How to Hire a VP of RevOps

Speaker A: When I interview folks, one of the things that I'll do is just sit down and ask them, like, walk me through how to build an inbound engine. How do you determine what an MQL is? How do you route leads? You really want to dive in and think about, like, what is the motion that we want to improve most and how am I going to find the person that's going to improve that? Now if you're, you know, a fifth time CRO and you're like, look, I've built a million outbound engines in my life and I've just entered this organization and the outbound engine is a mess, but I know exactly how to fix it and I just need somebody to update the tools, then great, as long as you've got time to do that, that's great, that works. But I see so many people overlook this and then really fundamental things like defining the icp, properly outlining the process, doing capacity plans and territory plans, lead routing, lead response times, basic things that cause us to win or lose, prospects and leads and opportunities. Qualification criteria gets ignored because the CRO is so busy recruiting, hiring and managing the team and helping to close deals and forecast the. That you've got all these things that are broken in the Go to Market engine and they're kind of obvious. So these are some, some things that you really want to think about before you think about the type of person you want to hire. Welcome to Go to Market Science. In this podcast, we share tangible, actionable playbooks from the trenches, working as Go to Market Strategy and Rev ops consultants for our clients here at Union Square Consulting, and candid conversations with revenue leaders in the market that have been there. Now, let's get into it.

Speaker B: Most VP of Revop searches go wrong before anyone even looks at a resume. A CRO decides they need one person who can do everything, floods them with a hundred requests, and a year later, something hasn't gone to plan. Today, Eddie and I dig into how to actually approach this hire, what to figure out first, and what a company really needs from the role for it to be a success. Hey, Eddie, how's it going?

Speaker A: It's going well. Uh, let me just jump in here. When you talk about something not going to plan, what do we mean by that? I think like most importantly, what we mean is we didn't hit our target. We are not, you know, hitting our revenue number and, or forecasting accurately and all the downstream or upstream effects of that, our revenue engine isn't improving. And so I think the mistake that I see so many CROs make is they try to hire a VP of RevOps or a director or a manager of RevOps, or even build a team of RebOps. And we're updating all these tools and building all these workflows, but it's not actually helping us reach our target. It's not making salespeople more efficient, and it's not helping to turn more marketing demand into actual revenue, and it's not helping to retain and grow our customers. And so I want to dive into this podcast today after writing the article on how to do this in hopes that it helps people out in the market, think about how they want to identify what exactly they need in the VP of RevOps role and how they're going to build the team to do it so we can actually drive revenue and not just have a bunch of people updating tools with no actual impact to revenue from doing that.

Speaker B: So when a CRO sets out to hire a VP of RevOps, Eddie, what's the person that they're commonly picturing in their head? What do they think this person is going to do for them?

Speaker A: Yeah, well, I mean, I don't want to paint every CRO with a broad brush, but I think the common mistake that I see here is that we're looking for this unicorn that almost doesn't exist. So I, I, if you asked me a couple years ago, I would have said this is three different roles in one, and now it's kind of four. So let's start with the basics. Right? Um, first you have like your Salesforce admin or architect, depending on how senior we want to go. And that's somebody who's going to manage Salesforce. They're going to update fields, workflows, they're going to build reports, they're going to, you know, upload data. By extension, if we're using HubSpot for marketing, that person likely is going to manage that tool and learn it. And we've got outreach and zoom info and Gong and the other tools in our revenue tech stack. That alone is a, is a job and there's tons of people out in the market that can do that. And it can be incredibly challenging by itself right now. Let's then add in go to market AI on top of that. So now you're taking somebody who's maybe spent five or ten years mastering Salesforce, and now you're like, hey, I need you to figure out how to use Claude and implement AI native solutions and vibe code tools over the weekend. And fine, we'll talk about that in a bit. That's all well and good, right? And those are really valuable people. But after hiring, uh, dozens of these people and interviewing hundreds of these people, Most of them 95% are really good at the tools because that's what they focus on and that's what they're obsessed about. If you ask them about how they're actually driving revenue, about how much revenue their current company has, about close rates and conversion rates and how they design territories for Outbound, and how they define the, you know, the process to convert inbound leads into revenue. Of course they'll tell you about how they built the lead routing rules in Salesforce or how they updated the scoring model in HubSpot. But when you ask them about fundamentals, when we step away from the tools and you ask how did you architect this engine to actually drive more revenue? This is where 90% of them really hit a wall because they've spent so much time in their careers focused on how the tools work. And oftentimes working for people that are not asking those questions that they don' they haven't spent enough time thinking about the answers. Not that this is rocket science, but it's a unique skill set, just like learning how to implement Salesforce is. So I'll call that the architect rule. Not to be confused with a Salesforce architect, which is just a very, very senior person that used to be an admin, but somebody who actually architects out, uh, the inbound process, the outbound process, the expansion sales process that determines how do we identify the right ICP and how do we build territory plans that are a, ah, fit for the capacity with our team and have the absolute best accounts in those territor, um, how do we build commission plans that really drive the behaviors that we want? These are more, quote, unquote, strategic initiatives. I hate to use the word strategy because I think a lot of people think about McKinsey and a bunch of worthless PowerPoints. But building a territory plan is not a, uh, worthless exercise. It's something that can determine whether or not your salespeople spend the bulk of their time focused on the highest value accounts or whether they waste a lot of their time calling low value targets that are less likely to convert into revenue. So who's going to do that work? And then the last piece would be analytics. And the way that I visualize this is let's imagine this unicorn that we've hired and they're doing all these things that we just mentioned and then when are they going to analyze the data? So imagine that, uh, they're so busy during the week, right? So it's going to be Saturday or Sunday M morning when they sit at their desk, uh, ignoring their wife and kids and they have their big cup of coffee and they're going to sit down and pour through Salesforce and HubSpot reports, uh, or use AI to do this, which we could get into. And they're going to spend four hours slicing and dicing the data and they're going to come back to the CRO on Monday morning and they're going to say, I looked at all the data and these are the leads that are converting and these are the ones that are not. These are the deals we're winning and these are the deals we're not. Here's what's going on here. This isn't just surface level information. Here's where the team is not executing. I probably should have started with that. And who's going to find time to do that? And the question that I'll ask is that if we're going to hire the systems person, which is totally fine, then the responsibility for the architecture and the analytics falls on the CRO. And if you say, look, I can carve out half my time to do that, I can sit down and I can review our ICP and put pen to paper and document out our ICP and then make sure that gets translated into capacity plans and territory plans and the accounts we upload into Salesforce and who my salespeople are calling on, then that's perfectly fine. But if we don't do that, the tools folks will oftentimes build a really elegant technical solution that doesn't necessarily get us the most efficient path towards revenue.

