CRO Confidential: Guild Education SVP, Go To Market Strategy, Operations & Enablement Cherishma Shah

Hey, Saastr fans! Welcome to another episode of the CRO Confidential podcast. I'm your host, Sam Blond. Today we have, uh, an incredible guest, a really close friend of mine, former colleague, and the person I consider to be the best revenue operations leader on the planet. In addition to that world record, she also holds the world record for longest job title, the Senior Vice President of Go-to-Market Strategy, Operations and Enablement at Guild Education, formerly held that same role at Brex alongside me. Tarishma Shah, I'm ecstatic to have you joining me here today and welcome to the pod.

Thank you, Sam. And you're not the first one to make, to comment on, I would say comment on the length of the title or just how little it actually says about what we do. So thank you.

It can be both very literal and also nondescript depending on who you're speaking with.

And then we can add some acronyms and make it even better.

Exactly. We were joking before we jumped on, SVP GTM SOE, something like that.

There we go. There we go.

It's really nondescript. Okay. So today's episode, as one might expect, is going to be all about revenue operations, sales operations, go-to-market operations, pick your poison related to the sort of terminology you'd like to use. This is a topic and function that I care deeply about. And as context, prior to learning more from Charisma, most sales leaders, myself included, start in sales. Um, and so my background, and I think that the sort of common path for VP of Sales, CRO, um, uh, depending on the leveling of the sales leader, is something like start as an SDR, promoted to an AE, promoted into sales management, and then you sort of progress your career through that, uh, uh, um, promotion path. And the skills that are required through that experience lack many of the operational skills that are required for a revenue org to be successful. And so the things that come to mind most immediately are things like systems. You know, I'm certainly not like a technical person that is in and out of Salesforce and updating the way that opportunities flow and which fields are required, those sorts of things. Anything that's process related. And then Trishma, where I think you spend a lot of your time around like data analysis and driving strategy from the trends in that data. And so enter this operations function. And I, as I mentioned before, sort of something that's near and dear to me, I attribute so much of my personal success and the success of the teams that I've been a part of to this function. And Trishma, specifically to you as it pertains to Brex. And so with that, let's jump in. Why don't we set the stage a bit and tell us a little bit about your background and what you're up to today?

Thank you, Sam. I will say that's a very hard act to follow now that you've set me up, but it has been incredible working with you and knowing you as a colleague and as a friend. So I'm excited about the time we spend together here too. So in terms of my background, I have a background that one could consider both unique but also common for this kind of role, and I'll explain a little bit more. I started my career as an architect and planner, right? I know you don't think of architecture and strategy, SOE, together, but here we go. And that's where kind of the uniqueness ends. And then after that, went to business school, went on to do consulting, worked at a large company, and then went up to more of the startup crowd, or not even like a complete startup that's scaling, right? And I think we'll talk a little bit about that scaling in a bit. And you often see that for this profile, right? Some people who have that kind of background. And then the biggest things that I have solved for and continue to look for in terms of what I take on are around, I look for, am I solving some of the biggest challenges that can have significant impact on the business? Am I constantly learning, right? That is very important. And then finally, am I working with incredible people? So, exhibit Sam. I am now a mom of an adorable 8-year-old, and I live in the Bay Area, and I lead the strategy ops and enablement, SOE function for Guild. And a little bit about Guild, this is like the mission of the company is to unlock opportunity for America's workforce through education, skilling, and career mobility. I'm very proud of that mission, so. Yeah, that's me now.

Amazing, amazing background. You're very humble as you talk through your experience. A couple things that stand out that I think might be helpful to others when looking for the type of profile, um, and we'll talk through about a bit of the evolution of this type of role as well. But Trishma, prior to joining Brex, you were at McKinsey for a number of years doing management consulting and then had sort of like what I will call real-world experience. You would probably do it better justice by describing, but you were at Google for a number of years, which is interesting because Google is such a large company compared to Brex prior to you joining, but it seemed that that mapped far better than maybe like a traditional sales role for whatever reason.

Yeah, I think that's a really good point, and I think we'll talk about this a little bit through the conversation as well as we think about like what does good look like in this, in this role and in this function. And oftentimes what I've noticed is having someone who's worked in the same industry, right, or having someone with deep type of customer knowledge, right, like enterprise versus B2C, like that may not be as— while it's great to have, right, because they are able to snap really quickly to say understanding what an enterprise sales cycle looks like. But at the same time, I think what is more critical is to get the right capability mix Right? Like, are these— are these people strong operators? Can they roll up the sleeves and actually think about day-to-day processes, connect the dots, and also take a step back and think long term, think proactively about what do I look— what do I need to look— worry about 3 or 4 quarters out? So I think it's what I have seen even as I've built these teams before, is that it's that profile that becomes much more important than the industry experience. So.

