Ben Fiechtner: 12-Week Step-by-Step Framework to Crush Every Sales Quarter | E1185

1. 0:00 – 0:40

   Intro

   1. BFBen Fiechtner0:00

      You're looking at four different aspects of the business. We think about it as, like, create, convert, close, and churn. 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.

   2. HSHarry Stebbings0:11

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

   3. BFBen Fiechtner0:34

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

2. 0:40 – 3:15

   The T-Shirt Business in College

   1. BFBen Fiechtner0:40

   2. HSHarry Stebbings0:40

      As I said to you before, this isn't your first time on the big screen 'cause 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, Ben, as a starting point.

   3. BFBen Fiechtner0:53

      My freshman year, uh, 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. And it 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 and went like, "We should start a T-shirt company." There was this word Sconnie, which is kind of the equivalent of Cheesehead 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 300 bucks in our, out of our own money and, like, sold out of T-shirts in probably two days. And at that point, we're like, "Holy cow, we're onto something." We set up an e-commerce website, 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. So, pretty wild.

   4. HSHarry Stebbings1:47

      Whoa, whoa, whoa, whoa, whoa, whoa, whoa. I didn't realize that th- this actually worked. No offense.

   5. BFBen Fiechtner1:50

      (laughs)

   6. HSHarry Stebbings1:50

      I thought it was, like, one of those (laughs) that, like, pff, pff, pff, you know, crashed and burned. Okay.

   7. BFBen Fiechtner1:54

      (laughs)

   8. HSHarry Stebbings1:54

      So it, it's still running today and Troy still runs it today?

   9. BFBen Fiechtner1:57

      Yeah, yeah. So there, and there's a bar now across the s- street from the stadium. There's a microbrew, like, beer that's sold throughout the Midwest. Yes. And, and a lot of it, what happened was it was actually, like, one of the most unbelievable experiences, I think, for both Troy and I. And I don't wanna speak for him, but, like, you know, I thought I was gonna go into politics, I was gonna 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 this sales thing. This is much more for me and more my speed." Um, 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, it was, I mean, over our four years, it was insanely, insanely, um, successful, I would guess and 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 inventory, shipped it out for us. So we just kinda 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.

   10. HSHarry Stebbings2:54

       I'm a little bit embarrassed now.

   11. BFBen Fiechtner2:56

       (laughs)

   12. HSHarry Stebbings2:56

       I didn't realize it was quite that successful. You shouldn't be... This is great. Did you keep the equity?

   13. BFBen Fiechtner3:01

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

3. 3:15 – 4:38

   Discovering a Love for Sales

   1. BFBen Fiechtner3:15

      days.

   2. HSHarry Stebbings3:16

      Well, that's amazing. And so w- 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?

   3. BFBen Fiechtner3:24

      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, 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 'cause I knew he would actually pay even though I had 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 have you made?" I'm like, "$72." He's like, "I gotta go back to an office to make more money and work more hours. You found a hack," right?

   4. HSHarry Stebbings3:52

      (laughs)

   5. BFBen Fiechtner3:52

      So that was one, that it was, like, kinda steered me away from it. And two, what I realized about what I wanted to do for that profession, not that I loved arguing, but I loved sharing points of view and loved trying to help people see things that maybe they hadn't seen clearly, which was debate and politics and law for me. Which then when we won our first deal with the university bookstore, it was kinda helping them to see a completely different market that they hadn't had 'cause 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 the long time. It was the exact same print for 100 years. So, 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.

4. 4:38 – 6:17

   Key Lessons in Persuading Customers

   1. BFBen Fiechtner4:38

   2. HSHarry Stebbings4:38

      It's so funny there 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?

   3. BFBen Fiechtner5:00

      The majority of organizations I've gone, 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, 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."... you may not always win, but you have a disproportional 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 wanna 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 when 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've got to know someone, you do your homework, right? And show up with a- a- a executive point of view, if

5. 6:17 – 9:45

   The Skills Behind Effective Deal Construction

   1. BFBen Fiechtner6:17

      you will.

   2. HSHarry Stebbings6:17

      One of the things that someone said was a superpower of yours, was creativity when it comes to deal construction. I wanna get it right. They said, "When it comes to deal construction, you're one of the best in the world. Uh, 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?