Speaker B: That is a lot. That is so much to ask of one person. Like, what would it take if a CRO or a company was to find a person that could do all of this stuff? What would it take to actually land them and keep them?

Speaker A: Well, I think that's the other thing that's really hard. Like, let's touch on AI just for a moment, right? So the absolute best person out there that's just obsessed with AI, that is, you know, building everything in Claude code and they've implemented a bunch of go to market AI solutions and they're just like working 80 hours a week, just deep into it. That person is so rare and in such high demand that if you're not working for, you know, one of the hottest companies on earth, it's going to be really, really hard to hire that person. We had Kyle Norton on, uh, the podcast and talked about how his team transformed their go to market with AI. And he wrote an article that really resonated with me where he said, look like you're probably not going to find this unicorn. And I'm just talking about the AI unicorn right now. I'm not talking about the do all things unicorn. And he said, look like you're probably better off to just use the team you have and learn these tools, which isn't that difficult. Um, and then you can transform your go to market with AI rather than hoping that you're going to attract this unicorn. Because even if you find them and even if you can afford them, they can work for anybody. And unless you are running the hottest company on earth, they're probably not going to work for you. But if you can find that person, like please grab them as fast as you can, right? But you're still going to need the person that is going to architect out the solution and you need somebody to look at the metrics. Otherwise we're just architecting solutions based on theory and not based on actually looking at what's working and what's not. And that is really, for me, the fundamental difference between a go to market engine that really gets fine tuned and starts to get seriously more efficient and one that doesn't. And if you look at what Kyle Norton's built over@owner.com where they've scaled to I think they're at a plus, $100 million is the last thing I saw. And they've used all these AI tools to like drastically improve things like close rate from 38% to 53% at the time that you interviewed him on our podcast. I mean, these are phenomenal results. These don't happen by vibe coding something over a weekend. They happen by having a dedicated team that is really thinking hard about this. And the analogy that I oftentimes m think of, and I got this from Pablo Dominguez and Matt May who wrote what a Unicorn Knows folks at Insight, um, Partners. Comparing this to an F1 team and you think about how much an F1 team is measuring and iterating every little thing. They've got all these sensors in the cars and all these cameras and wind tunnels and everything you can imagine. They didn't just design the F1 car in a lab over a weekend and set it and forget it. They're constantly improving. And if we want go to market to be a grade, we need to do the same thing.

Speaker B: And this podcast episode isn't meant to be like a plug for our services. Or anything. And it's not going to be that. But I feel like I would be remiss to not mention here that, you know, if you are looking for a VP of RevOps that can fill all these roles or you currently have a VP of RevOps who isn't like the unicorn that can do everything and needs some help, this is all essentially what we do here at Union Square Consulting. We have a team of people that can do all of these things for you at a, uh, less cost than what a uh, full time hire would be probably. Um, so I just wanted to put that out there.

Speaker A: Yeah, I mean we'll layer that in and we're going to try our absolute best not to make this just a, ah, pitch. But the reason that we exist is because, and we'll break each of these roles down is look, if, if you're a CRO listening to this and you can afford to spend 200 plus 300 plus grand on a, you know, VP of RevOps to do the architecture and analytics role, go for it. If you can find, you know, more budget to hire somebody at the same pay grade to do the systems, great. And then do Those people have 40 hours plus per week of work, Then all of a sudden like we get into a tool that they're not familiar with. Like sure, if you're a competent Salesforce person, you can figure out HubSpot, um, you can figure out outreach, you can figure out zoom info really fast. But what about NetSuite? Um, what about Salesforce CPQ? There are tools that even we will not touch. Those are two examples where it's just like you really need to know what you're doing and you need to have specialist expertise at that tool. Otherwise you're going to woefully screw things up. And so the things that I've seen, not just seen, but experienced. I've had three jobs myself where this was the case where I went in there. And keep in mind anybody listening to this, if you're not familiar with my background, I've spent most of my career in sales, but I kind of moonlit as a Salesforce admin, um, oftentimes in dual roles, it is so incredibly easy to just burn eight hours a day updating meaningless stuff. In Salesforce, I did this in multiple roles, first and foremost because I didn't know what I was doing. Secondly, my bosses had no idea what they were doing. Thirdly, I didn't necessarily have enough important things to work on and it's just really easy to spend all day updating Tools, like with no rhyme or reason. And we see this all the time in the market where somebody's hired a relatively junior person and they built this workflow in Salesforce and they built this new report and they uploaded this data and it's like at the end of the day, and did we generate or close more pipeline? Do we forecast more accurately? No. So what was the value of doing all of that? And so it's really easy to say, okay, let's go hire a Salesforce manager at 150k or what have you. And then that person is spending most of their time building stuff that just doesn't need to be built. And so at the risk of just plugging services like the ones that we offer, the real question is, like, what's better to have somebody at 150 grand a year that is wasting a lot of time building things that are not important, oftentimes messing that stuff up because they don't have enough experience and they have nobody more senior to like guide them or somebody at twice that pay grade on a fractional basis that is building better stuff faster. And at the end of the day, you're spending the same or less. I know that that's a shameless plug, but it is what it is. But anyway, let's get back into the thing so that it's not just a shameless plug. My intention for this podcast is if a CRO, a cfo, CEO, anybody is listening to this and they want to hire a VP of RevOps, I want to give you guys tangible takeaways on how to do this. After me having hired dozens of these people and continue to employ these folks and seeing what works and what doesn't work and how, you need to think about this role.

