From Sales Ops To GM With Gainsight's Ryan Toben

Sean Lane: Hey, everyone. Welcome to Operations, the show where we look under the hood of companies in hyper- growth. My name is Sean Lane. We've spent the majority of the time on this show looking at the work of operators, what they've built, how they've built it, and how their work has powered the companies that they are at through hyper- growth. Where we haven't spent enough time though, is on the career development of the operators themselves. How did they get themselves into a position to make that impact? What are the different paths and options available to ops folks? Today, we're going to change that by looking at a specific role that could be a future landing spot for people who are in ops today, the GM. And our guest today is someone who started their career in ops, and then leveraged that experience to make the jump into sales leadership, and ultimately to become the GM at one of the most notable hyper- growth companies out there today. Our guest today is Ryan Toben, the senior vice president and GM of EMEA for Gainsight. If you aren't familiar, Gainsight is the leading customer success platform. They made headlines recently when they took on a majority investment from Vista Equity Partners that valued the company at$1. 1 billion. I should also point out that Ryan and I recorded this conversation prior to the Vista announcement. Now, Ryan spent his first three and a half years at Gainsight working state side before moving to London in February of 2020 to lead their European office as the GM. In our conversation, we're going to talk about what the hell a GM does, how Ryan leverages his ops experience in his work today, and why it's so hard to shake the imposter syndrome of having never carried a bag in sales. Let's start with this role of the general manager or the GM itself. I asked Ryan to break down for me the scope of his job and the different responsibilities he thinks about every day.

Ryan Toben: Functionally, that role is somewhat easier to explain. I am responsible for our sales marketing and post- sales, so customer success and services for the region. We have a satellite office in London, and then we also have, because Gainsight's got... about half our company's in India, we also have a number of teammates that are in India. So functionally, that's my role. I report into CEO for this part of the business, and then work super closely with the cross- functional leaders of the head of customer success, head of sales, head of marketing to make sure that we're all aligned. More practically on what the function is, it's a good question. And actually when I started the role, the previous GM, my predecessor, a guy by the name of Dan Steinman, who literally wrote the book on customer success and moved to Europe to build the movement around customer success and then Gainsight with it, he was the GM and I was coming over and we did this big QDR for the team. And I said to the team," I honestly don't know what I'm supposed to do as a GM. I know what Dan did, which was get on stage and evangelize what we're doing, but that's not my background and it's not what I've been asked to do." So I opened up with," I've been leading ops and sales for the most part. I know that's part of the job, it's all a job." So since then, that was in February, also in a pre COVID world, so a lot has changed. But since-

Sean Lane: Yeah, not getting up on stage anymore.

Ryan Toben: Yeah, exactly. Not on stage. Exactly. I have come in with, at least for me what the GM role is, and it's in three parts. And this is how I explained it to the team at our mid- year Zoom offsite. The first is representing the team internally and externally. So we call it gravity, but senior executive meetings, cross- functionally if I need to push for needs and get head count or budget or work with engineering or whatever it is internally, or speak at one of our all hands, that's a big part, making sure that as a satellite office in particular there's a definite concern that people are forgetting about us. So that's one, and then the external side also, which is more reactive external stuff, talking to a VC about their port codes, talking on a podcast, doing a presentation, meeting a customer, meeting a prospect, whatever the team asks me to do in a more reactive manner as things are going on. The second is backing up the leaders on my team, which is the gentleman who runs sales, the woman who runs marketing and the gentleman who runs customer success, and just covering for them when they need to focus on other things. So for our customer success leader, he's got a number of initiatives this quarter. We invest heavily in our partner ecosystem to implement Gainsight. So that does fall in his realm because they're post- sales, but I am taking a decent amount of that now because we have other priorities that he wants to focus on. So how do I back him up? And then the last one is an attempt to look more than six months out. And this is where I'm more proactive. So what am I pushing on the team? What am I asking people to do? What am I focusing my time on? So one thing for Gainsight as an example is managed service providers are resellers managed service providers, organizations that will sell software or sell hardware and then actually manage it for the end customer. They have been on a path to adopt the concept of customer success. So they pose a potential growth opportunity for Gainsight, but we're not going to hit or miss our number this quarter or next quarter based on them. We do have to have small wins and small progressions with them in order to build on that in Q1 to Q3 next year. So while the team doesn't have the capacity to spend as much time on them, today I am trying to push the little things that aren't going to put a lot of dollars in people's pockets this quarter, but hopefully will in the future. So that's how I think of the third part.

