Our host Jeff Ignacio sits down with Jeremy Donovan, Executive Vice President of RevOps and Strategy at Insight Partners. They discuss how to optimise your hiring process, create cadences, and perfect your org structure. They also look into what it means to be in the business vs on the business and performing due diligence.
The RevOps Review
The RevOps Review - With Jeff Ignacio and Jeremy Donovan - Operating As A RevOps Advisor
(upbeat music) - This podcast is brought to you by Cognism. Cognism helps businesses connect with their dream prospects by providing premium contact, company, and event information, including firmographics, technographics, intent data, verified business emails, and verified mobile numbers. - Hey Jeremy, how's it going? - Not great to chat with you, Jeff. It's been a minute, so excited to catch up. - Yeah, I think the last time we connected was probably 2021, or yeah, maybe. Yeah, I think 2021 was the last time you and I had actually connected live, so I'm really grateful for the opportunity to have you on the show. So I'm gonna introduce you, correct me if I'm wrong in any particular way, but you're currently the EVP of revenue operations and strategy at Insight Partners. I myself had operated at an Insight Partners Portco, tremendous help internally, tremendous amount of resources, but I'd love to pass it off to you to introduce your role and what you're currently up to. - Yeah, so, there's a long history of many different roles, but most recently, before I was doing this, I was doing different operating roles as a revenue strategy and ops person. So I moved over to Insight about two and a half years ago, and technically, I guess that styling is not 100% accurate. My day-to-day is advising our 500 plus portfolio companies on their revenue operations and strategy. So I get to do a lot of high-level advisory. If there's one thing one could miss in this role, it's that last mile, right, is you have an idea and the idea can often be, you know, maybe there's something you have done before, so it's not academic, but sometimes it's academic, and you get these ideas, and then when you go to put them into practice, you gotta do a lot of change management on the people side, you gotta do some process tuning, you gotta do some tech tuning, so I don't necessarily get that in this role, but I do get to see a ton of different, we're all B2B SAS, so I get to see it, but even so, like a ton of variety of different operating models and go-to-market models. - So you shared with me that there are kind of three key, kind of areas of interest at the moment, and I wanted to just kind of leave them out with you, make sure that these are definitely the topics we want to cover today, so the first is kind of the vetting out process at some at the personnel level and leadership level, so the Chief Revenue Officer in particular, some of the interviewing you're doing. Second is that go-to-market due diligence, I'd be very curious to hear from you, you know, now that you're still an operator, but you're not necessarily internal to these companies, like what should they be prepping for when they're engaging with a company like yourself or with other investors? And then lastly, some of the ongoing advisory that, you know, I have experienced firsthand with one of your other peers, so, you know, what does that look like? But first, I'd love to dive into, you know, vetting out the kind of the leadership team, you know, why do companies, you know, need to kind of have additional support from companies like Insight Partners? - Yeah, I think it's, I was actually talking to another person in our space that I respected, Tom and Andy Millott, I don't know if you ever had him on the podcast, he's had a Brevopsober at CARNA. And we were, we were geeking out on this a little bit. And, you know, so often when people are hiring for, you know, especially a sea level position or scaling up from rather small, like there's nobody in the company who actually has done that job. And so like it take the case of a CRO, I mean, the CEO may have more often than not, you know, comes from product background in a lot of SaaS companies. So they have never really been a CRO. So they themselves don't necessarily know, you know, how to interview that person. So that's where we come in. I mean, they're definitely doing interviews across their companies, CEO, right, CMO, CXOs, whatever are interviewing this person. But they'll call on, you know, their investors to see if they have somebody who has been there done that. So I was a CRO at one point and that before moving into RevOps, which was more my groove. And so, you know, having done this before and certainly having interviewed now, right, hundreds and hundreds in the last two and a half years of potential CROs, like I'm getting, I'm getting or finding my skill of doing that. And I do try to track my false positives and false negatives. So a false positive is, you know, we say yes, they say yes to hire the person. They don't work out what happened, right? A false negative is, I say no. They still like the person and hire them. It does happen. And then that person turns out to be great, like why was I wrong? What, you know, why was, why did I say no and what could I have detected differently? So I do try to, you know, I do try to track those things and calibrate, but that hopefully makes me, you know, more or more helpful. I would summarize at the high level and then I'll pause, but the biggest thing in hiring a CRO or like any, into any position almost is basically been there, done that. And I could expand on been there, done that. But that's, that's, I would say the number, like the overarching theme of the stuff that I look for. - Do you ever find that folks who've, you know, just use like an analogy, they've climbed from base camp all the way up to the type of top of Everest, you know, the next challenge is, okay, let's do, let's run it back and do it all over again. Do you find that folks sometimes tire of that journey or are there plenty of folks out there who say, I'm ready to