Speaker B: So before anyone writes a single line of a job description for VP of RevOps, what's the work that they need to be doing first?

Speaker A: So I think there's a number of things, right, because we want to avoid falling into this trap of like, just creating this wish list of a hundred different things that we want and then trying to find this unicorn. Because first, we're not going to find it. And then secondly, what we're going to do is we're going to end up settling and we're going to settle for whoever gives us the most compelling resume. And that may not be the thing that is actually what we need. So one of the things that I'd start off with are the grand plans, right? So think about what go to market looks like today and what you want it to look like in 12 or 24 months and what are the most important things that you want to improve? And so instead of saying, look, we need somebody to manage Salesforce and HubSpot and outreach and Claude and these five other tools and Vibe code, you know, go to market solutions and also like improve our inbound and outbound and expansion and also do all of our analytics, which is never going to happen, what's the one thing that you need to improve the most? Um, and I'll probably end up skipping ahead here in my answer, Rachel, um, in terms of like selecting your go to market motions, but the thing I will always push the arrows on is like, what's the one thing that you would improve if you could only improve one thing? Is it your inbound motion? Is it your outbound motion? Is it abm, all bound? Is it expansion? Is it something else? Is it partners? Is it plg? If you could only fix one thing in the business, would it be one of those motions? Or what I oftentimes push even harder on is, what about pipeline management and forecasting? What's the point of generating more pipeline? And if our um, salespeople are just losing deals in the middle of the sales cycle and wasting most of their time chasing deals that they can never close and losing deals that they should be able to close because they're not following the right process. So when I interview folks, one of the things that I'll do is just sit down and ask them like, and this will be like a single question that I'll just follow up on. Walk me through how to build an inbound engine. Give them 30 minutes to answer that question. I'll keep asking follow ups like, how do you determine like what, what an MQL is? How do you route leads? How do you do capacity planning? And this helps that I have some background in this, right? And so I think if, you know, maybe this is a first time CRO listening to this and you don't understand ops as well as you'd like, it could be challenging. We've got tons of resources on our website for this kind of stuff, but you really want to dive in and think about like, what is the motion that we want to improve most and how am I going to find the person that's going to improve that? Now if you're, you know, a fifth time CRO and you're like, look, I've built a million outbound engines in my life and I've just entered this organization and the outbound engine is a mess, but I know exactly how to fix it, and I just need somebody to update the tools, then great. As long as you've got time to do that, that's great, that works. But I see so many people overlook this and then really fundamental things like defining the icp, properly outlining the process, doing capacity plans and territory plans, lead routing, lead response times, basic things that cause us to win or lose, prospects and leads and opportunities. Qualification criteria gets ignored because the CRO is so busy recruiting, hiring and managing the team and helping to close deals and forecast that you've got all these things that are broken in the go to market engine and they're kind of obvious, but the CRO doesn't have enough time to sit down and spend eight hours trying to update the ICP document and then all the additional time to actually take that document from being a meaningless document into something that actually drives action through the go to market engine. So these are some things that you really want to think about before you think about the type of person you want to hire.

Speaker B: So when we tell people that they need to think about which go to Market Motion to improve proof first, how do you recommend they figure that out? Like what steps should they take to identify and decide which go to Market Motion is the actual number one priority that they need to hire on?

Speaker A: I think that there's a lot of gut feel that goes into this because we could do like some deep dive analytics. But if you're hiring your first time VP of RevOps, there's a good chance that the data is an absolute mess and it's going to be really hard to determine this. So just ask like one way to look at this is what's the thing that's most broken? But another way to look at this is if we fixed it, what would give us the biggest uptick right now? This is a place where benchmarks can come in handy. But we always encourage folks to use benchmarks with a grain of salt because some other company selling a different product to a different type of buyer at a different price point is not necessarily going to dictate what works for you. Most companies have really bad data and these are moving targets. And so I have a, uh, deep distrust of benchmarks, especially if you look at things like close rates, because it's like close rates are based on how you define a qualified opportunity. Um, but if you're looking at your close rates and you're saying, okay, like our close rates are 12% right now, that's a good indication that like it should probably be at least 20%. What would it do if you got your close rate from 12% to 20%? And how does that compare to the level of effort it would take to. I mean, that's almost double, right? So how much easier would it be to do that versus doubling your pipeline? I would argue it's a lot easier to get your close rate from 12%, which is pretty bad, to 20%, which is pretty average. Um, sales cycle. Obviously sales cycles are highly dependent upon the product and specifically the price point. But what if you could get your sales cycle down 10, 20, 30 days? I mean, 30 days is an extra. It's called 36 days for easy math. That means you sell 10% more this year. That's pretty significant. What if we could get our average deal size up by 10%? I would argue that if those things are not already pretty dialed in, that's where you want to focus. If they are, and then you say, okay, great, we need to really improve our outbound engine, then that can be a great place to focus. But the question I would ask is if you put all of the realistic resources that you can put into this and you focus on improving your pipeline management and forecasting versus improving your ability to generate more pipeline, which is going to pay off most and fastest? It's probably going to be pipeline management, unless that's already in a good place. And then when we look at different channels, we probably want to look at the type of customer we're going after and what channels are going to make the most sense. And of course, our historic performance. Right. Like we make this podcast for companies that are well past product market fit. So I would just argue, look at what's been working and form a hypothesis around the thing that if improved, will have the biggest uptick for revenue production.

Speaker B: And so what about AI? Because boards are pushing everyone to put AI everywhere right now. How should a CRO think about that in the context of what they actually need from a VP of RevOps?

