything that the operators listening to should keep in mind for the future of the category? 

Bryan Caplin (28:06): I think where RevOps sits is really important. Most folks default to it reporting up into sales into the org, but I’ve actually seen it work the other way. In fact, at Thoropass, it sits in the finance organization, which when I first got here, I was a little bit skeptical of. I’ve always had IT reporting directly up to me, but I’ve actually found it to be a pretty powerful setup because sitting in finance, there’s less bias. When RevOps surfaces some data, I go to my CFO and say, “Hey, we’ve got a big opportunity here. I think we might need to hire a couple more AEs, or I think we need to invest in this piece of technology” or whatever it might be, I’m basing these on recommendations from RevOps, it’s a little bit more credible versus when it sits in sales, it might seem like a self-serving recommendation that I’m making. 

Number two, it’s the nice balance, right? Sitting in finance, they’re not quite as influenced or impacted by what a sales leader may want them to do or a customer success leader. You need someone who’s highly collaborative, even more so if you’re going to set it up that way. Again, incentives as we talked about, will be important to ensure they still have some skin in the game to support sales, but org design, I’m not saying to always structure it this way, but I’ve now seen it work really well reporting up into the revenue org or up into finance, and that was a learning for me from previous roles. 

Nick Daley (30:04): Absolutely. Well, I think with that, we’re up on time here and really appreciate those closing remarks. I don’t know if you want to quickly just talk about Thoropass, and especially for anyone listening, obviously you guys work with a bunch of different startups. What should they reach out to you for or when should they reach out to someone like yourself? 

Bryan Caplin (30:24): Absolutely. Thank you for that. I think if you’re an early-stage founder, you’ll probably find that you’re going to be asked to comply with SOC2 or ISO 27001 or HITRUST, whatever it might be, the alphabet soup of compliance frameworks. You’re going to be asked earlier and earlier to comply with those, especially if you’re trying to win some mid-market or enterprise business. We were purpose built to help companies do that. We are both the compliance automation platform that makes getting audit ready easier, and we are also the auditor, so it’s a one-stop shop, a closed loop ecosystem that basically makes the whole process of getting compliant easy and then we perform the audit for you. It’s a much easier process, lower cost, and one that we’re finding is increasingly the way to pursue your compliance frameworks. We call it the ROA, and like you said, we’re servicing early-stage startups with a few employees up to 10,000 employees who are doing multiple frameworks at the same time. So happy to help, give us a call. 

Nick Daley (31:32): Awesome. Yeah, I can very much test that. Actually, just made an intro for Thoropass before jumping on this call to one of our pipeline companies in the healthcare space, so broad applicability is the way to go here. Bryan, thank you so much. I really enjoyed the conversation on RevOps. Hopefully we can do this again soon and see if some of your predictions come true and catch up from that.