20Sales: 12-Week Step-by-Step Framework to Crush Every Sales Quarter | Moving from SMB to Enterprise: How and When | Verticalised Sales Teams: Why They are a Gamechanger and How to Build Them with Ben Fiechtner, CRO @ Clari

Ben Fiechtner is Chief Revenue Officer at Clari, where he drives global go-to market & revenue operations. Ben previously served as SVP at UiPath, growing their key accounts and regulated industry verticals from $150m to $450m. Before UiPath, Ben was at Salesforce where he held multiple senior roles, achieving significant year-over-year growth and always on the bleeding edge of Vertical teams. In Today's Episode with Ben Fiechtner We Discuss: 1. How to Close Deals Faster: What are the top 3 ways sales reps can increase urgency in a deal cycle? Should reps be discounting? If so, what level can be appropriate? What is the right way to ask prospects for their internal buy process? How do you know if you are dealing with a champion? What are the single biggest reasons that deals are delayed in closing? 2. SMB to Enterprise: How and When: When is the right time to move into the enterprise? What are the single biggest mistakes startups make when making the transition? How does Ben advise startups to do it but with minimal spend and investment? 3. Verticalisation: Why, When and How: Why is it important for founders to consider a verticalised sales strategy? What are the benefits? When is the right time to consider a verticalised approach? What is the right way to resource each sales team for a verticalised approach? What are the biggest mistakes companies make when verticalising sales teams? 4. How to Hire the Best Reps: What are the top signals that a candidate will make for an amazing sales rep? What question does Ben ask in every interview? What do the best answers have? What are the biggest mistakes founders make when hiring sales reps? How fast do you know when a hire is a good hire or not?

Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.

• 0:00Speaker 00

  You're looking at four different aspects of the business. Create, convert, close and churn. Those are the four buckets. I tell people all the time, salespeople aren't lazy. They just are wired to find the quickest path from point A to point B.

• 0:11Harry Stebbings?

  This is 20 Sales with me, Harry Stebbings. Now, 20 Sales is the monthly show where we sit down with the best sales leaders in the world to discuss tips, tactics and strategies for startups to implement today. And today, we're joined by Ben Fikner, Chief Revenue Officer at Clari, where he drives global go-to-market and revenue operations. Ben previously served as SVP at UiPath, growing their key accounts and regulated industry verticals from, check this out, $150 million to $450 million. Before UiPath, Ben was at Salesforce, where he held multiple senior roles, achieving significant year-over-year growth. But before we dive in, we need to talk about our sponsor for the day, Clari. Clari is an industry-leading AI-powered revenue platform

• 0:54Harry Stebbings?

  that is purpose-built to help companies optimize their end-to-end revenue process. With over $4 trillion in revenue under management, Clari's customers have a material advantage to optimize their enterprise revenue process across all teams, from rep to the boardroom, by leveraging the world's largest and fastest-growing AI reservoir of enterprise revenue expertise. More than 1,500 organizations, including Okta, Adobe, Workday, Zoom and Finextra, run revenue on Clari to improve win rates, prevent slip deals, forecast with accuracy and boost the productivity of all revenue-critical employees. To learn more about how you can create, convert and close revenue with Clari, visit Clari.com.

• 1:35Speaker 00

  You have now arrived at your destination.

• 1:38Harry Stebbings?

  Ben, I am so excited for this, dude. I have heard so many wonderful, but also interesting things from many mutual friends. So, thank you for agreeing to do this.

• 1:47Speaker 00

  I cannot wait to get started. I'm excited to spend the time, Harry, and a little bit nervous about those interesting stories you've probably heard.

• 1:53Harry Stebbings?

  As I said to you before, this isn't your first time on the big screen because your first time on the big screen was when you were a young entrepreneur, starting a t-shirt company. Just talk to me about the t-shirt company in college banners, the starting point.

• 2:05Speaker 00

  Love that we're starting here. So my freshman year, a buddy of mine, Troy Vosler, and I lived in the same dorm and we were both nerds in high school where we did a lot of t-shirts for sporting events, student council, all of those things. There was a time when like every rapper was getting into apparel. And so we were thinking like two kids had maybe one or two different or adult beverages on a Wednesday evening. We're like, we should start a t-shirt company. There was this word sconny, which is kind of the equivalent of cheese head in the state of Wisconsin, which is, you know, being proud of all things Wisconsin, brats, cheese curds, drinking PBR on your John Deere tractor. We trademarked the word. We sold, we both invested three hundred bucks out of our own money and like sold out of t-shirts in probably two days. And at that point, we were like, holy cow, we're on to something. We set up an e-commerce website.

• 2:48Speaker 00

  We started a wholesale business and it was just right place, right time. And it's still like Troy's still running the business and it's going really, really strong.

• 2:55Harry Stebbings?

  Whoa, whoa, whoa, whoa, I didn't realize that this actually worked. No offense. I thought it was like one of those that like crashed and burned. Wait, so it's still running today and Troy still runs it today?

• 3:05Speaker 00

  Yeah, yeah. So there and there's a bar now across the street from the stadium. There's a microbrew like beer that's sold throughout the Midwest. Yes. And a lot of what happened was it was actually one of the most unbelievable experiences, I think, for both Troy and I. And I don't want to speak for him, but you know, I thought I was going to go to politics. I was going to be a lawyer, all these things. We sold our first big t-shirt deal to the University of Wisconsin bookstore. And at that point I was like, holy cow, I love the sales thing. This is much more for me and more of my speed. So that's how I actually got into sales, I would say. And that's how I picked this as a profession, one. And two, I mean, over our four years, it was insanely successful, I would guess, I'd say in terms of notoriety and brand. We ended up actually having our wholesaler, who was a buddy of ours as well, that actually held everything, held all the

• 3:47Speaker 00

  inventory, shipped it out for us. So we just kind of took a margin and ended up really, really minimal work for a lot of brand building and guerrilla marketing that was super fun to do.

• 3:56Harry Stebbings?

  I'm a little bit embarrassed now. I didn't realize it was quite that successful. You shouldn't be. This is great. Did you keep the equity?

• 4:02Speaker 00

  He bought my shares out and I forget what year that was. Remain friends to this day, but he's actually got everything to it. And I'm more a kind of the emeritus sconny person, if you will, who probably claims more credit than I should these days.

• 4:14Harry Stebbings?

  That's amazing. And so as part of that, you mentioned the love of sales, like coming from selling that first large agreement. What did you love about sales? Like what was it specifically?

• 4:23Speaker 00

  Funny thing, going back to the point of like, I thought I was gonna be in politics. I thought I was gonna be a lawyer. I was pre-law, all these things. I don't know. I was dumb enough and young enough that I looked in the Yellow Pages, saw the biggest ad print name, called the lawyer, took him out to dinner. He and I went to the most expensive steak restaurant in town because I knew he would actually pay even though I'd offered. And he said, look, Ben, how many t-shirts have you sold tonight? And I was like, uh, five. He's like, how much you made? I'm like, seventy-two dollars. Like, I gotta go back to an office to make more money and work more hours. You found a hack, right? So that was one that was like, kind of steered me away from it. And two, what I realized about what I want to do for that profession, not that I loved arguing, but I love sharing points of view and love trying to help people see things that maybe they hadn't seen clearly,

• 5:00Speaker 00

  which was debate and politics and law for me, which then when we won our first deal with the university bookstore, it was kind of helping them to see a completely different market that they hadn't had because they hadn't changed designs, they hadn't changed approach. They hadn't actually marketed or shared a message that students really cared about in a long time. Kind of that ability to convince somebody to see my point of view, one, and then two, like, win, was super, super fun for me and like the thrill of the adrenaline, the hunt that like I got addicted to and knew I was gonna be a salesperson.