reload after a little bit of a break after that last journey? - It's a, it's a mix. And you definitely, right, you're always listening for subtext and what their, what their energy level is. And it was also like, what's base camp and what's Everest? So, right, if base camp was one million and Everest was 10 and they want to go back and do a million again, like, yeah, I think that that's, I've seen plenty of that and I've seen plenty of successes or, you know, maybe it's 10 to 100, right? Where I think it's, it's very different is if base camp was 10 million and then, you know, eventually they find themselves in a multi-billion dollar company where, you know, my joke is like everyone's assistant has an assistant. If they're in that world and they, and they like, when I definitely see these people is that they, you know, they went to this big company. They never had a big exit. They hear about all, you know, they think, well, right, is we have this confirmation bias or selection bias that we see these people who had great exits and we think, okay, I want to do that too. And then they want to go back, you know, and, and join a series B or series C startup so they can have, you know, the big exit. Those 10 more often than not to not work out because they're just not ready, they don't remember. Like you just, they don't remember what it was like to have the ground shifting on you every day. And they don't remember what it was like to have to jump in on deals, right? And really, really roll their sleeves up. They, again, this is sweeping generalization 'cause there are some who are successful at it but I would say like I'm playing in my mind or sometimes actually with data like Moneyball. And if I'm, if I want a statistically higher chance of success, you know, the multi-billion dollar or whatever Oracle Salesforce, AWS, whatever person, coming back into a series B or series C startup, like that first bounce back into one of those companies is a very low success rate. Like you really want them to, you know, have pretty recent scale up experience as opposed to working for a BMF. - That's super interesting. So then let's transition a little bit to the go-to-market due diligence side of the house. So as an internal operator, I'm generally accustomed to operating cadences, building into business and then on to business at different various times. At this time of the year, it's August through February. It's the annual planning, the t-shirt sizing of product investments, account segmentation, et cetera. But from the outside looking in, you don't get to see all of that. So how do you, you know, what are you looking for when you're performing a due diligence at the organizational level? - Yeah, there's like a set of areas we drill into. So I'll outline them and then give you one or two examples in each. So the first thing is literally like a go-to-market category. I'll talk about that in a second. The next one is process, both pre-sale and post-sale process. The next one is team and talent and org structure. And then the fourth one is the most important actually. It just, that's just the order we kind of go things in. The fourth one is pipeline and performance. There is a fifth that we never really talk about in diligence, interestingly, which is their tech stack. I thought we would get much more into tech stack in diligence, but it tends to not be a differentiator amongst companies. So just like one or two examples need to those categories. So in go-to-market, that's things like ICP and segmentation. Whether, you know, whether your PLG, SLG, sales-assisted PLG, you know, partner, land, whatever it happens to be. So that's the go-to-market side. The pre-sale and post-sale process kind of obvious, like what does your pre-sale process look like? What is your operating rhythm and cadence of pipe gen activity, of deal inspection activity? You know, are using medic or whatever? And to what level of discipline are you using for deal inspection on the post-sale side, right? We might drill into their implementation processes, professional services, customer success, like and renewal and upsell processes. So that's much more, as I said, process focused. And the third category of like team and talent and org structure, the main thing we're probably going to look at there is repotainment, what percentage of reps are meeting or exceeding quota over the course of the last whatever 12 months. But also, you know, thinking about those things we talked about with respect to this zero hiring, we're betting the seros on that level too. And then as I said, the most important thing is really pipeline and performance. So there we're really getting into, you know, we want them to give us obviously under NDA, a list of their pipeline, their, you know, current open pipeline. And then we will do a deal, you know, we'll do a series of deal reviews. You know, if they're enterprise, it's going to look more more medic-like, right? And we're going to go deep on those deals. And what we're listening for is like, yes, we're vetting the deal itself, but we're also vetting the leadership because if they're selling into enterprise and they don't know the deals, that's a big red flag, right? So they really have to be able to talk to the deals even though they're not the individual reps. If it's a super transactional business, then we don't expect, you know, them to, it's going to be much more about that pre-sale process side and much less about the pipeline 'cause they're probably not going to know, you know, Joe's pizza shop, right, the same way they would know selling to a large enterprise. - Now that makes perfect sense. I think a couple of things here, you know, I think a lot of folks, you know, at least when I'm talking to revenue operators, you know, we can over-index on pipeline performance and process side of the house. But I think go to market category and team talent or structure are actually just as important. And I'm curious as to, you know, when you're working with these teams or, you know, in these four or five areas, you know, where do