Speaker A: Well, this is great timing for this question, right? Because we've just talked about the go to market motions and the top priorities. So let me pose a question for any anybody listening to this. There's so much pressure from everybody and we feel this pressure too. I mean, we spend, I spend a lot of my time talking to the private equity firms backing the B2B tech companies that we work with and they're putting all this pressure on us to push AI as well. And we are. I mean, we are working on new AI solutions every day. But to what end? If you've determined that Closing more deals is your number one priority. Then start to ask how AI can help you do that. But even then it becomes kind of a hammer looking for a nail. I really want to start with what's the go to market motion I want to fix most, or do I need to fix our pipeline management forecasting? Then what are the things within that that we need to fix? And we have our go to market efficiency pyramid on our website that you can go to and you can see fine details like bullet point by bullet point, all the different things that need to be fixed for each of these things that we're mentioning. And then you say, okay, like we need to improve our qualification so that we're not chasing deals that have no chance of success. Okay. There are a number of basic things that need to be done to improve qualification, such as sitting down and determine what a qualified deal is before we start implementing AI. In addition to that, if we implement AI, let's say that we want to build an AI tool to help us qualify deals. We have to tell the AI what a qualified deal is. We need to look at our past wins and losses and reverse engineer the deals we are most likely to win and the signals that give us reasons for optimism or concern. Now we have sales methodologies like Medic, Medpic, Bant, Sandler, all these other things, but they ultimately need to be translated into a sales process. All of these things need to be dialed in alongside our ICP before we can feed any AI tool with any relevant context and expect it to produce any decent output. If we just tell the AI, go look at our pipeline and tell us what deals are good and what are not good, we're going to have a really, really bad output. And so I'm all for AI solutions, but it has to be through the lens of what's the thing that, if improved, will drive revenue the most.

Speaker B: So once we have that dialed in, we know exactly what we want out of this VP of RevOps and what we need to improve and go to market. How does a CRO keep a new hire focused on what matters?

Speaker A: So we are really, really big fans of, uh, Go to market ops or RevOps roadmap, which is essentially just following okrs objectives and key results. Right. So let's go back to these grand plans. Let's say that we need to say we're a $100 million company and we need to grow to $120 million this year. And let's say we expect 5% churn. So that's $95 million in retention. And we need to get $25 million from new business and expansion. Okay, how are we going to do that? Well, we have a clear goal of $25 million of new business and expansion. Let's say it's $20 million new business, $5 million of expansion. What does that mean in terms of the pipeline that we need to generate? How many inbound marketing leads do we need? Or how much inbound pipeline do we need? It'd probably be a better metric. What do we need in terms of outbound? In terms of activities, meetings, pipeline, etc. What do our historic numbers tell us? And this is one of the chicken and egg things, right? Like, this is the kind of work that a strategic VP of RevOps would do. Sit down and look at all this stuff and help build out the annual plan. And that may be a great place to start with a new, competent strategic VP of RevOps. But what that then translates into is a roadmap where we say, these are our specific objectives. We want to generate $50 million of qualified pipeline through Outbound, for example. In order to do that, we need to improve our ICP and buyer Personas. We need to run a capacity plan, we need to build better territories, et cetera, et cetera. Again, we have all this stuff laid out on our website. You can go to unionsquare consulting.com frameworks, and then we have a framework that guides our quarter. And this is exactly what we do with our clients, right? So now we say, okay, this is our top priority. We want to generate $50 million from Outbound. In order to do that, these are the 2, 3, 4, 5 things we need to do. Um, obviously we also need to get our team to actually execute the outbound process. Make the call, set the meetings, build the pipeline. And that's a really important thing. And I'm going to glaze over that. And so we've got this all on a document somewhere. And the CRO sits down with the VP of RevOps. They discuss it, the CRO provides feedback, and then there's finally a document that gets signed off on then, for us at least, and this isn't the only way to work, but for us, we work in biweekly sprints. So now we say, okay, great, we got our quarterly plan. What are we gonna do over the next two weeks? And then we say, okay, over the next two weeks, we're gonna really dial in ICP and buyer Personas. For example, you could probably do more than that in two weeks. But just as an example, this is how you get folks focused. The way you get them unfocused is to say, okay, we're gonna add you to Slack and everyone across the team is just gonna ping you with whatever random request they can possibly think of. Hey, like, we need you to jump in and uh, approve this deal via deal desk. We need you to build this commission plan, we need you to update this workflow, et cetera, et cetera. Um, it is so incredibly easy to take anybody, even the most strategic leader, and derail them by just lobbing these random requests at them. And the onus is on the CRO to sit down and say, like, assuming you've hired the right person, that can be strategic, we're going to build a roadmap and we're going to stick to it. And if some new request comes in, unless the house is on fire, we're not going to delay the things that we have to do in order to generate that $50 million of pipeline from Outbound, for example. And this is one of the hardest things for people to do. It's really, really hard to find people that are good at pushing back because everybody wants to just make people happy and keep their jobs. And it's also really hard for the CRO, as they're running around from deal to deal rep to wrap interview to interview, to take a step back and say, hold on a second. I need to think long and hard about like, what are the most important things for us to accomplish in operations. But this is what the best teams do.

Speaker B: Mhm. This is. I think it'd be especially important for a new VP of RevOps who wants to look good and make their new company happy and make their new co workers happy. So they field all the incoming requests that come in and they want to do everything for everybody. Um, I think it's just, it's so important to have those guardrails and have that m. That coverage from their bosses and CRO to be like, no, you need to focus on these things specifically. It's okay to turn down these other ad hoc requests and fire drills, but

Speaker A: it's also something to think through. Right. Like we spend a lot of time talking about the work that we do and the work that makes sense for us. Um, commissions, calculations is an example of something that we've done a couple times. We don't want to do it again. And it's a really slippery slope for a VP of RevOps to fall into because it can consume most or all of their time. Uh, it's also really easy to upset people when things don't get calculated correctly. And oftentimes commission plans can be overly complex and problematic, which is a topic for another day. Um, and you know, between that dealdesk, like the ad hoc request for field updates and uploading data into Salesforce, it's so easy to just consume 100% of the VP of RevOps time. Or even if we're not consuming all of their time, it's like, oh, congratulations, you have a half an hour between meetings, go update icp. It's like people need protected time for deep work. If you want someone to be strategic, it is not going to happen in 30 minute windows between meetings in the middle of the day. Like they have to be able to sit down and focus for a few hours on things or these strategic things will never get done.