• 5:29Harry Stebbings?

  It's so funny though that you said about that because I am fascinated. I heard so many great strengths that you have. And one of them was kind of teasing out from customers what they want. And also, as you said, getting them to see your point of view and convincing them. What are the biggest lessons in getting customers to see your points of view? What questions do you ask? What works? What doesn't? How do you approach that?

• 5:50Speaker 00

  Two things on this. One, the majority of organizations I've been a part of, like, have been on the maturity cycle where a lot of tech companies become as product sellers. They talk about me, me, me, me. Here's all the great features and functions. Here's the bits and bytes. I think the first thing in terms of like, not that you're convincing someone to see their point of view, you're showing up with an opinion, right? It's the same thing as if I go to my boss, I can't say, hey, I have a problem, right? It's more, I have a problem and here's an idea I have to fix it, right? And the same way when you're talking to a client, I think what we teach a lot of our sellers is really study their business. It's the easiest thing that you can do. And if you show up with a strong opinion of, hey, I've talked to your team, both qualitative, quantitative research that says, here's my perspective on where you should be going. And here's how I uniquely help you get there.

• 6:33Speaker 00

  You may not always win, but you have a disproportionate chance that you're going to actually have a seat at the table to help that person solve their business. And candidly, like, I don't want to buy, and I buy enough software from people that don't know my business inside and out, and don't have a unique way to solve the problems I have. Like, we're not in an era anymore of just buying tech for tech's sake. So that's what I think about that. When you're talking about, how do you bring people to the table? Yes, you ask a ton of questions, you do all the right things, but most importantly, before you got to know someone, you do your homework, right? And show up with an executive point of view, if you will.

• 7:03Harry Stebbings?

  One of the things that someone said was a superpower of yours was creativity when it comes to deal construction. And I want to get it right. They said, when it comes to deal construction, you're one of the best in the world. Taking the go-to-market team on the journey with him as we work to cultivate this muscle. What makes you so good at deal construction? And what is good deal construction?

• 7:23Speaker 00

  I don't know who taught me this, and I think a lot of great mentors, probably at Salesforce, that leaned into this. One of my first great bosses for a long, long time, Eric Eichensiders, where he was like, you own pricing. Like, no, I don't. Like, I have to go through all the approvals. I have to ask for this person, and this person will approve. You ultimately get to approve it. He's like, no, you own pricing. So what was ingrained in me early on was my job as a seller is to understand the client's constraints as it relates to their OpEx, CapEx, cash flow, whatever it may be, and the constraints that they have, which often is tough to figure out. Because sometimes it's, yes, the buyer knows it, but sometimes the procurement knows it. More often than not, it's a finance person that you never talk to. But if you can figure out through options and through the right questions, what constraints they have, and then you really understand the levers you have internally. The superpower has been with a lot of training from a lot of great mentors over the time.

• 8:08Speaker 00

  Like, how do you thread that needle of your constraints, their constraints, and find a win-win situation? But a lot of times, I think folks just say, here's my pricing, here's my discount percentage, do you want to buy? Versus truly understanding budgets as it relates to operating expenses, cash flow, CapEx.

• 8:23Harry Stebbings?

  What questions do you ask to understand that? Imagine I'm an angel investment of yours, and I'm a great product founder.

• 8:29Speaker 00

  Yeah.

• 8:30Harry Stebbings?

  Dude, I don't get this, and I'm trying to run sales myself before hiring my first sales rep.

• 8:35Speaker 00

  Yeah.

• 8:35Harry Stebbings?

  What questions do I ask to find that out?

• 8:37Speaker 00

  I think that the way that I've always done it is, and it depends on if it's a named user model or a consumption model, of course, but like, looking How do you want to buy? I'm not going to force you on how many users, how many of those things like let's just understand your deployment schedule, what you want to do and work backwards from there. So, once you've mapped out the deployment schedule of call it the business as usual for when users need to be live based on the value that you're going to expect or kind of the business impact against the complexity to implement. Lay that model out and you're working together discovering that as they go. The second piece of that then is look, as we look at this, here's my levers is how I've always negotiated. It's usually service start date, commercial terms, length of contract. Those things are the biggest levers for traditional SaaS companies. I'm going to tell you about those immediately. Where do you have flexibility?

• 9:22Speaker 00

  And then we kind of marry the two. But a lot of it is understanding what they're trying to achieve and then understanding what levers you have internally and just marrying them together.

• 9:29Harry Stebbings?

  What levers are you most willing to move on and compromise on?

• 9:33Speaker 00

  Without giving too many secrets about how to negotiate with Clary on the most popular sales podcast. I think the thing that we care the most about, of course, is number of users. So, the bigger the population, the better the price you're going to get. And that is true for every named user company. Same thing on consumption, the more you're going to commit to, the better rate you're going to get. Next for us is service start date. So, how quickly can you get them? SaaS companies can't recognize that until they actually activate users. Meaning if you're going to activate six months from now, I'm not taking it until Q4. Q2 deals are worth a lot more money to me in that sense. And the third thing is like length of the contract. Fourth thing is always probably terms and conditions of simple things, payment terms, whatever it may be. And creativity around T's and C's.

• 10:12Harry Stebbings?

  Okay, what about pricing? How do you think about discounting? It's why it's so interesting, some weaponize it and some are like no.

• 10:18Speaker 00

  A lot depends on the maturity of your sales team. You have to have guidelines in place just for safeguards and governance to not do anything silly. But I truly do, and I've told my sellers at the last three companies I've been to is like you own pricing. If you come to me and help explain why this is important for the client's success and why it's going to make them successful within staying with reasonable guide rails, we're going to give you the pricing you need. I think that's ever true now where we look at macro economic environment, SaaS going in the tank. Like we got to be focused on adoption and long-term success. And there are times when people talk about creative deal construction like. Yeah, we've done crazy ramps to get people off the ground because they were tight, but we knew it was going to be a long-term contract that was going to help them.

• 10:59Speaker 00

  We've done unnatural things. If we know enough and the client is willing to share what their constraints are, we can always find a way to solve it.

• 11:06Harry Stebbings?

  Is there anything that I can do to instill urgency in a deal? It's another thing that I find really challenging. I sit on the board with a lot of companies and they're like, we can't get urgency in the sales cycle. Any tips there?

• 11:16Speaker 00

  I think beyond the traditional, let's drive a compelling event, right of working backwards and figuring out something that's going to solve for them uniquely. That's a burning platform issue. That's obviously the most consistent and easy one. I think the other thing is finding the personal win, right? So for your champion, your buyer, the economic buyer, hopefully you're figuring out what the win is for them and helping them. Be it relationship building, be it storytelling, be whatever it is, like getting in the boat with them. I find a lot of times like in not asking for personal favors or those types of things, but if someone feels connected to you and connected to the product and feels connected to the success of the project, they're going to push to get it done urgently as well, which has been the probably the thing that I would use most successfully out of the traditional things we've done.

• 11:57Harry Stebbings?

  Do you go for multiple champions in a sales process? And if so, how? I always think it's a hard one because it's like, Ben, can you introduce me to your wider team? Because you might not be here, you might get hit by a bus or leave, in which case I want to close this deal.