That makes a lot of sense. All right, well, I, I think the way that we'll structure this conversation is a little bit of a journey through the startup's life cycle. Um, and we have an audience that ranges from, uh, founders that are just getting started, hopefully on the way to building a really big business, and it might just be a couple founders, all the way to some of the largest businesses in the world. And so why don't we start, um, just sort of like the, the company life cycle and We'll start at a bit of the highest level. And before we even jump into like, when is the right time to invest in this function, why don't we start with how do you define revenue operations?

Yes. And why is it revenue operations instead of SOE?

Right.

Like, so I think it's a very interesting question, Sam, because I think it's important to, to tie that to a number of different titles and roles that you will see across different companies. So I've heard this being called just plain go-to-market. I've heard this team being called go-to-market strategy and ops. I've heard this team being called revenue ops, and sometimes even just in the earlier stages being called like sales ops or marketing ops, right? That said, I think it's also important to call out that this is incremental to what a traditional sales ops or marketing ops function looks like, because revenue operations essentially touches multiple functions across the sales cycle, right? All the way from like starting with marketing and sales and thinking about all of the specialists that get involved, which can differ based on the industry, to things like customer success, implementation, etc. So it's across the customer journey. And then it also generally starts with— I think the way I would think about RevOps is it is, it is, it includes The remit includes things like laying out the operational foundations for how do we think about all of these functions and how do they grow, right? An example could be, I think you mentioned this, right? A consistent sales methodology, or how do we think about territories and incentive plans, all the way from that. And then it also includes aspects of sales and go-to-market strategy, which is how do we think about our ideal customer profile? What are the markets we should be going after? What does the coverage model look like? To be able to support those markets. And the system support that you talked about, which is like, okay, now that I have the right processes in place, how do I put it into systems so I make it repeatable, right? And I increase the efficiency and productivity of my teams. And then finally, I would be remiss not to mention enablement. And this is something that I have seen come in and out of sometimes like a RevOps function. However, I believe enablement is an integral part of revenue operations Because it has not just like the content of enablement, but also the overall— that's why the process of it, right? What is the value chain of information flowing from whatever the source is to the actual audience? And being able to tailor it by audience becomes very important.

Oh, it makes a lot of sense. A quick recap, at least of my interpretation of what you said, which is this function of operations as it applies to any go-to-market organization, incorporates the following: systems, process, some like strategy that is a combination of data analysis and driving strategy from the trends that you realize in data, and enablement. And sometimes this function begins dedicated to a specific department like sales, marketing, maybe even like customer success. And as you expand to include something like revenue operations or go-to-market operations, that's tying the operations of all of these different functions together.

I think that's exactly right. And I think you referred to it. I will just highlight, like, I think there is a, there's a pure operational component as well, right? That goes beyond systems and processes, which is like, hey, how do I think about what are the key metrics that matter for this business? What does success look like? How are we doing against those metrics? If you're not doing well, do I need to dig deeper and understand why we're not doing well. So that, like running the business aspects of both the metrics and then what are the actions we need to take, right? And then making sure we're taking those actions, like that is also an important part of how you would think about this team.

Perfect. Okay, so we have a bit of a definition of what this team does and its remit and what success looks like. So let's start along this sort of company journey from the very beginning. When do you think is the right time to hire a dedicated sales ops, revenue ops, just any person fulfilling these duties?

Yeah, so I think you— the way you teed up the question is exactly right. What I have seen, generally seen, is that it starts within a function, right? Like, generally what you see less of is someone coming and saying, oh, I need a revenue ops team, right? You generally start seeing a sales ops person being hired or a marketing operations person being hired, right? All the way from saying, hey, I now have more than 2 sellers. Now I need to start defining the sales methodology, or I need to set standard processes, or I need to think about incentive plans and quotas. Like, all of that starts happening. And then for marketing, I need to find someone who can help me with campaign management. How am I leveraging the right tools to be able to scale? So I think you— that's the way you see, um, It generally lead in. I think the one thing I do wanna call out though is oftentimes when we see this hire, we see them as a, and this is shifting, Sam, so it's not always the case, but I've often seen it be much more of an operational or tactical person hire. It's like, oh, I need someone just to do my systems work. I need someone to run analysis on all of this information that I have. I need someone to do campaign management. I would encourage people to think a little bit beyond and bring that strategy component in sooner versus later, because there's tremendous value. And that may probably go to the type of person you're hiring as well. But like, there is tremendous value in helping this, this person helping you think through how you should scale, right? Like, what does that look like? What are the things you need to keep in mind as you scale?