Speaker B: Absolutely. You and I both know that more than anyone.

Speaker A: Yeah. And I mean for me, like I do all of my best strategic work early in the morning. A lot of times I start at 7 and I work through 9 or 10. And then after a certain hour of the day, like I'm just spent and I can jump on infinite numbers of zoom calls. But if I'm really trying to get like strategic work done after a certain hour, like, it's just impossible. And I have the benefit of not getting like hammered by a bunch of people on slack all day long partially. And this is just like a little plug for CROs out there. Part of the reason for that is because I've designed a system, uh, for this company not just in go to market, but across the entire company where I don't have people slacking me all day with every little request because we've defined processes and we've built systems and this can be so incredibly liberating. And so I think for CROs out there, hiring a competent VP of RevOps can be absolutely game changing if you hire the right person and empower them. Um, but so many CROs are like victims of like, I've got 18 months to save my job and I've got to hit this number and I've got to hustle and hire people and manage them and close deals and forecast accurately. And I just need this field updated in Salesforce. And it's like, okay, fine, I get it, but if you never take a step back and improve the engine, then you're always going to be a victim of it.

Speaker B: Quick pause. Everything we talk about on this show. Diagnosing go to market ops, prioritizing projects for revenue impact, processes, metrics, insights, building a predictable go to market engine. We've built frameworks for all of it. They're free and ungated on our website unionsquareconsulting.com frameworks. The link will also be in the show notes, so make sure you check that out. All right, back to the episode. And this probably segues in pretty well to this next question. Um, I wanted to talk more about Architecting go to market and you mentioned it in the beginning of the podcast and you're saying all the different, um, you know, jobs of a VP of RevOps. One of them was architecting go to market. So walk me through what architecting go to market actually involves. Um, say the priority is outbound. What has to get thought through with that, and what does that mean for who you choose to be a VP of RevOps and what kind of skills and experience they need to be able to do this?

Speaker A: Sure. So again, we have all this mapped out in our go to market efficiency pyramid and all of, like, the specific pyramids for each emotion that we've built out. You can get that on our website@unionsquareconsulting.com Frameworks link will be in the show notes. Um, but what that means in a nutshell, or the short version is you're going to sit down and you're going to map out, end to end, the definitions and process for how the team does outbound or inbound or partners or PLG or expansion sales, what have you, as well as of course, like qualifying, working and forecasting deals. So let's just talk about pipeline management for a moment and I'll try not to give every example. Right. Because it's all right on our website. Um, well, how do we like, improve our pipeline management? Well, first we need to make sure we've got the right ICP and buyer Personas. Next we need to sit down and think about, like, what is our qualification criteria? When does a deal move into pipeline? Um, what steps do we need to follow? What are the stages? What stage entry and exit criteria? What questions do reps need to ask? What do they actually need to do before they can move a deal from stage one to two, two to three, etc. Um, and then how do we forecast right now, even for me, this is a little bit confusing because what is the difference between that and just implementing Salesforce? Because any competent Salesforce architect. And this is where it's even more confusing, we're using the word architect for two very different things. Right? And salesforce architect is like a common term out in the market. Like, um, there's certifications like Certified technical architect, et cetera. Like, I didn't just make this stuff up. Any competent, like Salesforce architect is going to ask you, like, what stages do you have in your sales process? Like, they might, they might ask what's your entry and exit criteria. They're going to want to know about validation rules and workflows and things in sales that are going to guide that. But where things sort of like fall off is the more. How do I say this? Like, they're not necessarily going to write up a document that says this is our sales process that then informs how we train reps. So there's a big difference between saying, okay, like we need to create a field in Salesforce that says give me the name of the decision maker and a validation rule that says we can't move from stage two to stage three until we've entered that decision maker. That's a technical thing and a strategic thing is to say, we're going to use Med Pick and this is how we're going to use Medpic. And these are the questions that reps need to ask. And this is what it means for a deal to be qualified. And this is what they have to do before we get to stage two and stage three. Now, some of that will then translate into Salesforce. We can still ask who the decision maker is and what their decision making criteria is and all the other things that come out of that sales methodology or whatever one we, we subscribe to. But it's a different person that thinks about how we're going to translate that sales methodology into a sales process and qualify deals and run the process and how we're going to spot deals that probably need to move out of the pipeline versus the person that thinks like, here's the workflows and validation roles and fields that I need to build in Salesforce. Those are two very different roles. And I'll just add that you have to have the strategic stuff first in order to inform how to build the tools. Otherwise, like, you just end up building the tools. And this is why salespeople complain like, oh, uh, Salesforce is so annoying. Like, it's all these fields I have to update and it doesn't help me sell well. When I actually worked for Salesforce, the stuff I had to update were the things that actually helped me close deals. Asking who the decision maker is is a perfectly reasonable question to ask a sales rep. But we've had other companies that ask like 35 other questions that aren't that important. And like the rep is like, every time I Get off the phone. The phone. I have to update 8 million fields and it doesn't actually help me sell.

Speaker B: And can a CRO own go to market architecture themselves if they have time?

Speaker A: I mean they ultimately need to own it at the end of the day. But I think the difference is like, it's one thing for a CRO to say, hey, I'm stepping into a new organization, I know the icp for example, is outdated. We're going to sit down and we're going to update is another thing for them to say. I'm personally going to go and run the reports in Salesforce, run the reports in HubSpot. I'm going to look at all the leads that converted and didn't convert, all the outbound meetings that converted and didn't convert, Pipeline closed one, customers, ltv, et cetera, et cetera. And then I'm going to put pen to paper and in detail I'm going to write down. And by the way, this is fresh because Jerry and I just worked on this again for like the umpteenth time. And I'm going to put pen to paper and define who our ICP is and then translate that into like how we do outbound territory planning and how we, you know, qualify inbound leads. It's one thing to sit down and spend hours and hours of your own time as a CRO doing that, and it's another thing to delegate that to a competent VP of Rev Ops and have them bring something back and then give feedback on it.