• 12:11Speaker 00

  Yeah. And I think when I was a seller, I think I did this with trying to fourth wall folks from the human element of, you know, I'm a salesperson, you know, it's my job and you know that like, which is great about my current job, like I sell the sellers. So it's super easy for me to say to the CRO, like you've been in my shoes. You know, I got to talk to the CFO as well and I got to make sure that I understand his or her constraints to figure this out. I think I did the same thing as a salesperson. A lot of times was just trying to make it a human element. If you come off in full salesperson cheese and say, Harry, I really make up some bullshit reason as to why you need to get to so and so. They're going to smell right through it. And honestly, authenticity is the one thing that matters there. So I think what I always did was like candidly, I'm a salesperson and you know, it's my job to triangulate on this.

• 12:54Speaker 00

  So I don't waste my team's time and I don't waste your team's time. Can I have an introduction to X, Y or Z? Nine times out of 10, it worked.

• 13:00Harry Stebbings?

  Is there anything that we should or shouldn't do in terms of payment terms and conditions? Is there anything that you're like, no, actually I've learned, be careful on that one.

• 13:08Speaker 00

  Look, I think the deferring payment terms for a terrible long time because someone is in a tight cash position usually ends poorly. You've got to make those bets really, really intelligently. And I've done that and I know people have been strapped and you felt for the customer and you've wanted to put them in place to continue them as a client. But those ones are really, really careful and I would tread lightly on that. I think you're seeing cash becoming exceptionally more important, especially with interest rates as high as they are. So people are tightening those windows and it's somewhat becoming standard across the board. So there's less give and take there.

• 13:38Harry Stebbings?

  Are you seeing buying new tech much less? Like people talk about CFOs tightening budgets, centralizing. Are you seeing that?

• 13:45Speaker 00

  It's funny. So most of the CFOs I talked to are like, we're spending the same, we're just spending it on different things. And I think that one, that means there's enterprise tech consolidation. So they're trying to say, hey, I can do as much with one platform as much as humanly possible. I don't need 12 best of breed products. Two, I think you're seeing folks dabble, obviously with Gen AI. And we got to mention it 10 times on every podcast we're on, right? But you're seeing people shift money there and spend more money there. And that does get exceptionally expensive in certain spots. But I don't think folks are buying less. I think they're just buying differently. And from what I've seen, it's been more platform based approach. And it's been more platforms that have proven success rather than just the shiny object.

• 14:25Speaker 00

  So if you can show material improvement on an ROI of bottom line, you know, constriction, top line growth, whatever it may be. Folks are interested, but if you're just there because you're a shiny object, yeah, you're getting cut.

• 14:36Harry Stebbings?

  What about forecasting? This is your business. How the fuck do you forecast accurately in a world where traditionally like the joy of SaaS was like, you know, you had your kind of everyone stayed and you added 20% and it was a great business. But now the accuracy of forecasting is so hard. For me as a founder, how do you advise me on how to forecast accurately in a time of volatility?

• 14:58Speaker 00

  I think three things. One, how do you drive the most simplistic process? I tell people all the time, salespeople aren't lazy. They just are wired to find the quickest path from point A to point B. So you have to make it super simple, super straightforward. I think the second and third thing that I've learned a lot about being in my seat now is the process really matters. So there's a lot of forecast calls and I get to meet with a lot of. CROs and I'm fortunate enough in that situation, like forecast calls you listen to and they're like, hey, this deal's still good. And we're like, yep, that's their forecast call. Versus, I think where we looked at this at UiPath and then again at Clary was how do I drive a 13 week revenue cadence for the quarter that I'm going to actually chunk up into different four segments?

• 15:35Speaker 00

  So one example of this would be like, week one, we're all looking at the same data that says, hey, here's my slip deal reviews. Here's my deal back walk up. Here's my commits. And the reason you're doing that, so everybody's looking at the same page is just so that frontline managers are all asking the same questions. AEs all know what to expect. And that as a senior leader, you have the opportunity to manage by exception to say, where do I have a hole in the business? Is it top of funnel? Is it conversion? Is it execution? Or is it churn and retention? And that's where you're figuring out how to dial in. So long-winded way to say, one, tooling matters. Yes, of course. B, process matters as much if not more on how you're actually engaging over the 13 weeks quarter.

• 16:14Harry Stebbings?

  I just have to dive in on the 13 week cadence and how to run that. Just break that down for me. What are we doing week one?

• 16:21Speaker 00

  So week one, right, the first week of the quarter, typically I'm looking up how the slip deal reviews. So one, you're looking at slip deals, everything that happens. A, because that's the easiest way to the path to commit. Those are deals that were supposed to happen. That's not me beating up people. That's me just doing more homework to find out where can I show up the number?

• 16:37Harry Stebbings?

  What's a good reason for a slip deal versus a bad reason?

• 16:41Speaker 00

  There are always unnatural things that happen. I think a good reason for me is we tried to pull it forward from the next quarter. We couldn't get through all of the required steps and so it actually should have stayed in Q2 instead of Q1. That's my favorite reason. I think stuff happens, right? In sales, it's the one profession that you can try to control everything, but shit still hits the fan from time to time. So you try to control as much as you can. I can't say there's ever a good slip deal reason. I think some are just less bad.

• 17:06Harry Stebbings?

  Okay. So we have that as number one, like analysis on slip deals. Number two.

• 17:10Speaker 00

  You know, most companies are going to say, hey, leader, put in your pencil or your forecast number of what you're going to hit this quarter. What I do with this and what our best practice is, is you're looking at the actual pencil number and then you're building the commit deal back walk up, we would say. So if I'm committing a million dollars, I better have a million dollars in commit deals. One, you're counting a number, but two, you're also calling your shot on which deals are the furthest along.

• 17:31Harry Stebbings?

  Leaders often push for more. Come on, Ben, come on.

• 17:35Speaker 00

  Yeah, no, you have to push for more. I think it's week one though, right? So it's still early. You haven't done QBRs, you haven't done those things. I want that number at least to tie out. I of course want to reverse waterfall where the deal back walk up is higher than the commit and the total pipe gen, the most likely, all those fun things are better than the most likely. And then the total pipeline is killing it for the best case. Of course you want to reverse waterfall, but I think in week one, I'm pretty realistic about it because a lot of times they don't have the commit deals to actually back into the pencil and a lot of the organizations I've been.

• 18:03Harry Stebbings?

  But like, are leaders wrong to push for more? When you Ben say, hey, 1.2, am I wrong to say, come on, Ben, we can do 1.4?

• 18:11Speaker 00

  I think the best leaders don't believe the stories that they tell. Every QBR I've ever been to, every AE puts up a slide that says, here's me finishing at 120% plan. Every time it's magical. Now, do 100% of AEs finish at 120% plan? Never. The best sales leaders I've been around, the people that I've learned the most from is yes, you push them to tell more, but you're really realistic and honest on the state of the business. And that requires kind of the 13 week process to make sure that you're checking and understanding where the holes in your business are.

• 18:39Harry Stebbings?

  Okay. So number two, we've got put down your numbers, sales leader. What's number three? This is so good, by the way.

• 18:44Speaker 00

  Number three in week one for us actually is we actually look at renewals a quarter out. So we found we need roughly three to six months to move the needle significantly on a renewal on either retention, churn or upsell. So we actually are looking at that in week one on our dashboard as well.

• 19:01Harry Stebbings?

  What does that involve?

• 19:02Speaker 00

  So for us, the way you look at it, and depending on the business, right? You probably have telemetry on your adoption and usage data. You of course have the contract amount, when it's coming up for renewal and you're cross referencing those two things to say, hey, if this person is bad telemetry or bad adoption usage and a big contract, I'm going to prioritize those discussions.

• 19:20Harry Stebbings?

  Prioritizing those discussions, then then we just put more CSMs on it. We give them more love. What do we do?