most of these companies that you're operating with? Where do they shine and where are some of the areas that they can improve on? - It definitely will vary. I mean, I would say that it depends right if this is a $10 million ARR company or is this a $100 million plus ARR company? I would say everybody could be more rigorous on their operating rhythm. Everybody could be, right, is really consistent pipe gen. Really, really consistent deal inspection. Like to me, I think that's maybe the number one area. Or structure, you know, you can debate about whether in various contexts having whatever separate AEs and AMs or combo people like make sense. I mean, I do have a point of view on that, which I've actually built decision trees around and even code so that you can kind of enter what the context of your organization is and then have it output the recommended structure. But I don't think that says needle moving as like pipe gen and deal inspection. And yeah, on the go-to-market side, the big change there obviously is around efficiency that before, right, everybody, I'm not saying anything as I've been said 100,000 times, right, we went from growth at all costs to efficient growth. And there, I do think being really thoughtful about the distribution of like how you distribute your bookings target across different channels, that has become more and more critical. Because yeah, if you're whatever outbounding and you have a $20,000 ASP product, you're probably never gonna be profitable. - So recently I was advising a company that had pretty low MRR at the user level. So you're looking at 50 bucks a seat and a number of seats per customer was about five. But yet they had a high touch customer success motion. And without even running the numbers, my suggestion was, okay, you guys gotta figure out a low touch motion here. Just 'cause you're probably not gonna pencil, just the cost of retention. And if you have the scaled in early, you're gonna break the bank. So I'm curious when you're, 'cause I think these due diligence happens in a couple of places. One is a big fundraising event, which doesn't happen very frequently, but then you do have these quarterly forward meetings. And then even better, you have the internal management meetings. What's a suggested set of cadences that you would put out there for senior revenue operating leaders to one, maintain a healthy view of the business on an ongoing basis so that you can lead up to that board meeting. - Yeah, I mean, I think, well, I'll talk about two different kinds of cadences, I guess. And you used the language earlier, which is in the business and on the business. I think the in the business stuff, yeah, is on that quarterly cadence. And there it really is about what days are your one-on-ones? What do you do in your one-on-ones? What days are your team meetings? What do you do in your team meetings? What's your approach to enablement, right? All the usual suspects on the week-to-week thing. And then we do have a recommended, and it's a public asset that people can find on our blog, but we do have a recommended cadence for like your quarter as well, of in which week do you review your current quarter-ops, in which weeks do you review your next quarter-ops, in which weeks do you turn on like a war room equivalent towards the end of the quarter, in which weeks are you doing QBRs? So we do have a recommended cadence around that for revenue leaders to follow. And our approach is like, is much more poll-oriented than push-oriented. So we have these resources available to our portfolio companies. They don't have to follow them, right? They're meant to be guidance. So a lot of folks will take an asset like that. In fact, I did in my prior company, Insight was an investor in sales loft, and that was my favorite asset was that cadence asset around how you should structure your weeks and days of the week and weeks of the quarter. And then the on-the-business piece, which was the other side, that 10, I mean, it depends on how fast you're growing and how fast things are changing, but I mean, that does tend to be much more of an annual thing from what I've seen. And we're getting now into that season for a lot of our portfolio companies. So that definitely does change the nature of the questions that come in, 'cause this is the time of year where they start to think again about compensation structure, around territory strategy, around role definition and org design. So this is definitely the time of year where that kind of stuff comes up, where that's a much more on-the-business approach. - So then lastly, we wanted to go over three topics. Second, third one is I think unique to the role and the business that you're in. Ongoing advisory and content production. So I know I attended GTM 2023 last year with Pavilion and Insight was kind of a huge co-partner to that event with a bunch of workshops. And then I think you also had an on-site with your port codes. Can you tell me a little bit about the ongoing advisory and what do you mean by content? 'Cause I'm generally thinking about marketing content, but I think you're talking about something different entirely. - Yeah, yeah. So we're doing the same thing again this year. I think it's in Austin where we're hosting our port codes for a day before the Pavilion conference and then going into the Go to Market conference. So yeah, ongoing advisory. Most of it is like someone has a question about maybe a strategy change that they're doing. So I got one this morning that was an interesting approach to how they might redesign their sales compensation for next year based on the fact that they do very small lands but then they call it an explosive expansion. So they might sign whatever 50K land and then go to two, two and a half million within two to three years on a rather predictable timeline. So, but in that instance, like how do you comp your reps? Especially when the land is really hard. So it's like a really, really hard land for a really small amount of money. How do you comp reps on that when you know that that's going to turn into