Speaker B: So who should be looking at the go to market metrics regularly and what does looking at them actually mean? Beyond the top line numbers?

Speaker A: Yeah, so I thought this was really interesting. I interviewed Tim Strickland, the former CRO of Zoom Info, as well as Scott Sutton, who was uh, one of his VPs of Rev Ops. They had two separate teams that did very different things, uh, and they both reported to the president of the company, which is like a whole different topic and very interesting. Um, and I asked him this exact question and I understand that like many people listening to this are not Zoom Info, nor are we, um, but I wanted to just use this to paint a picture. And what he said is that if The VP of RevOps is not analyzing data and bringing insights about what's working and what's not working in the business, then they're not doing their job. But if he doesn't do that as CRO, he's also not doing his job. So it's a two way street right now. He obviously had a Lot of resources, both on the revop side as well as the sales management or revenue management side to help him. And he wasn't running around like a chicken with his head cut off as you might do in a much smaller company with less resources. So let's be fair to that. But I think that it is the job of the CRO to not only look at the dashboard, but to look deeper and slice and dice the data. Different reps, different teams, different segments, different types of customers, et cetera, and look at what's working and what's not working and try to form hypotheses about areas to double down on, places to cut back, and areas where we want to improve the model so that maybe, maybe what we're doing is not producing the desired outcome, but it's because there's something broken that we could fix. At the end of the day, though, like, the CRO only has so much time to do that. And the VP of RevOps, in my mind, either should do this work or have somebody under them. If we have a big enough team, we can have a dedicated analyst or team of analysts, of course, to do this work. And I think that this is one of the most valuable things that we can do in RevOps and oftentimes one of the most, I don't want to say overlooked, because I think this is obvious for everybody, but just neglected. And then what I would add is there are incredible things that you can do with AI. Uh, this is one of the first things that we built here at USC was an engine built on Claude to do two things. One, to give us a dashboard that is way more robust than what we could build in Salesforce and HubSpot, because those are our two main, like, you know, sales marketing tools. Um, and also a tool that we can ask questions of. Right. And so just to kind of harp on this for a moment, we've got a tool that is giving us all of the go to market metrics in the exact format we want in ways that were impossible in Salesforce. And then on top of that, we have a chatbot where we can ask all these questions, not just of Salesforce and HubSpot, but all of our other data sources like Google Analytics, and then other things that are maybe not relevant for other folks, like our podcast platform, LinkedIn. Uh, um, what am I missing? Uh, our newsletter, et cetera, which I guess is powered by HubSpot, um, and the ability to have access to all that data right there to see it, to slice and dice that data really quickly in ways we couldn't in Salesforce. And also to then ask questions is incredibly valuable, but at the end of the day, it's only as valuable as our willingness and ability to go and look at that data. Um, so I think this is an incredibly important thing, and I think a competent architect could certainly do the job. I'm surprised at how many folks I meet that either struggle with this or just don't like doing it. Um, but it's not such a distinct skill set like being able to, you know, implement Salesforce. I think that the strategic person that's doing the architecture can totally do the, uh, the analytics. Um, whereas the tools person usually doesn't have as firm a grip on the metrics and analytics as you would want. There's obviously exceptions.

Speaker B: Yeah, and I was going to ask this before, but I just remembered, um, and I guess, uh, it goes in line with what you're just saying here as well. How do we incorporate these needs for the VP of revop's role into things like the job description and the kinds of questions we ask when we're interviewing to make sure that we're hiring somebody who's capable of doing these things and has experience with these things?

Speaker A: Well, first I'll just say, and this is like a general hiring thing. This is not even specific to RevOps or go to Market. But, like, one of the. After having read like, the top three books on hiring, my big takeaway was like, the biggest problem with job descriptions is it's really an advertisement for the job, and you're telling the candidate, like, what they would want and what the requirements are. It's not really the thing that you should start with. It's like the last thing that you should write. So before writing a job description for any role in this company, I always write a job scorecard, which is, what are the things that I want this person to accomplish? And so this goes back into the grand plans and then go to market motions. If my grand plan is I want to grow from 100 million to 120 million, and I want to do that by dramatically improving our ability to close deals and forecast accurately and then build an outbound engine that's far more efficient at generating pipeline, then I need to interview somebody around that. If I need somebody that's actually going to architect that solution, um, not just in the tools, but the actual definitions and process, then I'm going to need to go and interview people for those things. I'm going to want to look at somebody that's actually built an outbound engine. Before I'm going to want to look at somebody that has real experience forecasting and helping to improve deals being closed. One, I'm going to want to ask about specific tangible outcomes they've achieved in past roles because it's really easy for somebody to say, oh, yeah, I worked on the outbound engine and we implemented outreach and we did all these things. I built, uh, the entire reporting engine. You're like, great. Well, how much pipeline did you. Did your team generate? Oh, I don't know that off the top of my head. Well, if you don't know that off the top of your head, then you probably weren't that focused on it.

Speaker B: Awesome. Um, so moving on to planning how to manage go to market tech and AI. I know we covered a little bit of this a little bit like, throughout the rest of the episode, but specifically I wanted to ask how often have you seen one VP of RevOps do both the tools job and the architecture go to market architecture and analytics job both really well.