• 19:27Speaker 00

  I think you're understanding the risk in week one for us. Yes, eventually you're likely swarming around it, but I think for me, it's as simple as, hey, let me look a quarter ahead. Do we have any glaring mistakes? And it's probably 5% of the forecast call, but holy cow, it's a new quarter. Let's start a new, let's get a sprint call related to this or a big deal review or whatever you want to call it to get the team on the horn. Cause one of our top 10 renewals is at risk and let's deal with it now instead of 90 days from now. So that's probably the step on that. And then step four is basic of like, let me look at my overall pipe coverage. And you're looking at that based on historical conversion rates from various stages. And that's where I think from us, our tooling comes in more to say, hey, the predictive forecasting, the ML is going to tell you, you're going to land at this

• 20:09Speaker 00

  based on where the pipeline sits today across early stage, mid-stage, late-stage. And once you have those four things, like that's week one and we can go through the whole thing. But it later just turns into more of like, how do you then look at conversion of pipeline? And then in the last couple of weeks, of course, it's just purely execution of are we doing the right things to make sure we're moving the needle in as short as timeframe as possible?

• 20:29Harry Stebbings?

  It is amazing to be as granular as this because so many founders will literally be pausing and taking notes on it. And so my question to you is like, should we go through week two now? Or are there elements where you're like, this is a cool milestone point? This is a cool milestone point. Focus on those.

• 20:42Speaker 00

  For me, we chunk it into four chunks. So what we did is actually, and my SVP of RevOps, Scott Peiser, he helped kind of document all this. And we realized it was to tighten up our own forecast cadence. And then we were like, holy cow, we're on to something and clients should be able to have access to this too. So a lot of times we're giving it to them or we're just mapping back based on their individual business needs or revenue objectives. The way I think about it is based on the individual week and there's different widgets or different pieces of the dashboard. But it's, you're looking at four different aspects of the business. So one, and I will use a cheesy alliteration to make it easier to follow, but we think about it as like, and depending on the week, you're going deeper or less deep into each of them. So you can imagine in week one, like we just talked about, create is kind of the most important piece of this of looking at pipe gen efforts.

• 21:27Speaker 00

  Do I have enough pipe coverage? All the things we talked Talked about, but like the last piece of it is what's my pipe coverage? What's my historical pipe coverage? What's my historical pipe by stage same time last quarter, same time last quarter, last year, those types of things where you're really trying to understand the help of your business. I think convert week six, I'm looking at stalled pipe. I'm looking at pipe that's been in a certain stage for a certain amount of dates. I'm looking at all those things of like where in the med pick questions do I have holes? Close, right? Of course, is the last three weeks of like just making sure what deals are in commit that haven't talked about budget, don't have MSA sign, haven't exchanged files, aren't at the right level from the key stakeholders or shareholders, whatever it may be. And then churn is the dreaded C where you're looking at throughout the time. And software, you can't do unnatural acts typically to get you to renew in less than,

• 22:12Speaker 00

  call it three to six months. So you're always looking Q plus one plus two and looking for the route depending on the week and when you have more time to be really, really smart about seeing around corners.

• 22:22Harry Stebbings?

  So we've got create, convert,

• 22:24Speaker 00

  Close and churn.

• 22:25Harry Stebbings?

  What's core to doing convert? Well,

• 22:28Speaker 00

  So one, you have all the stats to say where our deal stalled and some of that can be CRM hygiene. Hopefully that's what it is and it's not lack of operational rigor. I think where we see a lot of this is one, we use med pick internally and making sure we're asking the right questions on a forecast call. And the interesting thing we deployed is actually all my leaders now record their forecast calls. I listen to the smart summary Sunday night. So instead of going to the forecast call to say, hey, we still good on that deal. It's I know my enterprise sales leader has risk on three of her five top deals. I know her number. I'm going to dig in specifically on the three areas that those deals are stalled. Maybe it's legal, maybe it's security, maybe it's we haven't built the right champions, whatever it is. But I think what's your aggregating those pieces in the convert part of the bulk of the quarter in the heavy

• 23:10Speaker 00

  middle, you are absolutely focused on where the holes of these deals and not to beat the beat people up, but more specifically like, how do we get the weight of the company behind whatever they need to help close that deal?

• 23:21Harry Stebbings?

  What tools and processes do you use in the convert phase to move deals down pipe?

• 23:25Speaker 00

  Clary for me as a forecasting platform is as a CRO, you have a gun to your head every day. You don't have enough hours in the time and as a founder, you feel the same way. So all I need is give me the signal to where the gap in my business is. And a lot of times it's on the career or on the convert side to your point. So if I then go into the convert, I can look at call recordings. I can look at sales engagement. I can look at med pick questions. I can dig into the deal review to say, hey, these ones are stalled or at risk. Cause hopefully Clary is saying, look, these are the five that are not going to close. And then I know where to go. And then your job as a sales leader is pretty natural. I think for most people to help understand where that deal is at, how you can help and then move on from there. So that's one, the tooling, two, the process to just make sure stuff doesn't fall through the gaps. But ultimately it's just to try to focus your time for the signal to noise.

• 24:11Harry Stebbings?

  How do you advise founders on leveraging the team to work more together to close a deal? What do you do in those cases? Is it ever like Ben, you went to, you know, Wisconsin, this guy's a Wisconsin guy. Like come in on this call, talk about Scanny and just build that rapport. So it's a little bit more natural. Is that it?

• 24:29Speaker 00

  So I think it's really hard to get a team to work together well in a deal. That isn't a good team to begin with. And this may be too ethereal, but I think about it more of like, hopefully you've built great cross functional relationships. And my job as a CRO to be tight with product, tight with marketing, tight with the CEO and have those open and honest relationships. So it isn't, hey, this is what I need specifically for this deal for Harry. It is more a natural thing that always happens of, hey, this one might need a product roadmap. This one might need some marketing love. This one might need whatever, like if you don't have that trust and that foundation set up upfront, it's really hard and it's really obvious. And there's the jokes we've all made of when certain sales teams show up with 16 people in the room. It's because they don't work as a fricking team, right? And those that do can show up with three and say, yeah, we got each other's backs and we can interchange roles.

• 25:14Speaker 00

  So I think I take it back a step further of like, I think my job as a CRO is to kind of be the glue for the company, for the customer facing efforts to make sure we are one unified front.

• 25:23Harry Stebbings?

  Convert, I have so many where I'm on the board of them. They're like, yeah, you know, honestly, they just said it slipped to next quarter. They love us, they love us, Ben, but it just slipped to next quarter. How do you respond when someone in your team says that?

• 25:35Speaker 00

  I hopefully at that point, you've gone through like, who's the decision maker? What is their decision criteria? What was the compelling event? Is this budget in funded? The traditional med pick questions. And you'll know pretty quick digging into one quick one on one with a seller. Like if they actually did their homework or if they just trusted their champion. And they do have a great relationship, but they didn't actually help them sell internally. I think there's a reason all these sales methodology exist. It's because if you do the homework nine times out of ten, it does work. And I think a lot of it is just doing the right research and asking the right questions.

• 26:04Harry Stebbings?

  What are the biggest reasons deals don't close?

• 26:07Speaker 00

  Candidly, is you don't understand the client's buying process. And why I say that is usually the deals that don't close are the deals that are commit that are the ones that are most painful. Where, hey, we're 75% likely to be chosen. We're the vendor of choice, whatever it may be. Like then it really is just a process problem that you didn't truly understand what that person had to do internally. But I think specifically for me, the most painful ones are the commit, which is I think coming back to not understanding the buyer's internal processes to get things done.

• 26:35Harry Stebbings?