Sean Lane: Okay. Let's recap Ryan's three areas of focus as the GM. Number one, he represents his team, specifically the AMEA group internally and externally. Number two, he provides support for the go- to market leaders within his team for any specific initiatives that they are working on. And number three, he's proactively and strategically looking more than six months out at the big rocks and opportunities for his part of the business. So with this scope in mind, the next question is how exactly does one become a GM? Ryan was at Gainsight for three and a half years before moving into this role. So for folks like you or me wondering about whether a GM role might make sense for us in our career path, I want to understand how a role model like Ryan went about that journey.

Ryan Toben: So I was a consultant and I wasn't in tech. I was consulting customer strategy consulting and didn't like it. So I applied for a bunch of jobs, ended up at SuccessFactors, running what was pricing strategy, which coincidentally, or not coincidentally but it happened to sit under operations, sales ops, which I have since learned is not all that usual, but that's how it worked there. I had no idea what sales ops was. I didn't know what frigging sales wise basically at the time. And I wasn't looking for tech specifically, so I fell into this role, but I liked the role that I was doing. And that opened my world to the sales side of things, the operations side of things, the tech side of things. And I really liked it and I really liked the numbers and the strategy side of what I was doing and the cultural aspect of what sales does and then the comradery. And then tech in general was interesting because it's this growing world, particularly SaaS. So I got my path there, and as I was doing the added SuccessFactors, I have a very mean for moment, I guess, where it's the end of a quarter and I'm late in my desk, helping on some deals, helping with pricing deals desk stuff on some big deals that were coming through. I'm sitting right next to this woman by the name of Marjorie Toucas, who at the time ran a SMB for SuccessFactors. And I'm coaching this rep on a deal in terms of how to work the pricing, who to talk to, here's how you think about it. And afterwards, she was like," You sound like a sales manager." And that was the first time I ever thought about," Is sales the right path?" I grew up on the East coast and went to prep school and went to get my MBA and sales was a dirty thing. It wasn't for people who had gone to business school, and started really changing my mind. But I really liked ops, I really liked what I was doing. Things were going well, so I wasn't really pursuing it. I also worked in big enterprise sales at the time. So these guys who'd be doing it, these guys have been doing this for so long and on the road all the time and these huge deal cycles. And it didn't seem like it was a natural transition. So then I ended up going to Mixpanel and when I was at Mixpanel it was the first time I really got into SMB and fast deal cycles and data and the funnel and enabling lots of reps and all of these things that really do speak well to people who have an operations mindset and who like that part of the business. So that's where I started to think to myself that I think I can do this. And frankly, all these things that I've been trying to get sales leaders and sales reps to do as this influencer, hopefully I can with more control, get the chance to do that. So that's what sparked my interest in sales. So I had the opportunity to be acting CRO for a little bit at Mixpanel, although that was always going to be a temporary role. And so after that, I started looking for a sales leader role. Came to find out that nobody really wanted to hire me for a sales leader role because I was an ops guy, and the few people who were talking to me, they really just weren't in companies that I was super interested in talking to. So ended going to Gainsight, met Nick and I told him what I wanted to do. And he told me what he wanted, which was somebody to build this rev ops concept, working with marketing and sales. And then in the future, if things go well he would champion me to take that step that I wanted to take. And that's how it worked out. I built out rev ops at Gainsight. It did go well. I slowly got more responsibility and then slowly they started putting SMB and things under me. And then eventually, I really just made the jump over to the sales organization. And truth be told, sometimes I ask myself which one I like more because I definitely like numbers. I definitely like understand funnel and what's going on and the more numbers, the better because it can help you see the trends and that kind of thing. But frankly, I worried that if I stayed in ops, I would be capped at a VP of ops and maybe I'd find someone who'd promote me to COO eventually, but would it be the role I wanted or how fast would that be? And I felt like if I went into sales, owning that number and being the person responsible versus the person that was advising the person responsible was going to be the more fruitful path over the course of my career. So that's what my mentality was.