Speaker A: I can't think of anybody that I've seen do that. And there's a simple reason for that, right? Like, it just takes a certain amount of time to get really good at one thing versus the other. And the people that are really good at one thing versus the other have spent X number of years focused solely on it. And I've just. It just would take twice as much time to learn both, right? So, and I. And I. I've worked with people that have learned some level of both. Um, but I think that, like, I'll take myself as an example, right? Like, I have three different certifications on Salesforce, so you could argue that, like, I know what I'm doing in Salesforce and, um, also pardot. And if I took the time, I could probably learn HubSpot pretty quickly and easily. And I'd be like, I'd know enough to be dangerous. But when I compare myself against the folks on our team, it's like night and day difference, right? Despite the fact that I've spent like, I've been implementing Salesforce for like 15 years. Not that I spend any of my time doing that today, but it's like 15 years ago that I started learning that I spend most of my time thinking about the strategic stuff, right? Um, and that just took a certain amount of time and effort. And having been a sales rep was really helpful to that. Having been a sales rep at Salesforce was really helpful to that. Whereas somebody who spent their entire career building workflows in Salesforce will have learned a lot of things that I didn't learn by not spending time doing that and will have not learned all the things that I learned, like sitting in forecasting meetings and actually closing deals and thinking about how to architect outbound processes and inbounds and like, following up with these leads myself. I mean, I will say it's an interesting thing to me. Like, there's a lot of folks in RevOps that have never been in sales. Um, but there's real value in somebody who's carried a bag for at least a short period of time, especially in that strategic role. Um, but we've hired people that have. In between MBAs, we've hired people that just come from, like, a more mathematical analytics background. And it's just a different skill set. It's like, sure, you probably want your strategic VP to learn how to build a basic report in salesforce, how to export data, maybe import data, building a field, little things like that. Like these don't take that long to, uh, learn. But the other stuff, I mean, you can spend years and years getting really good at tools, and that time you're spending, you're not learning about, how do we, like, improve outbound? How do we improve our pipeline management? What are the best forecasting methodologies? There's just a difference between how you configure the tool and how do you think about it strategically.

Speaker B: And on the AI side, does a, uh, team need somebody who's obsessed with AI and knows how to build all these things really, really well, or is that the wrong thing to hire for?

Speaker A: I personally think it's the wrong thing to hire for. I mean, look, like, if you're anthropic and you've got the money to hire dozens of people at, uh, multiple hundreds of thousands of dollars a year and you can attract that talent, then by all means, like, why would you not do that? Right? Um, but I think if we go back to, like, where we started with, okay, like, our grand plan is to grow from 100 million to 120 million, and we want to improve pipeline management and outbound. And here's all the specific things that we need to improve. Like if somebody is a really competent salesforce architect to go and learn how to implement the new AI native tool or how to build something in Claude. I mean, I've seen this firsthand, watching Jerry build a lot of this stuff and implement a lot of the stuff that we've been doing over the last year. It's not rocket science. And sure, it would be nice if Jerry just lived and breathed go to market AI. But what I will say is like the folks that don't understand Salesforce architecture, that don't understand the other fundamentals. Fundamentals. First, ah of all, they might try to like Vibe code, Salesforce, which I just think is the dumbest thing anybody could do. As much as I actually don't love Salesforce, replacing like a truly enterprise tool with something you vibe coded and the things that have taken them billions of dollars to develop, the security model, the, you know, the data model, et cetera. If you just let loose with somebody that doesn't know what they're doing, like, you can create some really serious problems and now your data is at risk and you have all these other, other, other issues versus somebody that says, look, I'm going to figure out how to MCP Salesforce into Claude like it's not rocket science. So I personally would over index on the people that understand the basic tools and are curious and are going to focus on solving the problem that's going to actually help us drive revenue versus the person that's like, look at all the cool things I built with Claude code and look at all the cool things I can do. And now you're a hammer looking for a nail.

Speaker B: That's totally fair. Yeah. I think so much of AI and what's come out with AI has been a lot of hammers looking for nails. It's like, we can do this really cool thing now. Let's find problems for it to solve, which has worked a lot of the times. Like, uh, AI has solved a lot of issues. But. Yeah.

Speaker A: Well, let's just think about like some, some of like the best use cases for AI just for a moment. Right. Like I think the analytics piece is really, really, really big. Um, specifically I've seen a number of reports where campaign analytics are one of the most valuable like ROIs that companies have actually achieved with AI, um, on a more consistent basis. Right. Well, what does it take in order to build an AI tool to analyze campaign analytics? Well, you have to have like all your foundational data in place. And for that you need somebody that understands the marketing tool at a deep level, probably your Salesforce tool as well. And then to take that and figure out how are we going to put that into Claude or how are we going to implement some other AI native analytics tools is not rocket science. But the contrary, Somebody who just happens to be like geeking out on AI for the last two years and doesn't understand sales and marketing tools, doesn't understand the data architecture. Um, you could create Real problems there.

Speaker B: So Eddie, you've had CROs hire you while they were actively searching or hire us as a company while they're actively searching for a full time VP of RevOps. How do those engagements usually play out?

Speaker A: Yeah, and I'm going to try really hard to avoid like the shameless plug here. Um, because this surprised me. I would have thought that we would always get hired or any. And this is like a plug for fractional, not just for us. Right. I would think that it wouldn't make any sense to hire fractional if you're going to hire a full time VP of RevOps. Like we should only be working with companies that are too small to hire a VP of RevOps. But here's what I've seen in reality over the last number of years. First, a lot of folks are looking for some kind of a stopgap. A CRO has come into a new organization. They need to get their head around everything. They don't want to be digging through Salesforce reports and doing all the things that we've talked about here and they want somebody to start working tomorrow. Meanwhile, they're going to launch a search and hire a VP of RevOps and hope to have somebody in seat in three months. I've seen this so many times, right? And so we say, look like you can have an out at three months, like no problem, just cancel your contract at three months and we're all good and we'll do all these things to set them up for success. And what inevitably happens is the person gets hired in three months. They come in, they're trying to meet everybody, get the lay of the land, understand the organization, all the things that you do when you start a new full time job. Meanwhile we're like heads down trying to define qualification criteria for pipeline and update Salesforce and figure out how to get the reps to qualify out all the deals in their pipeline that aren't real. And all this is doing is setting up a foundation of quality data and process and execution for that VP of RevOps to walk into. But then what happens most of the time is that VP of RevOps comes in and sees a bunch of problems, some of which we're working on, some of which we're not. They have a bunch of recurring daily things that they need to work on like deal desk and commissions and updating Salesforce and all these other things. And they're looking around and they're saying, so you guys are laser focused on trying to like fix the outbound engine. I've got These million other things that I need to do. Why don't we continue to partner together? And I know this sounds like a shameless plug, but it is something to think about, especially when organizations are hiring that one and only VP of RevOps that can't do everything. They're like, okay, I'm a strategic person, I definitely need help with the tools. But also, you're already halfway through improving the outbound engine, so like, why don't you keep doing that and I'll work on this other thing? And it's been a pretty good partnership for us. And what we found working with companies is that whether they have a VP of RevOps or not is kind of irrelevant to our ability to add value and for our ability to keep the customer and make them happy. Right. Because they could just cancel the contract after three months. They weren't happy. And that almost never happens. And so that's been like an interesting eye opening thing for me. And I think it just speaks to the thing that you see on LinkedIn every day, which is just how incredibly overwhelmed any person in RevOps is. I have everyone I talk to says they're just flooded with more work than they can possibly do. And, uh, it's just never the case that I hear from anybody in RevOps that they're just sitting around with nothing worth working on. Unless of course you're me. And I worked in like really small organizations, like three or five salespeople, like 15 years ago, where it was like, okay, yeah, there's only so much Rev Ops for a team of that size. Um, but the larger organizations that we work with, they just have this endless roadmap of stuff to do. And the hardest thing is just prioritizing it and finding the person that actually knows what they're doing, whether it's the strategic thing, the analytics thing, or the tools thing that needs to get done.