  Talk to me about churn. When you look at this, the hardest thing is also the relationship between CS and sales. We do the close three and then we think about four churn. And often it's because I close ban and then I throw you over to, you know, whatever on CS and it's like a terrible handoff. How do we think about creating great interplay between sales and CS to make sure implementation, adoption is great?

• 26:58Speaker 00

  Back to your earlier question, a lot of it has, has to do with selling the right way. So if you're selling the right way and it looking at the deal construction, looking at when someone wants to be live, truly understanding the process rather than just saying, here's a sexy widget, buy it. But you've mapped out their journey based on business impact and complexity to implement. You understand upfront in pre-sales what they're going to do and what they need to do. It's a hell of a lot easier to hand that blueprint over to customer success and have them pick it up like they've been along for the ride the whole time than if it is, hey, Harry, I have this great product that's going to solve all these issues, but we don't actually do a thorough sale. That's never going to work in general, regardless of how great your CS team is. Like you have to have a very thorough and outcome based sale, I guess, from the beginning to make sure that your customer success team is set up for success.

• 27:42Harry Stebbings?

  So we have these, but the speed of which you go through them. Is going to determine a lot and that is often determined by the size of the contract or the size of the deal.

• 27:52Speaker 00

  Yep.

• 27:52Harry Stebbings?

  I would love to discuss the kind of transition from say smaller commercial agreements to enterprise agreements, much larger deals. What are your biggest lessons in terms of what it takes to grow from smaller commercial to large enterprise accounts?

• 28:07Speaker 00

  So, and I think I was fortunate enough, like I started my career actually at Salesforce as a commercial AE and then I got fortunate enough to move to the enterprise team and become a global account manager. Honestly, I looked at actually the move from commercial to enterprise and it was funny. I sat down with my A V P at the time and he said, Ben, you got to treat this account like 80 little accounts. It's a big global conglomerate. They have multiple different P and Ls. They have multiple different regions. And if you just treat them all like little commercial accounts and do the homework for each and solve each of their problems, it'll bubble up one day and eventually you'll drive a big enterprise license agreement. So long-winded way to think for me is like, it's the same game. It is just different stakes in terms of the number of internal stakeholders and folks that you have to have your back and help you to get things done. And then obviously external stakeholders, it's a lot more complex to sell to a 300,000

• 28:52Speaker 00

  person company than a 300 person company. But I think that the process and the motion should be the same for the best companies in the world.

• 28:59Harry Stebbings?

  Can the process and motion be the same though? You're a C R O, resource allocation is one of your core roles. You cannot allocate the same resources to a 5K A C V as you can a 500K A C V. How do you think about mapping that out? And does that get more challenging in a world of P L G where all entries are probably smaller?

• 29:18Speaker 00

  That's totally fair. And I think what I meant is more the motion. So I think hopefully I'm doing a solution selling motion. I'm understanding the client's problems. I'm providing my point of view. I'm showing them how I uniquely solve it. I'm doing creative deal construction. That's a win win. If I'm in enterprise or commercial, of course, there's the complete long tail that hopefully you can set up some type of self-serve because cost of sale and all those fun things. But a hundred percent, like given the complexity of the internal stakeholders, the external stakeholders, you're going to need more people and more capacity and more yield on the biggest companies in the world, which I think is pretty common for most places. I was gonna say, how do you think about it? Like it is trial and error. I've seen so many times like your favorite. Salesperson or the loudest squeaky wheel, right? Or whatever is going to ask for the most amount of resources. And sometimes you trust it, sometimes you don't.

• 30:02Speaker 00

  I think there's a million different thoughts about how we actually resource these things correctly. And it's a lot of it is trial and error and never being too scared to be iterative of we got to change, especially at a company our size of like, we make decisions based on where we think there is the most propensity to buy. And there is the biggest opportunity, but stuff changes and things happen. And you've got to be willing to iterate and move folks around like without causing too much disruption.

• 30:25Harry Stebbings?

  How do you think about when's the right time to invest in sales enablement? It's a little bit of like an insider's game and for like product led founders, it's like sales enablement. When should they start investing in it?

• 30:35Speaker 00

  I think if you hire the right sales team, sales enablement, not that it becomes an afterthought, but I think a lot of folks think about, and I get asked this question, a lot of sales enablement. I'm like, I read something the other day that was physicians stop listening after 18 seconds. And that's not a knock on doctors. It's just like, if you talk for more than 18 seconds, people are likely tuning out. So when you do these enablement webinars and you're saying, hey, it's a mandatory two hour session every Friday. We're going to talk about product, sales process, you fall asleep. If I am a good FLN and if I am empowered and accountable to drive all of the micro moments. And we say, Harry, we just got off this call. Here's the three things you could do better. Help me understand what I could have done better, like, and actually create more of a culture of accountability and feedback.

• 31:16Speaker 00

  I have found that drives a hell of a lot more enablement in those micro moments than like the big overall SKOs, the weekly webinars, you have to do some of that, but I think it's really, really, really be measured about it. And specifically for a startup, you're probably all in the same office. You probably all talk a thousand times a day. You probably go to breakfast, lunch and dinner together. I don't think you need formal sales enablement at that point. You just need really, really, really strong sales leaders that think about accountability and enablement as part of their job.

• 31:43Harry Stebbings?

  What do you think startups get most wrong as they try and scale from smaller to larger enterprise accounts?

• 31:49Speaker 00

  I think it's a big bet, right? And at Clary, we looked at enterprise versus commercial. And I think we said, hey, we have the most sophisticated forecasting tool. So we should move more capacity into the enterprise. But it was a big strategic decision at the board level. I think a lot of folks go to enterprise because they say, hey, there's more money there. And that's always true, but I think you have to find your product niche. And the unique problems your customers have and how your product solves it is where I would spend and put my chips. And I have founder friends that are saying like, we want to be Gen AI for very small startups. We don't want to deal with the biggest companies in the world because we can't build the capacity that they have. And I think that's a very intelligent decision.

• 32:26Harry Stebbings?

  So Stevie, the CRO at Vanta is also in 20 sales. And so I work with her closely and she always says that actually you can stress test moving into enterprise more reasonably or without such investment than people think. Can you kind of dip your toe into an enterprise motion without having it be a big company wide bet?

• 32:44Speaker 00

  Yes, I think you can. And sorry, what I meant is if you're shifting your capacity to enterprise, like you better be very, very sure of it. Even the biggest tech companies in the world, when they're calling on the other biggest tech companies in the world, like you're going to have different requirements. They are a special snowflake. You're going to have to invest R and D dollars, which most startups and most earlier stage companies don't have the capacity to do on the development side. So I think to her point, it's a great one. If you test it with, hey, I'm going to go after name big company X, Y, or Z. And if it requires a huge shift in my roadmap, you're going to have to give up stuff that you were planning on developing, which I think is the hardest part for earlier stage companies.

• 33:20Harry Stebbings?

  One thing I've noticed that really increases speed is much tighter product marketing and verticalization. You're able to build a brand in a much tighter community. Can you help me out? What are some of your biggest lessons in terms of building vertical teams?

• 33:35Speaker 00

  When it comes to product marketing and messaging, and I think Salesforce is the absolute master at this. If I talk about bits and bytes and features and functions that aren't relative to your individual problem, like you're going to lose. I think for us, when we talk to med device companies, we show up and talk about forecasting the way of create, convert, close and churn. And they're like, we're a consumable company. So we had to relearn how to actually talk to med device companies. And really understand like, oh, okay, like you're not forecasting in the way that we are in terms of true B to B opportunities. You're actually forecasting in how many syringes or how many whatever they're going to go through on a daily basis. How do we reframe this and help you track that in a more accurate way? So extremely long way of saying, talk the language of your client, understand their unique problems and how you can uniquely solve them.