Sean Lane: That's so interesting. I've got a bunch of follow up questions for you, but one of the things that really resonates to me what you're saying, and it's really funny how similar you are, we just had a recent guest Emmanuelle Skala, who's the senior vice president of customer success at Toast. And she also had this operations to sales to CS path. And one of the things she said that really stuck out with me, and I think maybe you would identify with this as well is she's like," I get just as much of a thrill behind a spreadsheet and looking at numbers as I do in a customer facing situation." And basically, that juxtaposition of those two things side- by- side basically has driven her to try to do a little bit of both in her career. And I feel like that's part of the transition that you've been making too. I'm curious, when you were getting Nick and Gainsight to make that bet, and you were building out rev ops and ultimately made the jump into sales later on at Gainsight, a lot of times you'll hear people say," Well, you can't be a sales leader if you haven't carried a bag, if you haven't held a quota on your own in the past." And I'm curious, how much of that was in the back of your mind as you were making this jump, and if you had this weird imposter syndrome, as you're trying to make that transition internally at Gainsight, and ultimately lead salespeople?

Ryan Toben: So a couple of things there. I think that when I am behind a spreadsheet and I find a trend that I think can actually be meaningful, I agree, I get as much satisfaction and excitement out of that as I do leading a meeting being like," Oh, we just crushed it." And I have tried to sell to Emmanuelle, so I wish I knew that we had that crosstalk because I would have brought that up when we were meeting. But that's a different story.

Sean Lane: I got you a foot in the door, though.

Ryan Toben: Fair enough. The idea that I have never carried a bag is very much prominent in my mind. And at Gainsight I've gotten over it because frankly, I leaned heavily into that. Actually, when I first took the role... Oh no, I take that back. So my last role at Gainsight, before I went to the GM is I ran PX, which is our product experience tool. It's an acquired company. And it was a big focus area, big growth area, first acquisition for Gainsight. So when they were deciding to make the offer to me to run that, one of our board members who is the sales board member, he is the guy and he's great, he was all over me about," Are you the right person because you've never carried a bag? And I need someone who's in the trenches and selling and doing these things." Luckily, Nick and at the time my boss, Brian said," Yes, he is," but it was not the most pleasant of conversations crosstalk. But as part of that, I would actually amuse him and say, " Okay, what would you do? What deals would you be on?" And I tried to bring myself to as many conversations as possible with customers where I can add something. And for me, and what I would guess for a lot of strategy and ops people, for me that's doing disco. And I learned that pretty early on. Pretty broad business background. We're selling generally to customer success. I understand customer success in sales. And we're selling to SaaS. I understand SaaS. So I know that if I show up in a intro call, a disco call, I can understand their business substantially better than the rep can, substantially better probably than the first level manager can. So I know that I can add something, and then be there with the rep to be like," I'm adding value. I'm not just the executive you have to bring to a call." So that's really what I try to lean into. And then after I did that a bunch and pushed away from my natural tendency, which is to just look at the numbers into how do I understand these customers and deals, that became something that doesn't really come up anymore, not at Gainsight. It does however, occasionally if I take a recruiter call or something like that, that's where it does come up still in terms of," Well, you've been doing this, you've been in parts of sales for the last three years, but you didn't carry a bag, you do this." And my talk track around that has always been," This is my background. This is my benefits. These are my drawbacks. You're either going to be bought in or not. If you're not, I can't convince you otherwise," which sucks but I'd rather lean into it and lean into the benefits versus just focus on the negatives.

