Janis Zech: Hello, and welcome to another episode of the RevOps Lab. I'm here with Cliff Simon. Cliff, I've actually seen you on LinkedIn and in person at an event in Berlin together with your wife, so it's very good to have you on the show.

Cliff Simon: Yeah. Thanks for having me. That was really fun. She doesn't get to come along very often. We have three small kids, so for her parents to be able to watch them for us to get out to Berlin was really special.

Janis Zech: Yeah. Glad you made it. It was a cool event, and there's another one coming up next week in New Orleans where we'll see each other. I think you're speaking at RevOps AF and then also in Berlin. RevOps AF in Berlin. You know? But before we jump in, like, who are you? What do you do?

Cliff Simon: Oh, man. I think I'm many — I'm a Roman to the Romans. Right? But my background's in go to market. I've been in sales in one way, shape or form for about the last two decades now. And I've spent time in zero to ten, zero to fifteen with Carabiner — zero to eight in like twenty months, which is crazy. And I'm the CRO at Carabiner Group. We're a part of a larger organization called SBI Growth, where we help companies tackle all the challenges of the office of the CRO. So what does it mean to actually help a company be efficient and grow, especially in this economic climate?

Janis Zech: Yeah. I mean, it's a topic that I think a lot of folks are interested in, and it couldn't be more relevant. I think it makes or breaks companies, and so today we're gonna talk about what RevOps can do to drive enterprise value, which I think is a very, very important topic. You talk to a lot of folks every week, right? Meet a lot of folks. So what are some common challenges? And that doesn't need to be necessarily RevOps related, but in general. Right? With regards to go to market, what are some of the core challenges folks are facing there outside now?

Cliff Simon: Sure. I think there's probably, like, seven to ten standard problems that you'll run into as you're growing as an organization. Are you launching a new product or a new go to market motion? How do you drive sales productivity? How do you make sure that you are evolving your revenue modeling and you're accounting for macroeconomic trends? How do you drive commercial efficiency? Maybe there's investor problems. Gosh. You could talk about things like technology adoption, multiple CRMs, all the things that sort of come with M&A, churn, NRR, GRR issues. So there's a bunch of different ways we could go with it. Right? Has organic growth stalled?

Janis Zech: Yeah. And I mean, I think it's always in context of the maturity of the organization, how much revenue they make, right? The complexity of their go to market engine they've built. And I mean, if you think about, right, like, I mean, if you talk to the executive suites in these companies, like what themes do you see to drive enterprise value? Like what would you say are the core themes they are thinking of? And, you know, how do you then, like, jam with them to get them there?

Cliff Simon: The jamming is the interesting part. I think there's four main levers that you pull. Do you have the right go to market strategy or set of strategies depending on the types of motions you're running? Do you have the right go to market processes and operating cadence? Have you applied and memorialized those processes into the appropriate technology, and are you able to get the right data and analytics out of it? And then how does all of that work its way through to enablement? Right? Do you have the right people in the right seats with the right skill set with the right coaching and teaching and set of processes so that they can go out and execute.

Janis Zech: Okay. So we have four topics that you typically see to drive enterprise value. Maybe we can just go through them one by one and tackle those in greater detail. So with regards to go to market strategy or strategies, right? I mean, obviously it's important, right? I think we don't need to talk about that, but like, you know. I think that the challenge with strategy is always like that. It's actually a lot of uncertainty, right? Like you basically need to do something for a very long time and when you start it, it's not that clear that strategy is the right strategy. That is often the big challenge with strategies, right? But in your mind, how do you develop the right strategy for a specific business? And I'm happy to dive into a specific example or so, but curious, like, you know, how do you even know what strategy you're running and then, you know, what would be the ideal strategy?

Cliff Simon: I think there's a couple different ways to think about it. Most people start the strategy, I think, a step too late. They're not considering the importance of the ICP. Do we actually have that aligned and do we know who we're trying to solve this problem for? Right. That problem market fit kind of stage. You have to work through that first in order to make sure that you have matured enough to get to a product market fit. Once you're at product market fit and you've actually done a bunch there, now you can solidify the strategy. So in those early days, it's experimentation. Just because you're selling into a certain segment or vertical doesn't mean that's the right segment or vertical for you. It just means that you're able to sell there. It doesn't mean that you're gonna naturally be able to keep those customers or keep them from churning or be able to drive expansion revenue. So those are all things that you have to be thinking through. Now really good cohort analysis. And this is why, like, none of those growth levers really work independent of one another. They all have to work in concert. I'd focus on the ICP. Are we looking at the right customer? Are we thinking about the right problem? Once we figured out the right problem, now we can start building a process around how do we get customers to understand how we fix that problem or how we drive value for them, right? Ultimately, if you're driving value for your customer, you're gonna drive value for the enterprise.