• 34:20Speaker 00

  And sometimes you can't, right? And I think for earlier stage companies a little bit is, yeah, it's always fun to go after the JPMC's, the bank Morgan's, the biggest banks in the world. But sometimes you're not a good fit. So play where you fit well. And that's been, I think, a big thing I've learned through the last three steps.

• 34:34Harry Stebbings?

  How early can you verticalize? Is it only when you're huge or what's the lesson on timing?

• 34:40Speaker 00

  This is a great debate that I've had many, many times as I verticalize teams. I think unless you have a verticalized product, it does cost money, right? And I remember a Salesforce exec, head of sales telling me, we started healthcare. He's like, I'm expecting you guys to actually shrink this year and then grow exponentially. But it costs money and it is an investment because it is harder to scale across a bigger geography. So I think you have to be willing to take that if you're a certain size company.

• 35:07Harry Stebbings?

  I don't understand why it's harder, like product marketing is easier, word of mouth is quicker, product resonance is better. Your understanding of the customer is better. Why is it slower?

• 35:17Speaker 00

  I wouldn't say it's slower and I'm a violent proponent of verticals. I think folks would just say it's more expensive because I can't take a banking expert and put them into healthcare. And there's not as much abilities that are designated hitters or can play every position on the field. Like your CSM team has to understand it, your SE team has to understand it, your AE team has to. So there is an added investment there. Plus you're specializing your messaging versus if you have a broad based message that applies to everybody. It's a little bit easier from a product marketing perspective, but I violently agree with you. I think when I look at the CROs I talk to, those that have sound vertical strategies are the ones that are feeling the least amount of pain throughout this macro climate. Because I think they have it nailed and I think those with vertical approaches are actually winning right now.

• 36:01Harry Stebbings?

  Who do you think has the best vertical sales strategy today?

• 36:04Speaker 00

  I'd ask you that first. I think you talk to a lot of folks.

• 36:07Harry Stebbings?

  I would actually say a company that we just invested in. Actually, it's this German business called ALO and it basically takes on light speed and toast for payments providers for restaurants. And they have a vertical sales strategy for ethnic restaurants. Ethnic restaurants are basically anything that's not your domestic restaurant. But they have a vertical sales strategy where they send in a Chinese person into Chinese restaurants. A Taiwanese person is Taiwanese. Why? Because people want to buy from people who are like them. And when you're in a neutral slash foreign country like Germany or Italy or France or Spain. A Chinese person or an Italian person will instantly have so much more engagement. When that person comes in speaking their language, instantly you are nine out of 10.

• 36:49Speaker 00

  That's fascinating business concept, by the way, and good investment on you. So I think a lot of folks that have the dedicated vertical strategies and specifically vertical solutions are the ones that are persevering the best, I should say, with the macroeconomic conditions.

• 37:01Harry Stebbings?

  I actually think you should do it as soon as possible. I think people, if they're good, can learn verticals pretty quickly. You learn by speaking to people, by doing that customer qualification. And actually, you can dip your toe in the water too, in the couple of core verticals. And so I think do it as early as possible. We've spoken a lot about the process and everything that's involved. We've kind of jumped the step of you actually need good people to make all of that happen. Just in terms of hiring, I want this to be like a coffee where you're advising me. How do I hire great salespeople?

• 37:32Speaker 00

  I think for me, how I think about salespeople and another cheesy alliteration, I think about it through three lenses. Attitude, aptitude and authenticity. And they all kind of mean a little bit of different thing, but I think those are the three things that I care the most about. I care less about experience. I care less about the Rolodex. I care attitude. In any sales organization, you're going to have problems and you look at them as opportunities.

• 37:53Harry Stebbings?

  How do you test for attitude?

• 37:54Speaker 00

  I think two things. My favorite interview question is somewhat testing for growth mindset. And what we should ask this for the podcast, Harry, you've been wildly successful. What's the number one reason you haven't had more success? So most salespeople will say, I didn't have the right territory. My quota was too big. I didn't have a product that customers resonated with. You're immediately not hired. If you say, I honestly have had struggled with X, Y or Z, or I'm really working on X, Y or Z. Know you probably have a growth mindset that you're self-aware enough to know that you're not perfect.

• 38:24Harry Stebbings?

  What percent of the time do people say something that's self-aware about themselves versus it was actually the segment? It was the price, it was that.

• 38:32Speaker 00

  Surprisingly enough, it's probably sixty to seventy percent of the time. Salespeople will say something that was outside of their control.

• 38:40Harry Stebbings?

  Wow, okay, so that's a quick disqualification.

• 38:42Speaker 00

  Yeah.

• 38:42Harry Stebbings?

  Okay, so we have attitude there with that. Any other questions to test for attitude?

• 38:46Speaker 00

  You can tell them, folks, like, yes, you're boasting about yourself a little bit on an interview. But I think the other piece on attitude is how curious are they about the company? And nine times out of ten with like, I'm brutally honest and not a sales pitch, but I'm saying, hey, here's all of our awards. And you'll tell really quickly of like, they scared and they they want to have a perfect quota and a perfect territory to jump into. Or are they looking at it as an opportunity and things I can actually change and I can stand out with whatever problems they may have?

• 39:10Harry Stebbings?

  It's similar for me when investing. I to test attitude, I always want to see an entrepreneurial mindset super early because it's the biggest correlation with future success. So I always say, how did you first make money? And there's two answers. One is I started selling T-shirts when I was at university and no joke aside, and it happened and I learned this. And the other is, oh, I came out of Cambridge and then I went to McKinsey.

• 39:30Speaker 00

  Yeah.

• 39:31Harry Stebbings?

  Big difference in terms of the attitude early. Okay, so we have that in terms of attitude, aptitude. What are we looking for here?

• 39:37Speaker 00

  Yeah, aptitude, I think, is are you intellectually curious? This you can figure out really quickly in an interview too. One, it's amazing to me how many candidates don't ask questions or they ask, hey, what are the next steps in the process? And they don't come like, this is your one time to interview me too, right? And interview our company and make sure you're pushing there.

• 39:52Harry Stebbings?

  What questions should candidates ask? Are there any, generally speaking, that you should ask?

• 39:58Speaker 00

  I did this the other day. I went on ChatGPT and I said, what are the most popular questions? And it's amazing to me how many people do the same thing and they ask those questions. So I'm not going to answer that. I think the thing is, is like, you should ask genuinely what you're concerned about and what you authentically care about. Salespeople need to be authentic to connect with the person on the other end of the line. If they're not sharing what they really care about in that interview and they're asking like, what do you think the biggest growth lever is for Clary? Like, shut up. No one cares at that point, right? Like, let's be honest, if you say, hey, my favorite interview question I ask all the time, like, Harry. What's the one thing you change about your company? Nine times out of 10, you'll catch people flat footed and they'll share their real opinion about what they care. I think to me, on the intellectual curiosity side, you have to have it on your product. You have to have it on your space. You have to have it on your customer. And you have to be authentic about it is the last A.

• 40:42Speaker 00

  And if you're not showing up in that interview process saying like, hey, I really need this amount of, I don't care what the question is, ask what's authentically you.

• 40:49Harry Stebbings?

  Is it challenging when you have a candidate who's just purely money motivated? If you rock up and I'm like, Ben, listen, I'm not lying to you, honest. I don't really give a shit about forecasting. I will close dollars and I'm a machine at closing. I love the sales game. Now you can sell, I can sell anything.