Sean Lane: I love the way that Ryan leans into his background and owns the experiences that he does bring to the table, as opposed to being put into some box as a result of having never carried a bag. And to be honest, I think that the tours of duty he has done in all of those different roles have set him up for the unique value that he's able to bring to those deals and bring to the discovery that he's talking about. I see the same thing internally at Drift all the time. I'll jump on a call with one of our prospects or one of our customers. If they're talking to our team about how to best implement Drift or how to instrument and measure the impact of Drift, because I do that for our own company every single day. So my conversations with ops leaders within our customers are the types of conversations that frankly, I'm uniquely positioned to have. The difference now, of course for Ryan is that as the GM, he owns the whole thing, not just ops. And we've talked about how Ryan saw his ops background as an asset, but he mentioned that making this transition from ops to sales to GM was also a transition from an influence role to an ownership role. So I was curious now, looking back a few years removed from being only in ops, has his perspective of operations teams or the relationships between ops and sales, has that perspective changed?

Ryan Toben: So there's a couple of areas. On one side I think that the big difference is there's the human aspect of what's going on in a deal or with a rep or with a team that when you're having all those one- on- ones and you're going to these calls together and you're living some of these deals, you focus on first. And when you're in ops and you have every rep and every manager to think about, you know that that exists and you have to think that way, but it's also really hard because you're also trying to get what you need to get done. So things like how you think about comp or a spiff. Spiffs I think of very differently than I did when I was... because there are certain spiffs that on paper, could be super expensive. So then when you fight in ops with finance, you get it approved, you're so excited and you launch it and you're like," There is two parts in it that it's like, nobody's going to do this." And it's super easy to see because you've worked with the reps and you're like," They're not going to do this part. It's not going to happen and it's a lot of work to do that part." You want it there because you want to make sure that there's not gaming of the system or something like that, but it's a much bigger hurdle than you appreciate. So there are certain things that inaudible versus maybe spreadsheets that I think I see. Another part, which when I was at SuccessFactors is at a time I was running ops there and a guy who ran North America for sales for us, a guy by the name of Dave Dyer, he had a big organization. He was much more senior than I was. I was the head of ops that he had hundreds of people and salespeople and inaudible in his organization, we're at his offsite and we're doing planning for the following year. And he said to me, pulled me aside and he was pushing for a dedicated sales ops person for him. I was like," Why would you want to do that?" And he wanted me to report to him. He was like," I want out of your organization. I want a report." And I was like," Why? That's efficient. We're doing all these things." And he said to me, he's like," I don't feel like a customer of the ops team." And honestly at the time I was like,"What are you talking about? All these things that we do for you, we build this, we build that." But then going to a similar role that he had, not as big a role as he had because we're not as big a company, similar role, and thinking about his boss there who was the equivalent, he was president. And for me, it's the CEO because we don't have a CRO at the moment. And I frequently now think the same as here we did, which is, there are things that I want to get done that I need ops help for and I'm just not a priority because I'm only a part of the business and everything is about what the CEO, or if we have a CRO, CRO or CMO want to do across the company versus this idea of my area. And I imagine it only gets worse if you're just running the East or if you're running the Northeast, these smaller things, the smaller analyses that sometimes I want to do that I can not get done. And I feel now, and granted I'm biased crosstalk for myself, but I, a lot of times feel like this small analysis that I want to do that I need some time from you to do is actually going to move the needle more than the big stuff that the CEO just came up with, because his is an idea and who knows if it'll work? Mine is a tactical," This is what we're going to try to do right now." So that it was one area that's been pretty different for me, this feeling where I always thought I treated everybody great as an ops leader and now that I'm on the other side... and by the way, I love our ops team. They're great. So this isn't a matter of them, it's just a perspective on all these things. I will also say though, just one other point to give the other side, sometimes Caitlin, who runs ops for us, Caitlin Quinlan, she will push on a forecast call on one of our deals. And I'm so far into this deal that I get defensive and then I have to take a step back and I'm like," Man, she is right. This is the kind of thing I would have done when I ran ops." But you get close to the rep, you get close to the deal, and all of a sudden you start to make excuses. So that has been somewhere where it's really helped me. And I try to go back to my ops perspective.