   3. BFBen Fiechtner6:39

      I don't know who taught me this, and I think a li- or a lot of great mentors probably at Salesforce that- that leaned into this, where a lot of times they, like, um, one of my first great bosses for a long, long time, Eric insiders, where he was like, "You own pricing." I'm like, "No, I don't. Like, I have to go through all the approvals, I have to ask for this person and this person to 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, 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 price per- like, discount percentage. Do you wanna buy?" Versus truly understanding budgets as it relates to operating expenses, cash flow, CapEx, everything, being able to note that up front.

   4. HSHarry Stebbings7:47

      What questions do you ask to understand that? Imagine I'm an angel investment of yours-

   5. BFBen Fiechtner7:51

      Yeah.

   6. HSHarry Stebbings7:51

      ... and I'm a great product founder.

   7. BFBen Fiechtner7:53

      Yeah.

   8. HSHarry Stebbings7:54

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

   9. BFBen Fiechtner7:58

      Yeah.

   10. HSHarry Stebbings7:59

       What questions do I ask to find that out?

   11. BFBen Fiechtner8:01

       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 at it, what- how do you wanna buy? I'm not gonna force you on how many users, how many of those things. Like, let's just understand your deployment schedule, what you wanna 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 and discovering that as they go. The second piece of that then is, look, as we look at this, here's my levers, it's how I've always negotiated. It's usually server start date, right? Commercial terms, length of contract. Those things are the biggest levers for traditional SaaS companies. I'm gonna tell you about those immediately. Where do you have flexibility? 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.

   12. HSHarry Stebbings8:57

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

   13. BFBen Fiechtner9:01

       Without giving too many secrets about how to negotiate with Clari on the most popular sales podcast, um, I, look, 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 gonna get, and that is true for every named user company. Same thing on consumption. The more you're going to commit to, the better break 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, um, 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 then the third thing is, like, length of contract. Fourth thing is always probably terms and conditions of simple things, payment terms, whatever it may be, and creativitive- creativity around Ts and

6. 9:45 – 14:36

   Strategies for Effective Pricing & Discounting

   1. BFBen Fiechtner9:45

      Cs.

   2. HSHarry Stebbings9:45

      Okay. What about pricing? Like, how often- how do you think about discounting? A lot of sales leaders, it's- it's so interesting. Some weaponize it and some are like, "No."

   3. BFBen Fiechtner9:54

      Like, a lot depends on the maturity of your sales team. Uh, 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- 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 guiderails, we're gonna give you the pricing you need. Um, and I- I think that's ever true now where we look at macro, econr- economic environment, SaaS going in the tank. Like, we gotta 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 'cause they were tight, but we knew it was going to be a long-term contract and was gonna help them. 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.

   4. HSHarry Stebbings10:46

      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 just- just can't get urgency in the sales cycle." Any tips there?

   5. BFBen Fiechtner10:57

      I think beyond the traditional, let's drive a compelling event, right? Of working backwards and figuring out something that it's gonna 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, and 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 gonna 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.

   6. HSHarry Stebbings11:41

      Do you go for multiple champions in a sales process? And if so, how?

   7. NANarrator11:48

      ... typically-

   8. HSHarry Stebbings11:48

      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."

   9. BFBen Fiechtner11:55

      (laughs)

   10. HSHarry Stebbings11:55

       "In which case, I want to c- close this deal." (laughs)

   11. BFBen Fiechtner11:58

       Yeah, and I think ... So 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 gotta talk to the CFO as well, and I gotta make sure that I understand his or her constraints to, 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 gonna smell right through it, and h- 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. 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 ten, it worked.

   12. HSHarry Stebbings12:52

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

   13. BFBen Fiechtner13:02

       Deferring payment terms for a terrible long time because someone is in a tight cash position usually ends poorly.

   14. HSHarry Stebbings13:09

       Mm-hmm.

   15. BFBen Fiechtner13:09

       You gotta make those bets really, really intelligently, right? Um, and I've done that, and I know people who've 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 expe- 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.

   16. HSHarry Stebbings13:34

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

   17. BFBen Fiechtner13:41

       It's funny. So most of the CFOs I talk to are like, "We're spending the same, we're just spending it on different things." Um, 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 gotta mention it ten times on every podcast we're on, right? But, um, you're seeing people shift money there and spend more money there, and that, that i- does get exceptionally expensive in certain spots. But I don't, 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 a platform-based approach, and it's been more platforms that have proven success, rather than just the shiny object. 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,

7. 14:36 – 16:49

   Accurate Forecasting in Volatile Times

   1. BFBen Fiechtner14:36

      you're getting cut.

   2. HSHarry Stebbings14:37

      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%-

   3. BFBen Fiechtner14:48

      Yeah. Yeah.