• 41:05Speaker 00

  If they check all the other boxes, I have no problem if money is your number one motivation. And I think most sellers try to hide it and there's nothing wrong with that. And as long as you're authentic about what your reasons are, it helps me understand, A, how you're going to potentially fit in the culture and B, how I can help you stay motivated.

• 41:22Harry Stebbings?

  The lucky thing is venture capitalists aren't money motivated, so I don't have that often.

• 41:27Speaker 00

  Heard that about you all.

• 41:28Harry Stebbings?

  What's the best question you've been asked by a candidate?

• 41:31Speaker 00

  My favorite question in almost every conversation I have is, is there anything that I didn't ask you that I should have? And that's a good catch all for the end of an interview. I think that a lot of times will get me to say, yeah, or no, right? Like it's, it's kind of a soft close before the close. So that's a question I think I ask a lot of clients at the, almost the end of every client conversation. And I think the same thing for interviews too.

• 41:52Harry Stebbings?

  What skill that you're slightly cautious to admit has been the biggest contributor to your success?

• 41:58Speaker 00

  Two things that I think a lot about. I think one earlier on my career was the fear of failure for sure. Like I was very much motivated to say, I can't lose at anything and I'm going to outwork, out hustle, do everything within my power to make sure I don't lose. I was talking to someone, actually our CEO the other day about this of like on a bike, if you tried to pass me in a bike when I was 30, 10 years ago, I would throw up trying to pass you. I couldn't let it happen. I was that competitive in everything I did or ping pong or silly things. And I think that was a big thing for a while. And there's a motivation there that's like a competitive drive. And then the second piece I think is like, I don't want to let people down. I think one that's hopefully made me be a great or decent people leader, I should say. But also like the impact you're going to.

• 42:39Speaker 00

  Hopefully have with clients. If you think that lens of like, I want to make sure they walk away from this in a healthy spot. Is another thing that I'm somewhat embarrassed about because I don't want to be like a people pleaser. I don't want to be that person and say that I'm like so insecure that I'm always worried about how people think about me. But I think a lot of times it is, I really, really don't want to let people down. I don't want them leaving with a great taste in their mouth regardless of any conversation, interaction, purchase, whatever it may be.

• 43:05Harry Stebbings?

  Listen, I can do feedback review. I think from all the conversations I had before, your biggest strength is your biggest weakness, which is like your authenticity and kindness. Leads you to build very real relationships, but actually it means you delay some hard decisions and struggle with doing those discussions. Because of the authenticity and kind of kindness. It's like kindness is good and it's challenging as well.

• 43:27Speaker 00

  I don't know who you interviewed and who said that, but I will make sure I call them later and chastise them as a way to make sure that I, and I'm just kidding and lay into them. No, I think it's totally fair feedback. And I think it's probably the biggest development area that I have is as a sales leader, clear is kind. And I think I've gotten that. And I think I now know that like, if I'm direct with you, Harry, and I tell you exactly what you need to work on, that's actually the best thing for you. Then if I try to sugarcoat it and be nice and not be intimidated to let you down. And that's a huge thing that I've worked on, I'd say over the last three to four years.

• 43:58Harry Stebbings?

  Do we do take homes in the interview process?

• 44:01Speaker 00

  I've struggled with the role playing because I think people then overplay the acting part. And a lot of times my own team and myself don't read the prep well enough to be like, the person's actually really asking a good enough question. We're just being jerks and not playing the role of the CFO. So I got rid of the role playing. I think the thing that we do is, and that we've somewhat perfected is hopefully you come in, you're going to present an account plan or an executive point of view. So we'll pick an account that's in your patch. We'll say, come in with us. You're going to act like you're prepping your boss and your boss's boss for an executive meeting. So it's, we're playing ourselves. And you're going to help understand, A, what the executive point of view is, what their biggest challenges are, how we can uniquely solve them and how we'd approach the meeting.

• 44:39Speaker 00

  Which I think you learn a lot about how, one, salespeople prep, but B, back to the original first question you asked me, can they develop a strong executive point of view that is actually unique? Is pointed enough that is going to A get them the meeting and B help drive value for that client ultimately.

• 44:54Harry Stebbings?

  And then what's the most common reason that reps fuck up in the interview process?

• 44:59Speaker 00

  I think they're just unprepared.

• 45:00Harry Stebbings?

  Wow.

• 45:01Speaker 00

  And if you're unprepared for an interview, like, how are you going to be for a customer call?

• 45:05Harry Stebbings?

  The only thing I'd probably say is maybe they're interviewing with 10 different people. And so if they're in the role, then it may be different, but I totally agree with you.

• 45:14Speaker 00

  You know this and you've probably, I don't know how many times you've interviewed, I've interviewed for jobs, I blatantly didn't always have interest in going after. But that's your brand. Even if I didn't want that job, I better show up really, really well so that when they think about me the next time, like, I'm there. The same way with recruiters I call, I will show up prepared and have a unique point of view. I think that's just table stakes of like, the one thing you can control is your attitude and your preparation. That isn't so much to ask.

• 45:39Harry Stebbings?

  Okay. So going back, we have attitude, we have aptitude, anything else?

• 45:43Speaker 00

  Authenticity, which I think we've talked a little bit about. I think what I've found over the time is like, I've seen a lot of performative salespeople who think this is what a salesperson should act like and be like. That rarely works. To your point, there's money driven salespeople, there's salespeople you've met that are complete assholes, but they own it. As long as you're authentically yourself, people are going to connect with you more. And if you're vulnerable and open and are who you are, I think it's way easier to connect with others. And I think people want to buy from people like that.

• 46:09Harry Stebbings?

  Final element, we get to the comp plan. We're like, yep, we want to put Ben in the team. What are the biggest lessons on creating a comp package that's compelling for sales reps?

• 46:18Speaker 00

  I think where we've looked at this and an example from Clary, like we had hunter farmer sellers. And then we moved to a hybrid for the enterprise team, meaning they had both install base and that new logos. I think so often comp plans are designed after the fact. I think the only big lesson that I'd have is like, you need to decide your go to market strategy. And yes, that's going to have inputs from finance on margin targets, profit targets, growth targets, all of those things. Design your sales alignment, design your sales motion, and then the comp plan should come after that to reinforce those things. I think too often it's backed into of like, well, this is what we did last year. Let's make a small tweak versus holistically taking a step back and looking at the overall go to market strategy.

• 46:58Speaker 00

  Alignment, motion, talent, and what you're trying to drive and use those design principles to design the comp plan.

• 47:04Harry Stebbings?

  You said before there about the hunter farmer. I'm just intrigued. I had Dave Kellogg, who I love as a guest on before. And he's like, you never want to have your farmer against someone else's hunter. How do you prevent that?

• 47:17Speaker 00

  By the way, I love him too. And his, I forget, he had a blog recently that like six bullets, I shared it with my, like, the greatest career advice. I'm like, holy shit, is he good? Share it with all my leadership team. The question, how do you make sure your hunter doesn't go up against your farmer or up against someone's farmer? I think you have to choose your segments really, really intelligently. Back to your earlier question about where do you put capacity, where it's going to drive the biggest yield? For us, that was a move to enterprise and we got very, very specific of our enterprise AEs at 100 accounts in their territory. We're like, that's never going to work. Let's be super smart about the ones we have to win and let's overstaff those. So hopefully if you know your ICP, you know your unique sol that you have for that client base, you're going to put people in the right space and then you're not going to run into that.

• 48:00Speaker 00

  But it's going to happen probably in longer tail businesses all the time.

• 48:03Harry Stebbings?

  I want to move into a quick fire. So I say a short statement, you give me your immediate thoughts. Does that sound okay?