Sean Lane: Just the fact that Ryan can actually take a step back and see both sides of these relationships is to me, a benefit of his perspective. And I've said on this show before that I do think that if you're a sales leader or a CS leader or any type of manager, you should put your team first and you should be looking out for your team's best interest. And then on top of that, we as operators will often need to come in to bring a more objective lens to the same problems or challenges, and make the best decision or best prioritization call that we can. But Ryan's story should also encourage us to be constantly checking in with our internal customers to make sure they actually do feel like customers, or that the work that we're doing for them is actually what they think will move the needle, because if they don't feel that way, or if they don't feel like they are truly customers, then why are we here? What are we doing? Let's get more concrete. Let's look at a specific example from Ryan's world, fighting for budget. Imagine a scenario where one of those same leaders that Ryan is talking about, needs to fight for budget for their team. How can they best do that? And how does someone with Ryan's experience in both ops and sales, how does he think about these conversations?

Ryan Toben: So this is something where I think that having the opportunity to be in ops and lead ops has been immensely helpful for me, especially now in having multiple functions and trying to wrap it all under these single goals. For Gainsight, just like many companies, we are kicking off planning right now. I'm currently in the middle of writing my paper for the next two year plan for EMEA. And we're basically going to go through there's about eight papers on different things that are being written for planning. We do a draft session, we talk about it and strategize, and everything two weeks later, we finalize. But then as part of this, these are big picture concepts that we're trying to do, goals. And then to the side of that FP& A the rev ops team are building out the models and the plans and how does all that work? And then these papers are meant to be the defense for the different areas that the company's going to invest in or not invest in as the case may be.

Sean Lane: When you say paper is this literally pros? This is a report or is this bullet points? What does this look like?

Ryan Toben: So it's a paper. It's what are we doing? Why are we doing it? How are we going to do it? What are the risks? And there's a lot of bullet points. It's not creative non- fiction or anything, but it's in a Google Word doc, or however you say it. And there's charts in the back that I want to show, interestingly enough, for me, there's actually a lot of charts. For some of the other people writing them there's no charts because it's just how we think about things differently. And then some standardization. So you can have a one pager that summarizes it. But the idea is everybody needs to read everybody else's papers, that's on the exact staff. So anyways, so we go through this, my philosophy, and this is both with my team in Europe, but then also to the leadership is generally speaking, the leadership team, I am aware, knows that we in the field in Europe know more about what we need than they do. And that idea because I've been in ops and I've been in planning, is very tangible to me. I don't think that a lot of people in my shoes who haven't had that experience in planning appreciate that. So what they're really looking for from my perspective is some goals they can measure us by, both in that we have this concept of this paired metric. So if I have an AR target two years out, my paired metric is my CAC ratio. So yes, I can grow, but I can't spend too much. I can spend a certain amount. What do we agree on? So circle around that. Logically I need it to be reasonable so that people buy into," Oh, these are reasonable things," in terms of we're going to try to gro, and then here are the specific asks that I'm planning. And I have to have conviction around daring to move the needle because of this, but I'll stand on my CAC ratio, which makes sense to my ARR. And here it is all in a bundle. And the rest of it is really just, am I holding up my part of the bargain? I'm asking for resources, am I committing to delivering something? Even today, I had a conversation with me sales leader here. We were talking about heads that we need to hire in order to hit our numbers next year. And he's worried about ramp time. And we have traditionally in Europe had slower ramp time than in the US. I think part of that's probably the distributing model. We're younger, we're further behind in the maturity of CS, lots of different reasons. But I basically said to him, I'm like,"Listen, I appreciate that." And this is not as clear as I'm about to say it because we argued about it for a while, but," I appreciate your concern and that this has been how it's been in Europe for the last two years, but that is worse than it is in the US and I cannot walk into our exec staff meeting and tell them that we're going to be a lot worse at this thing, at that ramping than everybody else. That needs to be something you and I fix. I can not bring that up." And he's like," Fair enough. We'll fix it." He's like," That's a concern I have." And so it was productive, but it goes two ways. I with him had to be like," I think that I've seen other people bring all of their problems to the executive staff when planning, and then it gets noisy and it's hard to buy into what they're saying," versus some of the problems that specifically the exec team can help with. And then the rest of your problems, you're the leader, you got to deal with it.