It's, it's super interesting. Lots going through my mind just around my personal experience, both with Zenefits and then with Brex. And at Zenefits, I pushed off hiring anyone in this function for too long. I didn't have an appreciation for it. This was also back in like 2013 was when I originally joined. I think the function was less maybe common within early stage startups around that time. And now, much like I have grown to have such an appreciation, I think that, that appreciation exists more broadly. And then based off of my experience at Zenefits, which was incredibly positive with sales operations, and ultimately revenue operations. Um, I, I pushed very early to invest in, um, making these hires and developing this function. I remember almost day one, like, one of the first hires I wanted to make— and, and, um, was explicit about this with Pedro Enrique— was somebody on the operations side. And so as we were hiring our first, like, set of sales reps, which was probably like 4 or 5, almost immediately I wanted to to sort of like pair those hires with also making a sales ops hire or revenue ops hire. Um, and this, this skill set— and this is where we're gonna go next— um, I, I think the skill set that oftentimes, uh, uh, is solved for in that hire is systems related. And it's because it's sort of like the immediate pain point that exists. The company is 2 to 8 sales reps, which is maybe the range with which I would suggest making this hire, anywhere between 2 and 8. And I think 2 and 8, there's a big delta there. If you're growing quickly, hire— and by growing quickly, I mean making lots of sales hires, I would invest in this earlier. If you are growing more slowly, you probably need less support on the strategy and operations side in the very early days. And so then, you know, I probably solved a bit for the systems experience. And I think what you're saying is maybe pair that with some of the like strategy experience. Go, go maybe one layer deeper there.

Yeah, absolutely. So I think the reason I would say that's exactly right, and I think it is like it's in the way you frame the question as well. Like there was, there was a lot of insight in that, Sam. So I'm going to pull out that thread a little bit as well, which is I think oftentimes it's like It's saying, what is the right level of growth? How do I think about scale, right? Is it 2 or 3 or 8, right? Like, what does a productive seller mean, right? Oftentimes having someone who is a partner in crime to like the sales leaders, because again, you mentioned this earlier, like if you think about this general profile of a sales leader, this is not something that they may have extensively worked in or they may have a lot of personal experience in, in terms of actually building functions like those or working in functions like those. Right. And so When you bring someone who's like a partner in crime and is like constantly asking you those questions, hey Sam, have you thought about this, right? Like, or have you thought, I know we think we need to hire, like, not like we need to grow fast to 8, but I don't know, I think you may want to think about these considerations. Or I see that you're not thinking about hiring fast, like have you thought about X, Y, and Z? And so having someone who has a slightly different skillset, right? Like that partnership is actually very critical. Right. And what you want early on is not just someone who will be like— because what you will get with the systems are like, thank you, Sam, I see what you want to do. Let me do it for you. Right. Versus someone who comes in and says, are you sure, Sam? Is that the path you want to take? Let's talk about what this means 2 years out, 3 years out. Right.

Yeah, it's really smart. I think the way that I— the way that I probably approached it or have thought about it in a way, was that the first operations hire would sort of be systems-oriented because that was sort of like the immediate pain point. Um, and oftentimes, like, the, the— those two skill sets, like being really sophisticated at systems and then being really good at like sort of like data analysis and strategy, don't necessarily pair in the same person. And so I probably indexed on the former, which is systems, uh, over strategy and not on the business partner side of things, but, and then solved for the business partner that you're describing, which is what you were for me, but when Brex was far more mature.

Yeah.

So like maybe the takeaway is have someone that can solve the system stuff, but is also senior enough and sort of business-oriented enough to be your partner in leading the organization versus just the system side of things?

So I think I would nuance that a little bit. I think, Sam, I think you may still decide that it is a systems person, right? But the point is that, like, definitely give it thought, be intentional about it. Like, don't, don't always go to the systems person first because that's how you saw someone else like like 5 other people do it. I think the reason to be intentional is each business is different, each business's needs are different, and you may not have the ability to invest in those resources, right? And so I think just being more intentional about it and seeing the different value that people can create, because you're absolutely right, it's a very rare skill set to be able to do both, right? And there are people who can, but it makes it rare, they're rarer to find, right? And then you're like, hey, do I wanna lead with that capability, or like the first person I don't wanna, I wanna hire is not the leader, right? And so there's like different, like there are different ways to go about it. The point is making sure that you are being intentional and thoughtful about that hire and seeing where you can get the most value.

Okay. Makes a lot of sense. Be deliberate about the skillset that you are hiring for. And then good segue to what is the like profile or profiles that you may want to then recruit from?

Yeah, so I've seen different, different things and I think we kind of covered a little bit. Then there are pros and cons to each, right? I think that you could start with a specific skill set depending on the need, which is it could be systems. But sometimes you could also hire someone who is very deep in data analytics, right? Like it is because you have a volume business, right? And what you see is a number of different data points coming in and you need to be able to translate that data into insights very quickly. What is this telling me? Right. And someone who has the capabilities not just to work through data, right, but able to surface the right insights for decision-making, because that is very important. And that, that, that's like a level beyond than just someone who can run like SQL queries, right? Like, so I think, so I think we, we, you want someone to go beyond. Like, I've seen people who like hires that are systems-oriented, more data analytics-oriented, and then depending on the type of companies, I've seen people who start with enablement, right? And they start with enablement because that is the biggest, like, it's because things are broken. People don't know what— it's just a very complex sale and there are lots of dots to be connected. And so I've seen that play out different ways. Um, that said, I think there is, uh, there is an argument to be made, and I'm actually seeing more and more of this, um, is where people start with a leader first, right? Which is, hey, the first person I want is that thought partner, and they can build out the team, right? But then it depends on the level of investment you're willing to make up front. But like that, like, what that person is able to then do is set the foundations in the right way, help think about the right people to hire, think about, and also help you think about what growth looks like, right? So that's why, like, again, depending on the need of the business, you could go either systems, data, deep enablement, or you could take a step back and say, I want someone who can grow with the company. Doesn't have to be someone super senior, but like has like that broad skill, broader generalist skill set, and they can dip their feet in, into the individuals. But like, I want that broad skill set.