• 48:08Speaker 00

  This is a lightning round. I'd love it.

• 48:10Harry Stebbings?

  What sales tactic has died a death?

• 48:13Speaker 00

  The pricing expires at the end of this month or end of this quarter. Used car salesman of like, this deal turns into a pumpkin on October 31st. I think people will call bullshit every time on that.

• 48:23Harry Stebbings?

  What about, hey, we take our big customers to a box at Taylor Swift. We do big golf days. Does that still a thing?

• 48:30Speaker 00

  Not always for my beer budget and champagne tastes, but I mean Salesforce still sponsors you. There's Formula One and I buy all the looks of it. There's lots of people were near you last weekend having a great time.

• 48:41Harry Stebbings?

  What's the biggest lesson from UiPath?

• 48:43Speaker 00

  Be extremely intelligent and design your sales team based on product market fit.

• 48:48Harry Stebbings?

  Unpack that.

• 48:49Speaker 00

  When I joined UiPath, we were designing geographies and I had the pleasure of running their key accounts program, which call it their top 100 accounts. I had banking and healthcare clients, so the JPMC's, the HCA's, the Signas of the world. We saw an absolute disproportionate amount of opportunity and we hadn't planned our capacity for that. We had peanut butter spread everything geography wise. And we said, holy cow, even though healthcare and banking are our biggest baselines, it's also our biggest potential opportunity because of how our technology at the time fit in with the problems that they had. And I think as a second line leader at the time, I've made the call to help push all the chips in from my perspective, but build a coalition. Around me and it certainly wasn't my own doing, but it was one of those things of like, holy cow, we have a unique product market fit.

• 49:32Speaker 00

  To your point, don't be scared of verticals, don't not dip your toe in. And we made the bet in a big, big way and it paid off. That was one where there's been plenty of times in my career where I've seen something work, but it's like, oh, that might've been an anomaly. That might've been an exception. And in that case, it was holy shit, this is really working and we got to push all our chips in and the company rallied around it and did it.

• 49:53Harry Stebbings?

  What are the biggest reasons CROs and heads of sales fall out?

• 49:57Speaker 00

  I think too often they come in with design playbooks or this worked at this company and blah, blah, blah. And I'm going to copy and paste it here instead of coming in with design principles about these are the things that I know and the frameworks that I can apply. But I'm really going to listen to the needs of this individual company or this individual sales team and what they need and design a playbook that works for them. I think a lot of times I talk to CROs that are saying, well, I did it at this company. Why doesn't it work here? And every company is different challenges. Everybody has different, unique parts of their maturity journey. And like, you gotta be really, really smart about solving the problems that that company has versus bringing your old playbook to the new company.

• 50:36Harry Stebbings?

  What do you know now that you wish you'd known when you entered sales way, way back with Salesforce?

• 50:41Speaker 00

  It was funny, there was an exec at Salesforce that I think I thought I had to be something I wasn't because the Salesforce model was very, very uniform at the time. And he pulled me aside and just said, dude, be yourself. Like, don't get in your thoughts, don't try to replicate what this person does, don't be that personality. Like, just be yourself, be authentically you. And that was the biggest unlock, I think, for my career of not everybody's the big performer, not everybody's the gregarious relationship person. Not everyone's the really data-driven, ROI-specific, detail-oriented seller. And I think you have to play to your strengths rather than trying to be something you're not.

• 51:18Harry Stebbings?

  Ben, what question did I not ask you that I should have asked?

• 51:21Speaker 00

  Uh, well played, Harry. Well played.

• 51:24Harry Stebbings?

  I've done 3,000. Like, you, you get relatively good at this.

• 51:27Speaker 00

  You've done 3,000 podcasts? Holy cow.

• 51:30Harry Stebbings?

  I'm not that young anymore.

• 51:31Speaker 00

  I think you're pretty young, based on the bio I've read. You look great.

• 51:34Harry Stebbings?

  Thanks, dude.

• 51:35Speaker 00

  Zoom filters work well.

• 51:36Harry Stebbings?

  What is the secret to a happy marriage?

• 51:39Speaker 00

  Aptitude, attitude and authenticity.

• 51:41Harry Stebbings?

  Same.

• 51:42Speaker 00

  The biggest thing I would say on marriage is be authentically you and share exactly what your feelings are at. I think as I've gotten older, I've spent a lot more time investing in the marriage as much as I have in my career.

• 51:54Harry Stebbings?

  How do you invest more in a marriage? That's like date night? What does that mean?

• 51:57Speaker 00

  Yeah. No, I think it, look, how many CROs I talked to, if their CEO called, they immediately would be like, Harry, hang on one second, I gotta take this. If your wife calls, how many people do I know that do that? Very few. In certain high-powered positions. So I think it's one thing of like, be honest with yourself of where your priorities are at, and actually put the parameters in place to make sure you're prioritizing your spouse, your kids, your partner, whatever it may be. And I think put the same effort into it, the same way where a lot of times, like, you know, you're on the road for two straight weeks, you get home Friday night, the first thing you want to do is have a glass of wine and just sink into the couch. You gotta show up the same way you did for the client at 8 a.m. as you did for your kids at 6 p.m. And I think that's probably a lesson that I've had in the last five years. It took me a long time to, to make sure that I was putting as much effort into my personal life as I was my professional life.

• 52:42Harry Stebbings?

  That's hard. That's really hard.

• 52:43Speaker 00

  What's funny is I started my career in General Electric, and I remember we had a roundtable, and it was the same thing back to the interview questions of like, people asking questions like, what's the biggest growth level for GE Capital? And ML, there's 12 of us in the room, stopped. He's like, why is it one of you asked me like, how often do I see my kids? And he goes candidly, and this was kind of ways into your point, he's like, if you want my job, I schedule time and outlook with my kids. I'm on a private jet. Yeah, it's awesome, but I'm on a jet 272 days a year. So you all want my job, like, that is the reality of what you had to face. Now, that was circa early 2000s, late 90s. So I hope it's changed a little bit with the world of Zoom. And I, I, I do think like, look, the nice thing about being in sales is you do own more of your calendar.

• 53:23Speaker 00

  I am at home taking this call. I can hang out with my kids for 30 minutes at 5 to 6 o'clock and jump back on later. So you have more flexibility in this day and age.

• 53:32Harry Stebbings?

  Ben, listen, I've loved doing this. Thank you so much for putting up with me and my wayward questions, but seriously, you've been fantastic.

• 53:38Speaker 00

  Harry, it was a pleasure, and I'm super happy that we had the time to do this.

• 53:43Harry Stebbings?

  I just love doing that show with Ben. I started these vertical shows because I wanted to give the most granular tactical advice to founders to really implement in your business. I think we did that with the Framework Illustrated today. And you can watch the full episode on YouTube by searching for 20VC. That's two zero VC. But before we leave you today, we need to talk about our sponsor for the day, Clari. Clari is an industry-leading AI-powered revenue platform that is purpose-built to help companies optimize their end-to-end revenue process. With over $4 trillion in revenue under management, Clari's customers have a material advantage to optimize their enterprise revenue process across all teams, from rep to the boardroom, by leveraging the world's largest and fastest-growing AI reservoir of enterprise revenue expertise.

• 54:27Harry Stebbings?

  More than 1,500 organizations, including Okta, Adobe, Workday, Zoom and Finextra, run revenue on Clari to improve win rates, prevent slip deals, forecast with accuracy and boost the productivity of all revenue-critical employees. To learn more about how you can create, convert and close revenue with Clari, visit clari.com. As always, I so appreciate all your support and stay tuned for an incredible 20VC episode coming this Monday with David Khan, partner at Sequoia.