Sean Lane: Right. And I'm true as you talk about writing your paper and you have to go back to the executive team, or you're comparing yourself to these other business units, how much of that revenue target and the paired metric that you're talking about are things that you are arriving at and it's bottoms up versus the company says from a top down perspective, this is the revenue target. This is the paired metric. Go figure out how to get there?

Ryan Toben: So Nick gave me a first metric, which I elected to not use because my view was, and I asked him first, I didn't just ignore him. I was like," Is this okay?" Because I think that your first metric is so above and beyond what I think is reasonable that it'll change how we need to plan. We'll have to do something much bigger and that's a much bigger risk, a much bigger cost is that what we want to do. So in that case, I got to choose some, but I will go into this first one and they're part of the first round it is I don't think I'm sandbagging, but if they think I'm sandbagging, this is their opportunity to tell me they think I'm sandbagging, and," This is too low. You need to do more." So that'll be part of this process. I don't know if that answers it, but...

Sean Lane: No, for sure. And then basically as long as you stay within that paired metric, I like how that's almost a check and balance on your growth. Then you get to make those decisions that you're talking about with your sales leader about head count and ramp and things like that within your business unit. And then again, that's on you to make that planning happen.

Ryan Toben: Yes. That is the goal. That is the goal. It's easier, it's very simple when I explain it right now, but crosstalk if there's another global pandemic, who knows?

Sean Lane: I'll check back in in a few months. Before we go, at the end of each show, we're going to ask each guest the same lightning round of questions. Ready? Here we go. Best book you've read in the last six months?

Ryan Toben: Okay. Humankind, a Hopeful History, a guy by the name of Rutger Bregman. It's basically a different perspective on human nature. It's awesome.

Sean Lane: Cool. You're not necessarily in ops anymore, but I think the question still works. Favorite part about working in ops?

Ryan Toben: I like finding trends that are actionable, seeing something in the data that tells us something that people didn't see before, and then bringing it to light and to helping change the business because of it.

Sean Lane: Other way around, least favorite part about working in ops?

Ryan Toben: Having to deal with when the tech breaks, sometimes some sort of flow doesn't work.

Sean Lane: Things you don't miss.

Ryan Toben: Yeah, exactly.

Sean Lane: Somebody who impacted you getting the job you have today.

Ryan Toben: So a guy by the name of Alex Saleh, he is now the COO at ON24. He was the VP of ops at SuccessFactors when I first got the role there. He hired me, we've stayed close over the years. He's somebody that I always lean on, think about like,"What would Alex do?" I ask, he's always there to answer questions when I'm debating topics. So he would be my person.

Sean Lane: That's awesome. And last one for you, one piece of advice for people who want to have your job someday?

Ryan Toben: I think that if you're in ops and you want to get out of ops, you are going to have to put yourself in some uncomfortable positions and potentially ask for it, push for it, but also be willing to take a side step. I had gotten to the point where as a VP of ops at the time for a while, reporting to CEO, in every big meeting that happens at the company, from assessing an acquisition, to deciding a department that we're going to add or get rid of and all of the board meetings and big stuff, and to take the role, it was not in pay. Frankly, it was still an increase in pay because salespeople make more than ops people, which shouldn't be a shock to anybody, but in responsibility or in level of visibility, I definitely took a step back in order to go into sales, but I think it's still going to be the benefit for me in the longterm. And I'm still probably not even back to where I was, but I personally think it's worth it.

Sean Lane: Thank you so much to Ryan Toben from Gainsight for joining us on this week's episode of Operations. If you liked what you heard, please make sure that you are subscribed to our show so that it shows up in your feed every other Friday. Also, if you feel like you're learning something from this show, please leave us a six star review on Apple Podcasts, six star reviews only. If you are new to the show, what that means is leaving us a five star review on Apple Podcasts and leaving us six stars in the comments, because that's just the way we do things. All right, that's going to do it for me. Thanks so much for listening. We'll see you next time.