something much larger down the road? So like those are the kinds of questions and it just runs the gamut. And then the, yeah, the other side of you asked about content production, yeah, it's interesting because we're not, you know, like why do we produce content? The majority of the reason we produce content is to help our portfolio companies, but we put 90% of it also out there in the public domain and that could be like benchmarks are super popular. So we publish a lot of benchmarks on like operational benchmarks. We've also been working on some staffing benchmarks that we'll be releasing at some point soon. So like what should your organization look like when you pass 200 employees, when you pass 500 employees and not just go to market but every function within the company. But then yeah, some of the other assets I think it was like play also as playbooks and guides, right? So I think it's the same kind of content. Say on the, you know, we have a sales and marketing center of excellence, sales center of excellence and marketing center of excellence of product and pricing center of excellence. And we're all producing content that is intended to be, you know, thought leading content, part of which is, you know, I think the philosophy of, hey, you know, we have 5050 experts on this onsite advisory team who are thought leaders and can help guide you if and when you become an inside portfolio company. So there is marketing value to it. It's just not the same as working for, you know, regular SaaS company. - I think what's interesting is, you know, let's say I work for Portco and, you know, if you're early stage, you're generally a team of one revenue operating team, but to have someone in your corner that you can, you know, ask questions to you be a sounding board, I think is a wonderful asset that, you know, to exercise, but even for the larger firms, sometimes you get this tunnel vision, right? You have this internal business context and it's really difficult to have an out of body experience. So like really assess the business on a neutral basis. So I found that extremely valuable to have like a set of advisors or partners that I can work with to really, you know, challenge me to see the business from the different angles. - Yeah, on that note, I left something big out on the advisory side, which is our, like my goal/our goal is not for any one of us to have the answer, right? So our goal is to get the Portco the best right answer that we can. So sometimes that is I know the answer. Sometimes that is I have a colleague in, you know, out of the 50 of us who knows the answer, sometimes that's not the case. And, you know, the answer is to link them up with someone else inside or outside of the portfolio who does. Like I had a Portco who was scaling very rapidly and wanted to know more about how do I, like, build a recruiting, a sales recruiting engine that is high velocity and high quality. And I might have some thoughts about that, but I've not been in recruiting, right? So that was an instance of where I phoned the smartest person I know on building a sales recruiting engine and linked the Portco up with them. And then I love to be a fly on the wall for those calls. So I don't just facilitate them connecting. I lurk in the background on those calls and I'm taking notes furiously and, you know, and then I try to turn that around. And I do put a lot of content now out, not just through insight, but obviously I'm linked in. And then I created, when I started with inside, I created a, if I had known about Notion, I wouldn't use Notion, I guess, at the time. I didn't know about Notion. So I'm just using a documentation, like blog software called revenue-playbook.com. And it's all free, but like every time I get a question, I document the question and the answer to that question on that playbook. And, you know, two and a half years later, there's a lot of stuff in there. So I would say almost eight or nine times out of 10 now when I get a question at something I've answered before and can just redirect the person. Like I had another one today, which was, I've got some great reps, but we're selling into a soft demand environment. How can I keep them financially motivated? And was not the first time I'd gotten that question. So I was like, ah, okay, I got the answer to that. And I've got a whole section on that as a resource for them or anybody else to go through and see what the recommendations are in that context. - Amazing. So last question for you, for the revenue operators that are listening, what one piece of advice would you wanna leave to the audience? - Yeah, well, my bias is basically like, I'm hyper analytical. So I think we're also just in an era where data driven decision making, there's more and more data, it's more complex to deal with, but data driven decision making is increasingly valuable. And AI, like gen AI is not gonna solve necessarily all of your problems. And machine learning is, stuff is probably even more relevant on the rev-op side. So my advice is just, is just like sharpen the saw every day on the analytical and technical side. Even if you're a leader, you have to know the art of the possible with respect to like what you can do in whatever in VBA and Google Apps Script and SQL and Python and whatever, you know, apex for sales force. I think you just need to know the art of the possible. So I would just encourage people to double down on their, like really next level, 201, 301 level analytical skills. - Now for the folks who want to connect with you and learn more about you and what you're doing, how can working folks go? - Yeah, pretty, as most of your guests probably answer, I'm hyperactive on LinkedIn. So I do respond to, you know, all pretty much all legitimate direct messages. You know, if you try to sell me a franchise or, you know, longevity supplements, I'm gonna ignore you and block you. But if you have a little legit sales or revenue related question, I'm always happy to engage. - All right, Jeremy, appreciate you. You're always a real one. - Thank you, thanks, Jeff.