   4. HSHarry Stebbings14:48

      ... and it was a great business. But now, the accuracy of forecasting is so hard.

   5. BFBen Fiechtner14:53

      Yeah.

   6. HSHarry Stebbings14:53

      For me as a founder, how do you advise me on how to forecast accurately in a time of volatility?

   7. BFBen Fiechtner14:58

      I think three things. One, how do you drive the most simplistic process of ... I, I, 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 still good?" And we're like, "Yup." That's their forecast call. Versus I think where we looked at this at UiPath and then again at Clari was, how do I drive a 13-week revenue cadence for the quarter that I'm gonna actually chunk up into different, like four segments? 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 log-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 then as a senior leader, you have the opportunity to, 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.

   8. HSHarry Stebbings16:24

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

   9. BFBen Fiechtner16:31

      So week one, right, the first week of the quarter, um, typically, I'm looking up how ... 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 were 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 shrink the number?

8. 16:49 – 25:17

   Good vs. Bad Reasons for a Slipped Deal

   1. BFBen Fiechtner16:49

   2. HSHarry Stebbings16:49

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

   3. BFBen Fiechtner16:54

      There are always unnatural things that happen. I think a good reason for me is, we try to pull it forward from the next quarter. We couldn't get through all of the required steps, and so it actually should've 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.

   4. HSHarry Stebbings17:20

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

   5. BFBen Fiechtner17:24

      Number two, you're gonna look at ... You know, most companies are gonna say, "Hey, leader, put in your pencil or your forecast number, and what you're gonna 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 calling a number, but two, you're also calling your shot on which deals are the furthest along.

   6. HSHarry Stebbings17:48

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

   7. BFBen Fiechtner17:51

      Yeah. No, you push for more.

   8. HSHarry Stebbings17:53

      I mean it-

   9. BFBen Fiechtner17:53

      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, wanna reverse waterfall where the deal back walkup is higher than the commit, right? And the total pipe gen, the most likely, all those fun things are better than the most likely, and then the total pipeline is, you know, killing it for the best case. Of course, you wanna reverse waterfall, but I think in week one, I'm pretty realistic about it, 'cause a lot of times they don't have the commit deals to actually back into the pencil in a lot of the organizations I've been.

   10. HSHarry Stebbings18:22

       But, like, are leaders wrong to push for more? When, when you, Ben, say, "Hey, 1.2," am I wrong to say, "Come on, Ben, we can do 1.4"?

   11. BFBen Fiechtner18:30

       I think the best leaders don't tell them stories, or believe the stories that they tell, 'cause great salespeople are storytellers of, "This is..." Every QBR... I'll put it this way. Every QBR I've ever been to, every AE puts up a slide that says, "Here's me finishing at 120% to plan." Every time. It's magical. Now, do 100% of AEs finish at 120% to plan? Never, right? So I think the, the, the best sales leaders I've been around and 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 a 13-week process to make sure that you're checking and understanding where the holes in your business are.

   12. HSHarry Stebbings19:06

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

   13. BFBen Fiechtner19:11

       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.

   14. HSHarry Stebbings19:29

       What does that involve?

   15. BFBen Fiechtner19:30

       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 has bad telemetry or bad adoption and usage and a big contract, I'm gonna prioritize those discussions."

   16. HSHarry Stebbings19:48

       Then we just put more CSMs on it? We give them more l- love? What do we do?

   17. BFBen Fiechtner19:53

       I think you're understanding the risk in week one for us. Yes, eventually you're likely swarming around it, but I think, s- 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 anew. Let's get a sprint call related to this, or a big deal review, or whatever you wanna call it to get the team on the horn, 'cause one of our top ten 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.

   18. HSHarry Stebbings20:23

       Yeah.

   19. BFBen Fiechtner20:23

       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 gonna tell you you're gonna land at this based on where the pipe gen, or 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 that, uh, it later just turns into more (laughs) of like, "How do you then look at conversion of pipeline?" And then in the last couple weeks, of course, it's, uh, just purely execution of are we doing the right things to make sure we're moving the needle in as short a timeframe as possible?

   20. HSHarry Stebbings21:02

       It is amazing to be as granular as this, 'cause so many founders will literally be pausing and taking notes on it. And so my question to you-

   21. BFBen Fiechtner21:08

       (laughs)

   22. HSHarry Stebbings21:08

       ... is, like, is it one... 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"?