Janis Zech: I think this is so interesting. I mean, the ICP is obviously framing where a lot of people in the organizations work, right? Like, what accounts are you actually targeting? Who do you call? So it actually redirects almost the energy of the entire organization. And then the second thing I find really interesting here is understanding the problem and speaking to the problem. I'd always do this website check and I think, I don't know if any of you follow the Fletch guys, they are basically doing website positioning and messaging consultancy. And it's so interesting because they typically share examples where you go to the website, you read it and you read a lot of value statements like, okay, this is basically the outcome, but you have no clue what the company does. You only know that they do something very, very great, but you don't know how they do it. Like, how do you fix that? I mean, that's like a quite important thing. Right?

Cliff Simon: It's funny. I went to a Pavilion CMO summit, the first one they did back in San Francisco three years ago, and I got to listen to Lottie speak on stage, and I realized I'm actually, like, a product marketer at heart because all I do is positioning and messaging all day. I think you have to go out and listen to the customers and spend time in market. If you are a go to market leader, you need to be in the market talking to your customers. If you're not talking to your customers, you don't actually understand with a high level of certainty the problems and challenges that they're facing day in and day out. Because you might think that your solution solves for x when, in fact, it's solving for a little bit of x, but mostly y and some z. Right? So the majority of the value was they bought your technology because they had that particular point need on x, but they found so much value in how you solve for y, but you're never talking about that. So you need to go out and actually see what's being effective in the field. And then you take that back, you internalize it, and you adjust accordingly.

Janis Zech: So let's assume we got the ICP, we got the messaging, we got the positioning right. What else would you say matters on the go to market strategy? I mean, there's so many other pieces, right?

Cliff Simon: How do we think about pricing? How do we think about competitive landscape? Are we going upmarket? Are we going to go SMB? Are we just going for a land and expand model? Are we trying to win the whole hog on the first bite? There's a lot of different ways you can tackle it. And I think a lot of those pieces are going to be determined by your overall corporate strategy. Is the goal to continue to raise round after round after round and burn through other people's money in order to drive growth? Are you looking for durable and consistent growth? Are you looking for M&A in a certain time period? Right? Like, are you trying to leave meat on the bone so that way when someone comes in and acquires you, there is a whole another market segment that you know this would go well in and you've done experimentation, but you haven't chased after because you want to leave that as a growth opportunity, right, to make the asset look more valuable. There's a lot of different things that you can do from that strategy perspective based off of where you want to take the company.

Janis Zech: Yeah. We had Jacco on the show last year and I think there was this framework or notion that below ten million in ARR, there should be only one go to market motion. Me as a founder, I talk to a lot of companies that are like below ten million in ARR as well. I would say most of them, it's a little bit more fluid. Curious what your take is on that.

Cliff Simon: Yeah. Jacco's got a good mind for that. I might argue five to ten instead of ten as a hard stop. But I think if you've been able to grow with one motion to ten, your likelihood of being able to bolt on additional products or inorganic or go into a different market segment is a lot stronger because you've got a more rigorous backbone supporting the enterprise.

Janis Zech: Ask the question again. I'm so sorry.

Cliff Simon: No, I think you answered the question. I mean, you know, I think ideally, right? Like everybody wants one thing and do that really, really well in great detail. And then, you know, you basically just grow to one hundred million ideally. Right? The question is, like, how realistic that is. I mean, it's super, super difficult. Right? And we think about the number of companies that don't even make it to a series A, let alone a B or C. I think the bigger challenge for most companies is they get distracted, especially over the last couple of years where you've had significant macroeconomic headwinds and then you've got AI. And everyone's trying to figure out what to do with AI. Right? How do I integrate into my product? I think people are just getting to the point where they're trying to really significantly integrate it into their go to market teams. But even, you know, just like a month and a half ago, we heard from some very large companies, the only place they're using it is marketing. So there's a lot of work to be done there.