Speaker B: So if you're advising a CRO on where to start building that team M what are the roles that you point to first?

Speaker A: Well, I think the first thing is you've got to have somebody thinking strategically, right? Because otherwise you're going to end up building systems that don't do the right things, that don't actually help you drive revenue. And this is such a slippery slope. It is so easy to just grab all these ad hoc requests and update this field and this workflow and load this data and run this report. Uh, I mean, there is an endless opportunity in most organizations to do this. And then you wake up a year, two years later, and nothing about the go to market engine is actually improved and there's no tangible impact on revenue. So if the CRO or someone else is going to play that role, fine, that's great. And we're just going to delegate the tools updates to somebody and they are going to be that reactive ad hoc, let me build something in Salesforce with the snap of a finger person, that's totally fine. But somebody has to own the architecture. Next is the analytics. And even if it's just an hour or two a week, I uh, strongly advise somebody have someone looking at the analytics on a regular basis. Otherwise everything's just theory. Right. And the, the slower that you are to look at the analytics, the slower you are to identify something that is not working or that could be improved, that could help you hit your number. And so that's why I think analytics are so incredibly important. The other thing I'll even mention is with analytics, if you ever spend any real time looking at analytics, and I've done this with so many of our customers, the first thing that you always see is a lack of execution. You see that the pipeline is a mess because reps chase deals that they shouldn't be chasing and don't qualify them out. You see leads that don't convert because we didn't follow up enough or we didn't follow up fast enough. You see outbound accounts that didn't convert because we didn't multi thread or we didn't um, you know, reach out via multiple channels or we didn't reach out enough times. And these are basic things that like the data is a mess and the results are poor due to a simple lack of execution. Then you also see all these opportunities where you could automate a lot of that data and save everybody a lot of time. That's why I say like there's limitless opportunities to do this work. But you've got to like think first and foremost about like what's the thing that's going to move the needle for revenue? Mhm. Did I answer your question?

Speaker B: Yeah, yeah, I think so. Um, and so I just have one more question left for us today. If a company can't afford two or more people at the VP level for rebops, what should they be thinking through about finding that one person?

Speaker A: So like I said, if the CRO can play the role of the architect, that's fine. You could hire somebody mid level, maybe even a little bit junior, just depending on the size and complexity of the organization. The tech stack, to manage the tech stack, just know that you get what you pay for. Uh, and if the CRO is not a technical person, then it's going to be hard to manage the technical person and know whether they're doing the right thing or not. Right. Obviously. Shameless plug here. This is the exact problem that we solve for and most of our customers. What we're doing is we're combining somebody at the strategic level and also the systems level that is like well over like the 200k mark. Uh, we don't have a ton of junior resources, but we do have some mid level resources that we can plug in under those folks. And then of course we're looking like tool by tool at what different skill sets people have and what tools our customers need. And so it might be that they don't need anywhere near 40 hours a week of work on the systems, but they've got multiple systems that necessitate more than one person because you can't easily find a person with the skill set across all those tools. Um, and so that's what we attempt to do for folks. But again, I don't want to make this a shameless plug. If the CRO or someone else has time to like sit down and really think through the architecture and then delegate that down to somebody to build into the tools and then analyze the reports and the metrics themselves, then that can definitely work. But just know that you're signing up for a significant commitment. And even if that Commitment is only 10 hours a week, that's a lot of time for many CROs that are trying to figure out how to hit their number and save their jobs.

Speaker B: Well, that is all the time we have today for this ah, topic. But I hope it was um, insightful for anybody looking to hire VP or RevOps or even if they just hired a VP of RevOps and they want to know like what that person should be working on, focusing on and how to keep them accountable to those initiatives. And thank you so much Eddie for getting the um, the write up in the newsletter that you drafted together. That was very helpful creating this topic.

Speaker A: Absolutely. Um, I have interviewed and hired so many VPs of RevOps, so I hope this is helpful for folks, uh, listening because I think uh, I've probably interviewed and hired more VPs of RevOps than almost any CRO out there. So I hope that the uh, experience is helpful. Thanks for listening to the episode. If this resonated, please give us a five star rating and a follow. It helps us reach more people and you get our latest and greatest content without having to search for it. And if you're looking for hands on help in Go to Market strategy and or revops, please reach out to us. We help our clients with everything from annual planning to improving processes in Go to Market, implementing systems to support those processes, and Go to Market AI. We're always happy to offer a free consultation to help you identify the best opportunities to improve your Go to M Market engine with or without our help. You can find us at unionsquareconsulting.com and the info will be in our show notes.