Makes a lot of sense. So I think the takeaway that I'm leaving from these comments with is start by being very deliberate about two things.

Yep.

Are the, um, responsibilities that you want this person to own? Uh, do you want somebody that is, uh, uh, spiking on systems and very little around the sort of like data, uh, analysis, like quantitative side of things? Do you want somebody who is, um, more jack of all trades? Let's, um, frame it as that. So you start with the function that you are looking for this person to fulfill. Um, and then you also decide on the seniority. Do I want, um, just one, an individual contributor for now? Um, and as the business grows, this is likely somebody that we will top with a manager to then build out a team. Or do I want the leader to begin with? And then the profile is sort of a derivative of those decisions that you make going into the house.

Exactly right. Yeah.

Makes sense. Um, let's continue along. So, um, any, any sort of like mistakes or gotchas that you've seen startups make in making this hire or building out this function?

Hindsight is 20/20, right? So I think it's always, uh, so I, I want to caveat that, Sam, and not just because, um, Like people would be— I don't mean it as, oh yeah, okay. I like that. That's clearly obvious. But I think the reason I'm bringing that up is that this is based on what I have seen and what I have learned, right? Like I know as I continue to grow, I will learn more and there are other things that I myself would have done differently, right? So I'm just sharing my perspective here. I think one is something that you mentioned, like already is waiting too long to hire. This person. I think I have, like, oftentimes what happens is when certain things get embedded in the org, changing them becomes much harder, right? And also not just intensive, right? Resource intensive, right? So I think thinking through, like, having this part, like, I love the fact that as soon as you went to Brex, like, this was a conversation you had because you saw the value in it. Starting that conversation early doesn't mean it has to be like a second hire by any means, but it, it should be something that you're constantly thinking about in that, in that, in that intentionality bucket that we talked about and then being intentional about it, right? Like, who do we want to hire? Like, do we want to invest in the leader of the team that grows with us first or who's helped us scale first, has helped other companies scale and can help us do that first? Or do we want specific areas that we need more support on? Both in terms of the type of role and the seniority of the role. And then the final thing I think we also touched upon a little bit is I have seen people try to get the exact industry fit, right? They're like, I want someone who's worked in this industry for this type of product, serving this type of customer base, right? And I completely understand why that is an important aspect of the job description, what the expectations are. I think the one thing I would want to call out is the strongest people I have seen in this role, even people who eventually become, go deep in systems or enablement, are generalists, right? And the reason they're the strongest is for multiple reasons. They are able to connect the dots, right? Like that is a very, very important part of this function is like, they're not just looking at their piece. They're like, oh, do I, what are the dependencies? Right? Like, if I build a system, what else breaks? Right? Like, who needs to be involved? What am I not thinking about? Right? Like, those skills are very important, right? And I would solve for those, those core capabilities instead of solving for like what would be something that you look for and maybe other hires, right? Like for like if you're hiring, if you're looking to hire enterprise or in SaaS, like I totally get why you would hire a seller. Who's done that before, or if you want deep industry expertise, I can understand why you would hire a seller that, that goes deep, has deep industry expertise. But I think for this function, I think the functional capabilities, they will pick up everything else, right? Like they will be able— if you get a strong person.

It's so interesting. And I wouldn't have suspected this until working with you and your, like, I don't know, poster child or something like that as evidence of this coming from Google, which I think like I would have a bit of an allergic reaction to hiring a sales rep at Wrex from Google because of what you just described. Like, I don't know that it maps necessarily. And you came in and you were incredible. And then there's somebody else that comes to mind actually, and it's, it's Deep D. And I think Deep D was at like a big bank. I can't remember her exactly where, but one of the best people on on your team came from a big bank, and you really, I think, like, solved for this skill set versus, um, some of the, uh, directly applicable experience, uh, at, or experience at a directly applicable company, uh, maybe directly applicable experience at the bank, but, uh, uh, it was not a startup. Um, okay, let's keep going. So, uh, we have, I think, defined, uh, when to hire this person, some profiles to look for when making this hire, things to, to watch out for and maybe not solve for. Uh, one thing that comes up commonly is, uh, where this, this team or, or person should sit within the organization. And I think the options that I have seen— I've always almost required it, uh, to report to me, um, but— or, or to, to sit alongside me, however you want to frame it. Um, and, uh, but I think I've seen it live in finance and maybe like a broader sort of like biz ops or strategy ops function that has purview across the whole company? How do you think about that?