   23. BFBen Fiechtner21:17

       For me, we chunk it into four chunks. So what we did is actually... And, uh, my SVP of rev op, Scott Peizer, he helped kinda document all this, and we realized it was to tighten up our own forecast cadence, and then we were like, "Holy cow, we're onto 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 p- 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, um, to make it easier to follow, but we think about it as, like, create, convert, close, and churn. Those are the four buckets. 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, do I have enough pipe coverage, all the things we 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, um, pipe by stage year to date? Or excuse me, same time last quarter, same time last quarter last year. Those types of things where you're dr- really trying to understand the health 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 Medpick 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, you know, key stakeholders or shareholders, whatever it may be. And then churn is the dreaded C where you're looking at throughout the time, "How do I look at..." In software, you can't... I can't do unnatural acts typically to get you to renew in less than, call it three to six months, so you're always looking Q plus one, plus two, and looking further out depending on the week and when you have more time to be really, really smart about seeing around corners.

   24. HSHarry Stebbings23:15

       So what was the... So we've got create, convert-

   25. BFBen Fiechtner23:18

       Close and churn.

   26. HSHarry Stebbings23:19

       What's core to doing convert well?

   27. BFBen Fiechtner23:22

       It's a great question. So one, you have all the stats to say where are deals stalled, and some of that can be, you know, CRM hygiene. Some of that can be... Hopefully that's what it is (laughs) and it's not lack of operational rigor. I think where we see a lot of this is, one, we use Medpick internally in 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 summaries Satur- 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 gonna 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 once you're aggregating those pieces-... in the convert part of the bulk of the quarter, in the heavy middle, you are absolutely focused on where are 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?

   28. HSHarry Stebbings24:22

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

   29. BFBen Fiechtner24:27

       Clari 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 and 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 cre- 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 Clari's saying, "Look, these are the five that are not gonna 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, um, 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.

9. 25:17 – 27:26

   Leveraging Teamwork to Close Deals

   1. BFBen Fiechtner25:17

   2. HSHarry Stebbings25:17

      How do you advise founders on leveraging the team to work more together to close a deal? What do you do in those cases?

   3. BFBen Fiechtner25:24

      I-

   4. HSHarry Stebbings25:24

      Is it ever like, ah, Ben, you went to a, you know, Wisconsin, this guy's a Wisconsin guy, like come in on this call, talk about Scani, and just build that rapport so it's a little bit more natural. Like, is that it?

   5. BFBen Fiechtner25:36

      I actually don't... So I think it's really hard to get a team to work together well on a- on a deal that isn't a good team to begin with. So I think about this more from, 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, it's been... 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 'cause they don't work as a fricking team (laughs) , right? And those that do can show up with three and say, "Yeah, we got each other's backs and we can interchange roles." Um, so I think I'd 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.

   6. HSHarry Stebbings26:39

      Convert, right? Um, convert. I have so many where I'm on the board of and they're like, "Yeah, you know, honestly, they just let it slip to next quarter. They love us, they love us, Ben, but it just slipped to next quarter." How do you respond when someone on your team says that?

   7. BFBen Fiechtner26:54

      I, hopefully at that point you've gone through, like, who's the decision maker, what is their decision criteria, right, what- what was the compelling event, is this budgeted and funded? The ch- 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 methodologies w- like exist. It's because if you do the homework, nine times out of 10 it does work, and I think a lot of it is just doing the right research and asking the right

10. 27:26 – 28:03

    The Biggest Reasons Why Deals Don’t Close

    1. BFBen Fiechtner27:26

       questions.

    2. HSHarry Stebbings27:26

       What are the biggest reasons deals don't close?

    3. BFBen Fiechtner27:29

       Like my gut, 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 for me. 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

11. 28:03 – 29:17

    Enhancing Sales & CS Collaboration to Reduce Churn

    1. BFBen Fiechtner28:03

       things done.

    2. HSHarry Stebbings28:03

       Talk to me about churn. When you look at this, the hardest thing is also the relationship between CS and sales.

    3. BFBen Fiechtner28:10

       Yeah. Yeah.

    4. HSHarry Stebbings28:10

       You know, you close the, we- we do the close, three, and then we think about four, churn. And often it's because I close Ben, and then I throw you over to, you know, whatever-

    5. BFBen Fiechtner28:21

       Yeah.

    6. HSHarry Stebbings28:21

       ... uh, 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 and adoption is great?

    7. BFBen Fiechtner28:29

       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 like what they're gonna 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 gonna solve all these issues, but we don't actually do a thorough sale." That's never gonna 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

12. 29:17 – 35:31

    Transitioning from Small Commercial to Large Enterprise Deals

    1. BFBen Fiechtner29:17

       for success.