Janis Zech: I fully agree. I mean, we are basically in the revenue AI space and I think there's an internal saying here that you have to build really good software and then AI is one way to accelerate that software if you want to summarize or predict better. There's a lot of real use cases there but then there's also many others where you just don't need it and it's also not a hard requirement. So I think we had Christina from Forrester on the show actually yesterday and she stated something that really resonated with me is like, okay, similar to what you just said, right? Start with your customer, understand your customer, understand your corporate strategy and your annual plan, and then think about what problems from the RevOps perspective you should actually tackle to drive enterprise value and really question what problems matter because you can't do everything and you have to prioritize. And I think maybe that leads us to the second kind of pillar you outlined, right? So let's assume we have a great strategy. Always assume that we have a great strategy. We'll find out maybe in two years. But let's assume we feel good about it. We aligned about it. The C suite, RevOps, everybody has rallied around the specific strategy. Now, what are the processes you need to put in place to bring it to life?

Cliff Simon: I think the most important ones are the places where you typically see a handoff in between different departments. Those weak links, as you're coming up, it's really easy to just grow in a silo. So eliminating those as much as possible. Right? Marketing to sales, sales to implementations, implementation to CS. I think those are the natural breaking points. Other than that, it's the standard thing. Right? It's just so many of us build, build, build, build, build, and we see traction, and then we forget that we need to check off ten boxes instead of six. Right? Because we don't need that thing today, and we'll get to it later. So making sure that you've really thought through the reasoning why you're going with the first and last touch attribution model. Right? How do you think about — oh gosh, now I'm gonna get into comp — but, like, making sure that you're aligning compensation accordingly across the team. And that goes back into strategy. Right? I think one of the problems we have with attribution all the time is that we're paying people based off of attribution instead of paying people off of actually getting things to the door. You know, you talk about Jacco and you talk about the revenue factory. Right? We're all supposed to be on the same team going towards making this widget, which is revenue. Shouldn't matter where it comes from, only insofar as we understand how to drive more revenue. So marketing versus sales versus the SDR team, wherever that happens to sit. Right? Those types of processes. Obviously, we need to understand what a buying cycle looks like. How does the customer journey actually operate? And how do we then align our buying cycle, our seller's journey to that so that we can coach to it, so that we can get the right metrics out of it, that we can understand where people need help or where things are falling apart because of either personnel or infrastructure or just lack of good process. I think those are some pretty prime examples.

Janis Zech: Yeah, yeah, yeah. So avoiding leakage when drop offs occur. And I mean, obviously, it's one thing to just write down a process on a whiteboard. It's another thing to get people to actually follow it. Any tips or tricks how to improve that?

Cliff Simon: Well, for us, when we're typically going in and building, we're pulling in people's best salespeople. We wanna know what they're doing that might be different from the standard process because there's one thing really good salespeople do is they deviate. But they do it in ways that actually make sense. Right? You have to allow for that ten, fifteen, twenty percent of leeway from the process because the process shouldn't be super, super rigid, but it's necessary. And you take those successful folks. You show them what you're doing. You give them agency. Everyone else sees that they're using the process and that they're adopting. That drives a wider net of adoption. Right? Because everyone wants to be doing what the best people are doing, the most successful people are doing. You do the same thing in marketing. You do the same thing in CS. Give the frontline boots on the ground folks agency. Make them feel like they're part of the process, I think. Far too often, CRM and the associated tech stack has been something for management, and you need to focus on the end user. In this case, as a RevOps professional, my customer is my internal teams.

Janis Zech: Yeah. I mean, we actually recorded an episode on RevOps discovery, and I think the main theme was, like, start with understanding how things are done and how successful folks do it so that you can learn from that. And then I think the other piece, right, and you're just alluding to that, right, if folks don't have buy in, they just won't follow the process. And I think processes, right? I think in RevOps, we talk a lot about processes. We're quite excited about processes. We're all process people, but the reality is that a lot of people on the end user side hate processes. They really do. They feel like it slows them down. It doesn't give them enough leeway to basically do their job at full potential. And so I think this is kind of what you're alluding to. How do you find the right balance? Probably sitting with the best folks, I really like that. I think that's something you can do tomorrow. Go out, go to your top performers, and just shadow them for two days. You'll probably learn a lot.

Cliff Simon: A hundred percent. Right? You're gonna learn more about the business. We're onboarding two new guys right now to our team, and they're sitting through some training. They're very technical. Right? Seven plus years experience on Salesforce. One's about to get his ARC cert. And I had him sit down and just listen to a bunch of calls. He's like, I never thought about this from the end user perspective. I was like, I'm so glad you're getting that now. Because if you don't think about the end user, you're ultimately just gonna build something that's technically proficient or technically great but doesn't actually get the job done. And what I've found with most high performers is that they develop their own workflow. And if you drive any significant deviation to that workflow, their production drops off by, like, half because they've become so attuned to working in this very set pattern where they know where everything is. They know how to give you what you need. They know how to report on it. They know how to hit the number, and they figured out that motion. And then you start throwing monkey wrenches at it without giving them buy in, without explaining to them the rationale for any changes that might be being made. It's a recipe for disaster.