Yeah, I think it's a great question. So I have seen it sit in two parts. One is kind of a central org like finance, right? And then it can be— it can have a partnership with biz ops. It can be embedded like there's different combinations within that. And the reason why you see it in finance a lot is one is because it is there are a lot of similarities. And in terms of like also the teams that this team has to work with in addition to— and this is why you also want that cross-functional generalist, right? Like they have to work with FP&A, they have to work with accounting, right? Because you could have deal desk within this function. They have to work with different teams often within the CFO space. So I think there is just a lot of synergies there anyways. Right. So I think there's, there's There's definitely— I've seen this work within reporting to CFO at Guild. We report to the CFO. I think the, the other one is it's tied closer to the business, right? Which is COO/CRO function. I think the one thing, the two things I would solve for, right, in terms of both, just as to keep in mind, one is you want— you want the team to sit in a place where the leader, whenever you're ready to hire the leader, can be a peer to your functional leaders. That is a peer to your head of sales, peer to head of marketing, peer to head of customer success, peer to head of like BDR, if that's a separate organization, right? Like, or your sales architect team, right? Like, and the reason they should be peers is because you want them to, one, is be able to challenge them a little bit, right? Like you want that dynamic, you want that Yes, I am absolutely supporting and a champion of everything that you're doing, but I am going to try and influence you a little bit, right? And creating that peer relationship actually helps that a lot. So I think that's one thing to solve for. I think eventually when you build the team out, you may not stop that at sales ops, right? Like, but like when you have a revenue operations leader, that is probably where you want them to sit. And then if you think about like the other thing that I would solve for, and this is something to look out for when the team sits in like a function like the CFO function, which is a a little removed. Like, this team can only be successful if they're fully embedded with the function. It's okay if they sit organizationally somewhere else, but they have to be deeply embedded. And what that means is they're, they're like very much like working side by side with the sales team, side by side with the marketing team. Like, they should feel like they're a part of the team. Like, a test that I have is they're attending all their offsites and they're attending all their meetings and they're spending much more time with them than they're spending with their other peers on the broader, like, SOE team, right? And so I think that embedding is very, very critical because if that doesn't happen, then that this function cannot be successful.

Makes a ton of sense. What I'm, what I'm hearing, or at least taking away, is there are multiple options here. It sounds like within Guild, your function reports into the CFO, which is different from the way that we had it structured at Brex. Neither way is right or wrong. But what does need to remain consistent is the sort of embedding within the go-to-market team that you are partnering with. It makes a lot of sense. Let's, let's stick with early stage. One thing that came to mind as you were talking earlier around some of the like pitfalls that companies make here is waiting too long to make this hire. And so I'm just going to revisit that and then we're going to go more tactically into where the biggest opportunities for this team to have an immediate impact are. But one thing that came to mind, as you said that, was, you know, I referenced earlier sales ops, revenue ops. It was less of a thing when I started in sales back in 2008. I'm aging myself a bit here. And EchoSign, we were like, gosh, 100 to 150 employees or thereabouts when Adobe acquired us. And we didn't have anyone in sales ops. We had Brendan, who was our VP of sales, and we had— I think I was a manager at the time and, you know, maybe a couple other managers and teams. And we really ran the operations within the department ourselves. And then within Adobe, we were sort of assigned a sales ops person and the experience was like not great. And I remember when I went to Zenefits, this was again back in 2013, Um, when I went to Zenefits, uh, I was a bit allergic to investing in this function based off of, one, it was like a little bit less common and also not the most positive experience. And I remember I just kept talking to other sales leaders, trying to learn from them who had done this before. This is my first time, and one consistent theme came out of every conversation. We were growing very quickly, um, and one consistent theme came out of every conversation. It was like, if you're growing this fast, you have to invest in what Sales ops at the time. And I, you know, I would be like, look, I've seen that and I don't need any of that in those conversations. But eventually I was like, okay, we should probably do this. And that's where I very quickly gained some appreciation. We may have been something like 20 sales reps at the time we made our first hire. But that's when, you know, based off of that incredibly positive experience, I came to Brex and did exactly what you described, Charisma, which was like almost through the interview process, where, you know, maybe there's a question that's something like, what do you need in order to be successful? The first thing that would come to mind would be, I need a really strong operations counterpart or counterparts. And so, you know, just reinforcing a bit for founders and other sales leaders out there, having the right people in place within this function can just have an impact that is truly game-changing. With With that in mind, let's stick to these early days that we've been talking about. And if you join a company as the first revenue operations leader, do you see any consistency around— or sales ops, whatever— do you see any consistency around where the biggest opportunities to make an impact on the business lie?