    2. HSHarry Stebbings29:17

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

    3. BFBen Fiechtner29:28

       Yep.

    4. HSHarry Stebbings29:28

       I would love to discuss this kind of transition from, say, smaller commercial agreements to enterprise agreements, much larger deals.

    5. BFBen Fiechtner29:37

       Yeah.

    6. HSHarry Stebbings29:37

       What are your biggest lessons in terms of what it takes to grow from smaller commercial to large enterprise accounts?

    7. BFBen Fiechtner29:44

       So, and I think I was fortunate enough, like I started my career actually at Salesforce as a commercial AE, and then I got, was fortunate enough to move to the enterprise team and become a global account manager. Um, and a lot for me was, honestly, I looked at actually the move from commercial to enterprise, and it was funny. I sat down with my AVP at the time...They said, "Ben, you gotta treat this account like 80 little accounts." It's a big global conglomerate. They have multiple different P&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, 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-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.

    8. HSHarry Stebbings30:44

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

    9. BFBen Fiechtner31:02

       That's totally fair. I think, 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 'cause cost of sale and all those fun things. But 100%, like given the complexity of the internal stakeholders, the external stakeholders, you're going to need more people and more capacity and more yield, um, 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, right? I think a lot of times I've seen so many times, like, your favorite salesperson or the loudest squeaky wheel, right, or whatever, um, is going to ask for the most amount of resources. And sometimes you trust it, sometimes you don't. 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 gotta 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 gotta be willing to iterate and move folks around, like, without causing too much disruption.

    10. HSHarry Stebbings32:19

        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?"

    11. BFBen Fiechtner32:29

        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 stopped 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. Um, so when you do these enablement webinars and you're saying, "Hey, it's a mandatory two-hour session every Friday, we're gonna talk about product sales process," exactly, you fall asleep. If I am a good FLM, 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, 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 1,000 times a day, you probably go to breakfast, lunch, and dinner together, depending on your size of, of the company, of course. Like, 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.

    12. HSHarry Stebbings33:46

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

    13. BFBen Fiechtner33:52

        I think it's a big bet, right? And at Clariy 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 'cause they say, "Hey, there's more money there." Right? And that's always true, but I think you have to find your product niche and what, like, the unique problems your customers have and how your product solves it is where I would spend and put my chips. And I've found our friends that are saying, like, "We don't, we wanna be gen AI for very small startups. We don't wanna deal with the biggest companies in the world 'cause we can't build the capacity that they have." And I think that's a very intelligent decision.

    14. HSHarry Stebbings34:33

        So Stevie, the CR of Vanta, is also-

    15. BFBen Fiechtner34:35

        Yeah.

    16. HSHarry Stebbings34:35

        ... in 20,000. So I work with her closely, and she always says that actually you can stress test moving into enterprise, uh, 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?

    17. BFBen Fiechtner34:52

        Yes, I think you can. And sorry, what I meant is this, if you're shifting your capacity to enterprise, like, you better be very, very sure of it. But 1,000%, I think the more, even the biggest tech companies in the world, when they're calling on the other biggest tech companies in the world, like, you're gonna have different requirements, they are special snowflake, you're gonna have to invest R&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 gonna 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

13. 35:31 – 39:47

    Verticalization: Why, When & How

    1. BFBen Fiechtner35:31

       companies.

    2. HSHarry Stebbings35:31

       One thing I've noticed that really increases speed is much tighter product marketing and verticalization.

    3. BFBen Fiechtner35:37

       Yeah.

    4. HSHarry Stebbings35:38

       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?

    5. BFBen Fiechtner35:46

       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 gonna lose. So I think for us, right, like when we talk to med device companies, we show up and talk about forecasting in 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 B2B opportunities. You're actually forecasting in how many syringes or how many whatever they're gonna 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. 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 JPMCs, the Bank of Morgans, the biggest banks in the world, but sometimes you're not a good fit. So play where you fit well, um, and that's been a- I think a big thing I've learned through the last three stops.

    6. HSHarry Stebbings36:51

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

    7. BFBen Fiechtner36:56

       I think unless you have a verticalized product, it, it does cost money, right? And I remember a sales force exec head of sales telling me when 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. Um, so I think you have to be willing to take that if you're a certain size company, unless you have-

    8. HSHarry Stebbings37:25

       I don't understand why it's, why it's harder. Like product marketing is easier, word of mouth is quicker, um, product resonance is better, your understanding of the customer's better-

    9. BFBen Fiechtner37:34

       Yeah.