Janis Zech: Yeah. Yeah. So let's jump to enablement. It's one of those topics like, you know, is enablement part of RevOps? Is it not? Like, where should it report to? Any views on that?

Cliff Simon: I don't know. I think I've seen different — I love it rolling into RevOps because, again, I think RevOps is a strategic function, not a tactical one. And if you are in charge of the team that is making all of these system changes, all of these process changes, wouldn't you also want that same team to be the one that's making sure that those things are being taken care of, nuts to bolts? Like, you own the entire RACI. Just carry it through.

Janis Zech: Yeah. A hundred percent. I think it's so important. Right? And it alludes to what you just said earlier on the process side, right? But I think there's the kind of, let's say alignment and process enablement perspective, then there's the customer enablement perspective, right? Like how do you talk? How do you do good discovery? Basically folks that have been typically come out of sales. What is that to you? How does a good enablement person look like in your mind?

Cliff Simon: Empathetic. They understand the strategic needs of the business, and they're able to effectively communicate the reasons these changes need to happen. And they have put together a consistent training platform in order for people to be able to walk through that, whether that's in a formalized LMS or you're doing it in some Google Docs kind of thing, whatever it has to be. Right? It has to be well documented. It has to be something that people can walk through. But that person needs to be able to speak at both strategic levels so they can understand what's going on in the business, and they need to be able to be on that tactical level day to day and work with the team. And they have to have a passion for working with the team. If they don't, then it's gonna fall apart.

Janis Zech: Yeah. And in terms of measurement, I mean, how do you typically measure enablement folks?

Cliff Simon: Oh, man. It's like the rest of RevOps. It's tough because you don't have a direct influence. But like the larger RevOps org, I would be looking at the delta in key metrics. Right? Have we seen ACVs increase? Have we seen sales stage duration decrease? Have we seen overall sales cycles decrease in time? Are we seeing better conversion rates in different parts of the funnel or the bow tie? Right? I think when you start looking at those — again, I'm a big fan of the data model — if you start seeing those one to two to three to five percent increases in conversion, that has a very wide ranging impact on the company. So you have to track it over time because a one to two percent increase across three to five areas is massive. But it takes time. It takes consistency, and it takes a desire and patience from the organization to get there.

Janis Zech: I love this podcast. I can just ask you any question and you have a good answer. So we're totally going somewhere. And I'll just keep on pounding the questions.

Cliff Simon: I told you, you just drive, man. I'm here for the ride.

Janis Zech: Yeah, no, I think that's awesome. And a topic that comes up so often, how do we measure our RevOps? How do we measure enablement? It's so clear on the sales side, maybe a little bit less clear on the CSM side, definitely less clear on the marketing side, I would say. But RevOps enablement, super challenging and the delta model makes so much sense to me. I think it goes back to the overall topic. That really drives enterprise value. That is essentially the scientific way of go to market, measuring, understanding, improving, trying, right? Then there's the external factors that can completely blow these numbers. But I think, we've lived through so many external factors in the last four and a half years, I'd say that the constant now is change. Everything's gonna be a challenge, right? So in that way, like when it comes to the enablement piece, part of it too, like understanding where your people are spending their time. How can I make sure that my best sellers are spending their time talking to customers?

Cliff Simon: Yeah.

Janis Zech: I mean, this has always been our vision. We basically automate all these repetitive workflows like CRM data entry that everybody hates and often just doesn't happen. Like the meeting prep, notes, follow ups, the methodology compliance and even the way you do a deal review or forecast meeting where often a lot of things have to be prepared or they don't get prepared or you look at the wrong metrics. And so how do you build a system that really helps you execute deals better, forecast them accurately and focus on what really moves the needle. And so I think our concept is not like, okay, we replace the sales folks or the CSM folks with AI. They'll be there. They'll just be supercharged and kind of in this 10x engineering idea, have a lot more time to do demos and follow ups and really focus in on strategic discussions with customers instead of getting bogged down by annoying stuff that really like good software and AI can solve by now. And not everything, but more and more, I'd say every month. So I think that's actually a really cool future for the overall community in go to market. I mean, we should talk a bit about data and analytics. We went from go to market strategy, process, enablement to what is really under the iceberg in the water, not seen by necessarily all the folks in the field, right? But that happens every day. What would you say is like some of the biggest challenges you see on the data and analytics side?