Yeah, absolutely. So I think I will try and categorize it into 3 or 4 buckets, Sam, and knowing that these are like— this is a more generic answer, right? Like, this is what I would expect. But that said, I can imagine as this hire comes in and there may be a burning need for a specific problem to solve or a challenge to overcome, then that probably takes precedence. So the 4 areas I would call out is one is is building a strong analytical foundation. And what I mean by that is it's very important to lay the groundwork for these are the metrics that we should look at. These are the metrics that indicate success, both in terms of input and output metrics. And also things like this is what good looks like. What does it mean to be a productive seller? What does it mean to be— what should our velocity look like? What should our win rate be? Like getting into that rhythm, like looking at the metrics we want to measure and then starting to define what what it looks like. I think that's, that's an important part. And then slow— this evolves into what are the metrics I need, insights I need to surface for decision making, right? That's kind of as a level 2 in that. The second, I think we talked a little bit about already, is around building the foundational processes, which is sales methodology. How do we work with our partner teams, right? What are the roles and responsibilities between— if you have sales and solution architects, or sales and BDR, SDRs, BDRs, if you have sales and like, where does transition happen between sales and post-sales, right? Like all of those thinking about R&R and thinking about sales methodology, thinking about all of those processes that will help the business run. I think the third is, this is the systems piece, which is around, hey, as I develop, I think it's, it's also important to make sure the timing of the sequencing of this is right in a way. Oftentimes, what you want to do is make sure you have the right process before you put it in the system, right? Like you need to define the sales methodology before you put it in the system. You need to define like, and so what you will likely do is you will do a few revs outside of a system before we actually put it into a tool, right? And that is actually good practice, right? So if you see people are saying, hey, let's just continue to work out of Google Sheets or whatever tool that you use right now, and then we'll see if this sits and then I'm going to put it in the system. I think that works, right? Like it's okay for, for a little bit of time to get it right in a place and then put it in the system because then that is where you feel like, yes, I— it makes sense for me to land here. And then the final is my favorite thing, of course, which is like early markers if you can on go-to-market strategy, which is like what is addressable? And what segments should we prioritize? Why? What should our go-to-market approach be? How should we hire against it? So and so.

Awesome. Super helpful. I think we'll revisit maybe, maybe the last one in the form of like telling some stories around things that we have seen revenue operations do and just have a massive impact on the business. Before we get there, let's just quickly talk about scaling and how you think about scaling this organization alongside the rest of the business that is growing. Growing. How do you think about the right number of people the revenue operations team should have? Is it correlated to sales headcount, headcount in the revenue operations, or broadly? What is this sort of like best practice there?

Yeah, I think this is, this is a really great question. And this is especially hard to do, especially in a scaling organization. So let me walk you through what I mean. I've seen people struggle with it. There are ratios, absolutely, there are ratios, there are ratios that I've seen would say it is anywhere from 5 to 7 to 10% of the teams in scope, right? So you don't want a sales ops team that is bigger than like 10% of your sales team. Like similarly, if you think of revenue ops, you think about functions more broadly because it includes different, not just sales, like it includes marketing and CS and so on and so forth. So there are absolutely benchmarks, right? But you have to be careful about using those benchmarks for two reasons, especially when you're scaling a team. You may have, imagine you have like 6 different teams already, right? And you just have 1 or 2 people in each team. Doesn't mean you can only do like 1 person in revenue ops because it'll be very hard because some of the processes still exist. Just because you have 3 sellers doesn't mean you don't need an incentive plan or territories, or doesn't mean that you don't need an actual— like, just because you have like 2 marketing people doesn't mean you don't need to figure out top of funnel, right? Like, you still need to do all of those things. And so I think it helps the ratios are really good benchmarks to keep in mind, but I would layer it on with kind of a jobs-to-be-done framework as well, where you're like, hey, what are the things that I need accomplished and what is the right number of resources to help me get there, right? And so that's a little bit of a bottom-up build. So think about a jobs-to-be-done bottom-up build with a top-down, does it feel right in terms of ratios is the approach I would take.

Got it, makes sense. And maybe what comes to mind is a couple things. One, uh, is around structuring the, the team. I think the way that you did it at Brex was you were my business partner. We referenced Deep D. She was, um, Ashley Kelly, who was our VP of SDR. She was Ashley's business partner. And we had Naomi, who was, uh, our VP of channel sales. Kurt, his business partner. And so you sort of structured the team around, um this, this like business partner concept where people owned a lot of the, the different sort of like functions, I would say, maybe except for systems, which seemed to be centralized. Anyway, I don't mean to answer the question for you, but how do you think about, um, structuring this team? And then maybe, um, something that also comes to mind that is slightly related to scaling, but like just in terms of measuring the impact or how to determine success of, uh, people or this function broadly, um, and, and how— because it's like It's unlike sales, it is less objective. So would love your thoughts on both those things.