    10. HSHarry Stebbings37:35

        ... deal. Why is it slower?

    11. BFBen Fiechtner37:36

        So I, 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 ex- 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.

    12. HSHarry Stebbings38:25

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

    13. BFBen Fiechtner38:28

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

    14. HSHarry Stebbings38:32

        I would actually say a company that we just invested in actually. It's this German business called Allo, and it basically takes on Lightspeed and Toast for-

    15. BFBen Fiechtner38:39

        Okay.

    16. HSHarry Stebbings38:39

        ... 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, an Italian restaurant into Italian restaurants, a Taiwanese person into Taiwanese. Why?

    17. BFBen Fiechtner38:57

        Interesting.

    18. HSHarry Stebbings38:57

        Because people want to buy-

    19. BFBen Fiechtner38:58

        Yeah.

    20. HSHarry Stebbings38:58

        ... from people who are like them. And when you're in a neutral/foreign country-

    21. BFBen Fiechtner39:03

        Yeah.

    22. HSHarry Stebbings39:03

        ... 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.

    23. BFBen Fiechtner39:17

        That's fascinating business concept, by the way. Um, 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 most, um, or persevering the best, I should say, with the macroeconomic conditions.

    24. HSHarry Stebbings39:32

        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-

    25. BFBen Fiechtner39:39

        Yeah.

    26. HSHarry Stebbings39:39

        ... by doing that customer qualification, and actually you can dip your toe in the water too in a co- couple of core verticals. And so I think do it as early as possible.

14. 39:47 – 45:01

    Hiring Process

    1. HSHarry Stebbings39:47

       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?

    2. BFBen Fiechtner40:04

       How I think about salespeople and cheesy, 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. Like in any sales organization, you're gonna have problems and you look at them as opportunities.

    3. HSHarry Stebbings40:26

       How do you test for attitude?

    4. BFBen Fiechtner40:28

       I think two things. Uh, my favorite interview question, um, is somewhat testing for growth mindset. So, 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 it's, "I didn't have the great 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," I then know you probably have a growth mindset that you're self-aware enough to know that you're not perfect. We will edit out the fact that you said, "I just raised a gazillion dollars," so-

    5. HSHarry Stebbings41:07

       Yeah, yeah, yeah. Uh, bu- bu- but like, okay, 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 da da da?

    6. BFBen Fiechtner41:18

       Surprisingly enough, it's probably 60 to 70% of the time salespeople will say something that was outside of their control.

    7. HSHarry Stebbings41:27

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

    8. BFBen Fiechtner41:29

       Yeah.

    9. HSHarry Stebbings41:29

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

    10. BFBen Fiechtner41:33

        You can tell on folks like, yes, you're boasting about yourself a little bit on an interview, but I think some of it is the other piece on that attitude is how curious are they about the, the company, right? And how do they show up and how d- like, and nine times outta 10 with our company, I'm brutally honest and not a sales pitch, but I'm saying, "Hey, here's all of our warts." And you'll tell really quickly if 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.

    11. HSHarry Stebbings42:02

        It's similar for me when investing. I, to test attitude, I always wanna see an entrepreneurial mindset super early 'cause it's the biggest correlation-

    12. BFBen Fiechtner42:08

        Yeah.

    13. HSHarry Stebbings42:08

        ... 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, and no joke aside, and ac- it happened-

    14. BFBen Fiechtner42:18

        Yeah.

    15. HSHarry Stebbings42:18

        ... and I learned this. And, and the other is, "Oh, I came out of Cambridge and then I went to McKinsey."

    16. BFBen Fiechtner42:23

        Yeah.

    17. HSHarry Stebbings42:25

        Big difference in terms-

    18. BFBen Fiechtner42:26

        Yeah.

    19. HSHarry Stebbings42:26

        ... of the aptitude early. Okay.

    20. BFBen Fiechtner42:27

        Yeah.

    21. HSHarry Stebbings42:28

        So we have that in terms of attitude. Aptitude, what are we looking for here?

    22. BFBen Fiechtner42:31

        Yeah, aptitude, I think is, are you intellectually curious? So this you can figure out really quickly in an interview too. One, what are your questions? Like 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.