Cliff Simon: Dirty, incomplete data sets, lack of adoption, driving incomplete data — you know, makes it so you can't trust it, right? Or people just filling things in because they're a required field. So that's always fun. I think the harder part is there are all these systems, there's point solution data everywhere, but nothing's actually pulling that all together to give you that — to use a Salesforce term — that customer 360. So how do you actually understand what's going on within your organization, within your customer base? Because nine times out of ten, you don't have that full understanding of your customer health data, your top of funnel data, your month over month churn. Like, asking for that stuff from your RevOps team usually takes days, if not weeks, to get. Those are all things that every CRO wants on their fingertips like that. Yeah. That's a challenge.

Janis Zech: Yeah. And then, right, like, there's the different — you just touched on the data model. There's the different layers of data, right, like from kind of the investor metrics fully down to kind of the volume data or quantitative data that is just basically measuring, I don't know, like a conversion rate or so, or even just an input factor. Measuring like fifty thousand people that get a nurture email from us every month. I think one challenge — and that's something we're observing in the market — is how do you be able to kind of navigate up and down throughout the hierarchy of data? And you see maybe your, I don't know, conversion rate dropping. That's great. You should be alerted. You should know that. Many don't know that. But then, you know, to basically understand the root cause, right, and dive in. Is that conversion rate dropping because we're doing a bunch of experimentation in a new industry? And it's dropping the overall number, but in our traditional business, we're actually doing better than we have in the past. Right? We need to be able to bifurcate that and dissect that data.

Cliff Simon: Yeah. Yeah. Yeah.

Janis Zech: Would you say on the data side? Right? Like, I mean, you already touched on siloed data, missing data, incomplete data. What's your take on solving that? It's very hard to solve, and there's no easy answer to that. I get that. But what are steps or quick wins you would recommend to get started?

Cliff Simon: Just a high level of enablement across the team to make sure when people are creating things, those who have the ability to, that that's being done with diligence and care. Because I think a lot of it — oh gosh, we've got so much going on here in the US too when it comes to, like, abuse and fraud and diligence and care — like, if we had salespeople or marketing people who just cared a little bit more and actually took the extra five seconds to put in that field that maybe isn't required but we know helps, I think that's really good. The hard part is there is no one place to go and get good accurate data. They all have problems. I think the best dataset I've seen is something like eighty five, eighty six percent accurate. So how do you go out and trust it? I think that's really hard for a lot of salespeople. They wanna be able to go in and trust it. So that's a big challenge. Or you lock it down, and only your admins can do anything. But then that slows down your go to market. Right? Because every time you need a new account created or a new contact added or anything, you have to go through a gatekeeper. And while that keeps your data pristine, it slows down the pace of business. And any time lost now, man, you could lose a deal. Right? First to act, first to respond. So I think there's a lot of challenges when it comes to that.

Janis Zech: Yeah. Yeah. A hundred percent. I mean, my co founder Philip and I, we recorded an episode on Salesforce data hygiene, specifically going through a bunch of different good wins and solutions there. So if you're interested, I mean, just listen to that. There's also a cheat sheet on our getweflow.com slash RevOps hub where we host a bunch of cheat sheets and guides and stuff like that. But, yeah, I fully agree. I mean, it's a big topic. I feel like, we went through, I don't know how many questions. I think this was probably the podcast with the most questions asked most swiftly and answered with a lot of detail. Anything else you would add about driving, like, RevOps driving enterprise value? Anything, you know?

Cliff Simon: I mean, we talked about this at Arise, right? If you want to drive value, you need to understand what your stakeholders need. You need to be in tune with the C suite and need to understand what the board is demanding. Right? Where is the business trying to go and what challenges is it facing? And how do you take those and tackle them head on, both independently and as a thought partner to the rest of the C suite?

Janis Zech: Yeah. I think that's a great closing remark. Before you go, what's the book you would recommend or report or so?

Cliff Simon: Oh, man. I normally say Extreme Ownership by Jocko Willink. Something I've given to everyone that's ever worked for me. I think it's really — the one I just started reading on the marketing side, of course, is Courageous Marketing by Udi Ledergor from Gong. So I'm only a little bit into it, but, you know, got the nice little signed copy. So that's nice.

Janis Zech: Yeah. Udi's great. I mean, done a great job for sure. Hopefully, I'll be done with that by one of these plane trips in the near future.

Cliff Simon: Awesome.

Janis Zech: Cliff, thank you so much for joining. It was fun chatting about all these topics.

Cliff Simon: Yeah. Thanks for having me. Really appreciate it. I guess I'll see you next week.

Janis Zech: For sure. For sure.