Totally. So let me start with the first one. So first I would say thank you for answering part of my question.

Okay.

So I think it's exactly like my ideal structure and I have like tested it like 3 times. And so I feel like it's resonated 3 times in actually different size organizations, right? Like, so it feels a little sturdy. So that said, I'm positive I will learn and I will grow and this may evolve. But like one of the things that like the approach that I take is yes, definitely business partner that tied to the functions, right? So there is generally what I see is a strategy and ops person for sales, BDR, for customer success, for channel, right? For marketing, right? Like, so you sort of see those functional ties and these are your very strong generalists, right? Generalists. These are the thought partners. They can— they're very strong operators, right? Like the way I would hire this person is very strong operators that are also strategic, right? Because what you cannot compromise on here is your basic operational foundation, right? So they are strong analytical people. They are also strong at capturing insights and surfacing the right things. They also understand how to set incentive plans, thinking about quotas or thinking about the funnel, right? Like they're, they're good with like the operations piece, but they think about problems strategically, right? So they're not just like solving it, but they're thinking long term. They're being good influencers. They're, they're raising the right questions, right? So that's the business partner profile. And then that said, there are certain functions that I feel like are specialists, right? So you have the business partner journalist, and then you have the specialist, which is exactly what you talked about, like a systems role. And the reason you have generalists in here is because of the type of profile you want to hire. And they're just like, they're specialists. So why, why wouldn't you scale that right across the different functions? And by definition, systems should connect, right? Like you don't want someone just looking at sales systems and someone just looking at marketing systems and just looking at customer success systems. You want them to talk to each other and all the more reason it should be one team, right? And similarly, for enablement as a type of skill set, and you want them to come together, um, and, and making sure that they're sharing best practices, right? It is one team that does enablement, onboarding, or continuous education for all of those different functions. So there are, there are some that form like the specialist layer.

Makes a lot of sense. So, um, the way that you have designed it, uh, and it worked at Brex was this concept of sort of like business partner for each of the leaders that is focused largely on data analysis and strategy and improving sort of like outcomes with whatever the mandate within that team would be. And then systems and enablement are centralized because of the skill set.

Yes.

No, go ahead.

No, I think the only thing I was going to add is that GIL is a little different because it's a marketplace. Right? So what we've also centralized is because you have different types of customers, right? Like you can also centralize Deal Desk. Similar profile, right? Like, but that doesn't always occur in businesses, so.

And then second part of the question was around sort of like measuring the impact or success of this team, which is seemingly a bit more subjective, although there are a lot of objective data points that we could point to, but like, less clear maybe than something like a sales team?

It will be, right? And that is the nature of the role, right? And that is why what is very, very important for this team is very clear objectives and what success looks like, right? So one could say, hey, this person is truly influencing, like it's hard to measure, like, is this person a good influencer, right? Like, because the point of influencing is that it feels like you came to the decision together, right? That's what influence is. Right. And so oftentimes it becomes hard to say, oh, look, check the box, success. Right. And which is why for this team, especially having very clear objectives, say I want to have by the end of this quarter a clear forecasting process. I want to have by the end of this quarter, like our sales methodology defined. Right. And then like making sure that we are keeping to those objectives. Right. I think that would be the way I would approach it. I think the one thing and I was debating this with with my manager just now, who is the CFO of Guild. And we were talking about it and we were like, how do we balance making sure that teams are giving it their all and like they're doing that, like they're achieving that objective, but also instilling an atmosphere of test and learn, especially in the startup environment, right? Like you want people to be able to be a little bit more nimble and say, I don't have to wait for the perfect answer. I have a good answer. I'm gonna run with this. I'm gonna learn, and then I'm gonna iterate. I think that is something that is harder to do, especially for teams like this, is like you want them to be able to accomplish things and do it well, but at the same time, be open to testing and learning and evolving. So I think that is something even I'm trying to figure out, Sam, how I incorporate that in my objectives, but that is something to continue to work on. To think about.

Okay, makes sense. Let's end on maybe my favorite, uh, topic that we, we had planned to discuss today, which is, um, just around— I can think of countless examples of things you and your team, um, are or were responsible for that changed the growth trajectory of Brex. And I'll talk about, um, in the interest of time, maybe just one of them. But are there any stories that come to mind of things that you or your team have done that have been transformational for a business that may apply to listeners and their businesses. Um, and again, sort of like going back to the idea of sort of like tactically coming away with something that maybe, you know, this worked for Charisma and Sam in my story, maybe we should try it in our business.

Totally. And I'll give you some very quick examples without getting into the actual details of which company, because that's where a lot of like context may not be relevant. So there was, uh, like our team built a very thoughtful incentive plan, right? That we are very clear, these are the behaviors we want to change. Incentives drive behaviors, right? And we created an incentive plan to change those behaviors, and we were able to see that change, right? That helped us get to actual growth and the direction the company wanted to go. That was very fulfilling because that is actually— you see the impact, right? May not be what it means is more productive sellers or whatever it is like, but of course the sellers are the ones that got more productive. But this, that what the team did helped influence that significantly.