    23. HSHarry Stebbings42:49

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

    24. BFBen Fiechtner42:54

        (laughs) 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 gonna answer that. I think the thing is, is like you should ask genuinely what you're concerned about and what you authentically care about. So for me, if someone is... Like 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 Clari?" Like, shut up, no one cares at that point, right? (laughs) Like, let's be honest, they- if you say... Hey, my favorite interview question I ask all the time, like, "Harry, what's the one thing you'd change about your company?" Nine times outta 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 curiousi- 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. 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. You know what I mean?

    25. HSHarry Stebbings43:52

        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 that intellectually honest. I don't really give a shit about forecasting. I, I will close dollars and I'm a machine at closing and I love the sales game." Ah, you can sell, sell, I can sell anything.

    26. BFBen Fiechtner44:08

        If they check all the other boxes, I am, have no problem if money is your number one motivation. And I think most sellers try to hide it. Um, and there's, 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 gonna potentially fit in the culture, and B, how I can help you stay motivated.

    27. HSHarry Stebbings44:29

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

    28. BFBen Fiechtner44:33

        Heard that about you all. (laughs) Um...

    29. HSHarry Stebbings44:35

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

    30. BFBen Fiechtner44:38

        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 catchall 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. Um, so that's a question I think I ask a lot of clients at the, almost the end of every client conversation. Um, and I sing- the same thing

15. 45:01 – 46:24

    The Subtle Skill That Boosted Ben’s Success

    1. BFBen Fiechtner45:01

       for interviews too.

    2. HSHarry Stebbings45:01

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

    3. BFBen Fiechtner45:09

       I think one earlier on in my career was the fear of failure, for sure. Like I was very much motivated to say, "I, I can't lose at anything and I'm gonna do, I'm gonna outwork, outhustle, do everything within my power to make sure I don't lose." And that was one, I was talking to someone, actually our CEO the other day about this, of like on a bike, if you try to pass me on a bike when I was 30, 10 years ago, I would throw up trying to pass you. Like I would just, 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. I think for me, another one, and there's a motivation there that's like a competitive drive. And then the second piece I think is like, I don't wanna let people down. And I think one, that's hopefully made me be a great or decent people leader I should say. Um, but also like the impact you're gonna hopefully have with clients if you think that lens of like, I wanna make sure they walk away from this in a healthy spot, um, is another thing that I'm somewhat embarrassed a bit 'cause I don't wanna be like a people pleaser. I don't wanna 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 wanna let people down and I want them leaving with a great taste in their mouth regardless of any conversation, interaction, purchase, whatever

16. 46:24 – 51:56

    Authenticity vs. Tough Decisions: Strength & Weakness

    1. BFBen Fiechtner46:24

       it may be.

    2. HSHarry Stebbings46:25

       Listen, I can do, um, feedback review. I think from all the conversations I had before, your biggest strength is your bigness- 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.

    3. BFBen Fiechtner46:47

       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, um, 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 than if I try to sugarcoat it and be nice and not be intimidated to let you down. Um, and that's a huge thing that I've worked on, I'd say over the last three to four years.

    4. HSHarry Stebbings47:14

       Do we do take-homes in the interview process?

    5. BFBen Fiechtner47:17

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

    6. HSHarry Stebbings48:15

       Okay, good. So we have that. And then what are the biggest, or what are, what's the most common reason that reps fuck up in the interview process?

    7. BFBen Fiechtner48:23

       I think they're just unprepared. And if you're unprepared for an interview, like how are you gonna be for a customer call?

    8. HSHarry Stebbings48:28

       The only thing I'd probably say is maybe they're interviewing with 10 different people and so...... they may not. If they're in the role, then it may be different. But I totally agree with you.

    9. BFBen Fiechtner48:38

       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. Like, even if I didn't want that job, I better show up really, really well so that when they think about me (laughs) 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, that isn't so much to ask.

    10. HSHarry Stebbings49:06

        Okay, so going back, we have attitude, we have aptitude. Anything else?

    11. BFBen Fiechtner49:10

        Authenticity, which I think we've talked a little bit about. But authenticity of- I, 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 min- money-driven salespeople, there's salespeople you've met that are complete assholes but they own it, and then there's like- as long as you're authentically yourself, people are gonna 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.

    12. HSHarry Stebbings49:43

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

    13. BFBen Fiechtner49:52

        I think where we've looked at this and- an example from Clari, like, we had hunter farmer sellers. So I think the best- and, 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- 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 gonna have inputs from finance on marg- like, 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. 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, alignment, motion, talent, and what you're trying to drive, and use those design principles to design the comp plan.