Yeah, what comes to mind— and sorry to interrupt because I know you have a couple others— is, is at Brex, when we shifted the comp plan for SDR from, um, like opportunities created to revenue generated, and the output of that was a lot more revenue. Um, and, and so maybe that's what you're referring to, but I think that's—

yes, like, I, I'm generally hesitant to like call out specific company names as well Sam, you can with Brex, right? Because it's like, it's also being a little bit more thoughtful about the actual companies themselves and if they'd be okay. Then I think this, I can say for Google Cloud, we created a very clear named account strategy and a segment, right? So we created the named account segment, we created the strategy that goes along with it, and that saw significant uptake and penetration in that segment. Segment, right? And so it is not just like saying, hey, what does that strategy look like? It is, what does that segment look like? What should be included? But also, what should we do different for them so that we drive the result that we were trying to drive? Another one that we're working through within Guild actually is we're saying, let's build a tiered service model for our customer success team. That helps us not just think about how our customer success team prioritizes their time, right? And where they focus, but also other teams. It's like creating a common language across Guild where you say, if this partner is this tier, what does it mean in terms of not just this, what customer success is able to do for them, right? But other teams also do for them. So it's creating that common language, which can be incredibly helpful and catalytic. Terrifying for folks. And then again, a more recent example with Gil is with— we're doing this top of funnel work where we've looked at velocity, we've looked at conversion rates in our funnel, and then we say, if I have to achieve my growth aspirations for like 2 years out, 3 years out, 4 years out, what do I— because of our long sales cycles, what do I need to do now in terms of top of funnel so that I can drive that, right, in the future. Because those things won't drive you in your target, right? Like these are future year targets. So I think making sure you have the right data and like, and just like you're using data to get to the right behaviors you wanna drive and then using that to set targets is another cool example.

Makes sense. All really great examples. I'll quickly tell one. We've probably gone long over the, the time that we normally go. You and I used to joke that we both talk a lot, and so no surprise there.

There we go. Yes.

And, uh, uh, okay, so I remember, um, back at Brex, we were noticing that there's just a lot of variance in data around, um, deal sizes, and there was a big discrepancy between the average opportunity size that an AE was generating throughout outbound and the average opportunity size that an SDR was generating from outbound. And then a lot of variance again at like the individual contributor level where certain individuals were creating much larger opportunities than others. Um, and it's because like all of the activity that people were doing was, um, like at their own discretion, maybe some like loose guidance around, you know, these are the types of companies that we think are going to spend a lot of money. Um, Um, but when you were an SDR or an AE, you turned your computer on in the morning, like, what you did that day was ultimately up to you. Like, you got to pick which accounts you add to the database, which contacts you go after in those accounts. Um, and, uh, because, like, you know, again, some loose direction around those things, but because of that, we, we sort of like led to this outcome that was a wide variance in performance and a wide variance in things like opportunity size. And so, um, Trish, I know you made a dedicated hire ultimately to own this, but, um, we, we put in place like a very sophisticated lead scoring and activity, uh, sort of, um, uh, predicting or activity recommending, um, system where we knew exactly, uh, or we knew relatively close to what, uh, a company would generate in terms of revenue. And so if you're an SDR, you opened up your computer that day, you actually saw within your account territory, these are the accounts you should go after today because they're going to generate the most revenue. And then within the account, you would see these are the contacts you should go after within this account because these con— I think we called it a hustle score— these contacts have not been reached out to in the longest period of time, and and/or this persona has the highest probability of converting. Because, you know, it was like maybe a CFO versus a controller and those convert at different levels. And then you even extrapolate it out further because this is a controller, use this message when you reach out to this person. And so we just really automated, or you, I suppose, really automated like so much of the subjectivity that led to this like variance in deal sizes. And I think the result of it was a few-fold. People were far more effective and efficient, but I think the like biggest data point that we could point to was something like a 3x increase in the average opportunity size because people were going after the opportunities that generated the most revenue for the business in a very automated way versus this sort of like subjective, I'm going to reach out to these e-commerce businesses today because e-commerce Tends to generate a lot of revenue, something like that. Um, that is a, a story that I think back on, and there were, as I mentioned, many others. But just the type of impact that revenue operations can have, and you can imagine if all other things remain consistent and your deal size or opportunity size 3Xs— um, it took us for a few months to do this— um, the outcome of that is you 3X sales. Um, again, if everything else remains consistent. Um, we, we did all sorts of things like that, but that was one that had a big impact, and I thought maybe A good one to end on. So, Charisma, thank you for taking the time to join me. It's lovely to see you as, um, always. I miss you. Um, to all of the listeners, thank you for, uh, listening to this latest episode, and we will see you soon.