    14. HSHarry Stebbings50:43

        You said before there about the hunter farmer. I'm just intrigued. I have Dave Kellogg, uh, who I love-

    15. BFBen Fiechtner50:49

        Yeah.

    16. HSHarry Stebbings50:49

        ... who was a guest on here before. And he's like, "You never wanna have your farmer against someone else's hunter."

    17. BFBen Fiechtner50:56

        Yeah.

    18. HSHarry Stebbings50:57

        How do you prevent that?

    19. BFBen Fiechtner50:58

        By the way, I love him too, and his- I forget, he had a blog recently about like, six bullets. I shared it with my- of like, the greatest career advice. I'm like, "Holy shit, is he good." Um, shared it with all my leadership team.

    20. HSHarry Stebbings51:09

        He's amazing, honestly.

    21. BFBen Fiechtner51:10

        Yeah. He's way better at podcasting than I am, is what I can tell you at 50 minutes in. 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. So, I think a lot about how do you- back to your earlier question about where do you put capacity, where it's gonna drive the biggest yield. For us, that was a move to enterprise, and we got very, very specific of our enterprise AEs had a hundred accounts in their territory. We're like, "That's never gonna 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 solve that you have for that client base, you're gonna put people in the right space, and then you're not gonna run into that. But it's gonna happen probably in longer tail businesses all the time.

17. 51:56 – 58:30

    Quick-Fire Round

    1. BFBen Fiechtner51:56

    2. HSHarry Stebbings51:56

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

    3. BFBen Fiechtner52:01

       This is the lightning round? Love it.

    4. HSHarry Stebbings52:03

       This, this is an absolute lightning round. What sales tactic has died a death?

    5. BFBen Fiechtner52:08

       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.

    6. HSHarry Stebbings52:19

       What about big corporate events? Like- or not big corporate events, sorry, but like, "Hey, we take our big customers to a box at Taylor Swift. We do big golf days." Is that still a thing?

    7. BFBen Fiechtner52:30

       Not always for my beer budget and champagne taste, but I, I mean, Salesforce still sponsors Formula 1, and by all the looks of it, there's- lots of people were near you last weekend having a great time.

    8. HSHarry Stebbings52:44

       What's the biggest lesson from UiPath?

    9. BFBen Fiechtner52:46

       Be extremely intelligent and design your sales team based on product market fit. When I joined UiPath, we were designed in geographies, and I think we- I had the dis- or I had the pleasure of running their key accounts program, which called their top 100 accounts. I had banking and healthcare clients, so the JPMCs, the HCAs, the Cignas 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 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." 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. And I think 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 have been an anomaly, that might have been an exception." And in that case, it was, "Holy shit, this is really working and we gotta push all our chips in," and the company rallied around it and did it.

    10. HSHarry Stebbings54:04

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

    11. BFBen Fiechtner54:07

        I think too often they come in with desi- design playbooks, or, "This worked at this company," and blah, blah, blah, "And I'm gonna 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 gonna 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 journal- journey, I- I guess I should say. 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.

    12. HSHarry Stebbings54:51

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

    13. BFBen Fiechtner54:56

        There was an exec at Salesforce that I think I thought I had to be something I wasn't, 'cause 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- 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 try to be something you're not.

    14. HSHarry Stebbings55:37

        Ben, what question did I not ask you-

    15. BFBen Fiechtner55:39

        (laughs)

    16. HSHarry Stebbings55:39

        ... that I should have asked?

    17. BFBen Fiechtner55:41

        (inhales deeply) Uh, well played, Harry. Well played. Um...

    18. HSHarry Stebbings55:46

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

    19. BFBen Fiechtner55:49

        You've done 3,000 podcasts?

    20. HSHarry Stebbings55:51

        Yeah.

    21. BFBen Fiechtner55:51

        Holy cow. Um...

    22. HSHarry Stebbings55:54

        Yeah. I'm not that young anymore. (laughs)

    23. BFBen Fiechtner55:56

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

    24. HSHarry Stebbings56:00

        Thanks, dude. That's funny.

    25. BFBen Fiechtner56:00

        You could- Zoom filters work well.

    26. HSHarry Stebbings56:02

        What is the secret to a happy marriage?

    27. BFBen Fiechtner56:04

        Aptitude, attitude and authenticity. (laughs)

    28. HSHarry Stebbings56:08

        Same?

    29. BFBen Fiechtner56:09

        No, I- I think the biggest thing I would say on marriage is, um, yeah, be authentically you and share exactly what your feelings are like. 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.

    30. HSHarry Stebbings56:26

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

Episode duration: 58:30