20 Sales: The Stripe Sales Playbook; Who Should Create It, When Should it Be Done, Where Do Many Go Wrong | How To Identify 10x Sales Hires and How To Structure the Hiring Process in Sales with Jeanne DeWitt Grosser, Head of Americas Revenue & Growth @ St

Jeanne DeWitt Grosser is Head of Americas Revenue & Growth @ Stripe. In this role, Jeanne is responsible for all sales functions across the region including Sales Development, AEs, Solutions Architects, and many more. Jeanne also continues to spearhead Stripe's Enterprise strategy. Prior to this role, Jeanne was Stripe's Head of North America Sales where she built out Stripe's Acquisition Sales teams. Pre-Stripe, Jeanne was CRO @ Dialpad and also spent many years at Google in numerous different roles including most recently as Director of GSuite SMB & Mid-Market Sales, North America and LATAM. In Today’s Episode with Jeanne DeWitt Grosser You Will Learn: 1.) Entry into Sales: How did Jeanne make her way into her first sales job in tech? What did Jeanne learn from her many years at Google about how sales should interact with engineering? In hindsight, what would Jeanne have done differently/improved from her time with Dialpad? How did the role with Stripe come about? 2.) The Playbook: Does the founder need to be the one to create the sales playbook? When is the right time to bring in the first sales hire? Should they be a sales leader or rep? How does both the playbook and the type of sales hire change when hiring for a product-led-growth motion vs a traditional enterprise motion? What are the single biggest mistakes founders make when hiring their first in sales? 3.) The Hiring Process: How should founders structure the hiring process for their first sales hires? What did Dialpad do in the sales hiring process that worked well? How has Jeanne taken that to her hiring process at Stripe? What should be achieved or learned in each consecutive interview? How can founders use sales case studies most effectively? How can founders know if sales candidates truly have a strong grasp of the product? What are early signs of a 10x sales hire? What are red flags to look out for in the process? 4.) Sales Onboarding: What does the ideal onboarding process look like for new sales hires? What tasks and duties should all sales hires perform in the first 60 days? What are early signs that a new hire is not performing to the right standard? How does the first few months differ for sales reps when comparing a product-led-growth company to an enterprise company? What should sales leaders do to ensure that new hires engage with product and customer success efficiently?

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

• 0:00Harry Stebbings?

  Welcome to 20 Sales with me, Harry Stebbings. This is the monthly show where we interview the top 10 sales leaders in the world to share their tips, tactics and strategies when it comes to scaling sales teams successfully today. And who better to join us today than the one and only Gene Grocer? Now, Gene is the Head of Americas Revenue and Growth at Stripe. In this role, Gene is responsible for all sales functions across the region, including sales development, AEs, solution architects and many more. Gene also continues to spearhead Stripe's enterprise strategy. And prior to this role, Gene was Stripe's Head of North America Sales, where she built out Stripe's acquisition sales team. Pre-Stripe, Gene was CRO at DialPad and also spent many years at Google in numerous different roles, including most recently as Director of G Suite SMB

• 0:41Harry Stebbings?

  and Mid Market Sales for North America and Latam. I'd also want to say a huge thank you to Claire Hughes-Johnson for some fantastic question suggestions, and then also the one and only Danny Hersberg at Sequoia for the fantastic introduction in the first place. It would not have happened without you, Danny. But before we dive into the show today, Sales Loft is the leading sales engagement platform, helping sales teams drive more revenue with the modern revenue workspace. It's the one place sales teams can go to prospect, manage active deals and get the insights they need to coach seller performance, forecast with accuracy and find out what steps to take to close more deals. Some of the world's leading companies like IBM, Shopify and Stripe all love a new Sales Loft and so can you. It's the new way to sell and find out more today at salesloft.com. And founders, if you've

• 1:24Harry Stebbings?

  got recurring revenue like so many of you have, there is a smarter way to grow your business. As a VC, this pains me to say, Pipe is a completely new way to finance growth without taking on restrictive loans or diluting your ownership. If you have proven product market fit, your recurring revenue streams could be your biggest asset. Pipe is the world's first trading platform that turns your recurring revenue into upfront growth capital within as little as 24 hours of being connected. It's fast, flexible and founder-friendly and they also work across many industries from SaaS to direct consumer subscription, media and entertainment and many more. And with Pipe, there are no loans, no dilution, no warrant coverage or restrictive covenants. Pipe is growth on your terms and right now, 20 Sales listeners get trading fees waived for 12 months, which could save you tens of thousands of dollars depending

• 2:10Harry Stebbings?

  On the size of your business, sign up today at pipe.com/20sales to start trading today. And finally, to scale your business, you need customers. But this CRM software model is 35 years old and it's never evolved to properly support modern businesses. Most legacy platforms were built for a single rigid, repeatable sales process. But guess what? Copper is a dramatically different kind of CRM. Built for Google Workspace businesses, Copper works right alongside you in your inbox. And it's so flexible and versatile that you'll love it regardless of how you run your business. Plus, it requires virtually no training because it works just like all your other Google apps. Get set up in less than a day and easily customize your CRM to fit your needs. I promise you, this will be the first time that your team love you as a leader for choosing a CRM solution.

• 2:54Harry Stebbings?

  That is a personal experience of mine. And so see why more than 30,000 businesses love Copper, a flexible CRM that grows with you. Get a 20% discount on any annual plan. Just go to copper.com/20vc. But that's enough from me. So now I'm so excited to hand over to the one and only Jean Grossette at Stripe.

• 3:17Speaker 01

  You have now arrived at your destination.

• 3:20Harry Stebbings?

  Jean, this is such a joy for me to do. I heard so many great things from Danny before the show. I've been excited for this one for a while, but thank you so much for joining me today.

• 3:28Speaker 02

  Thank you for having me. Excited to be here too.

• 3:30Harry Stebbings?

  Not at all, but I want to start with a little bit of an entry point. So how did you first make your way into the world of tech? And then how did you come to run some of the most powerful sales orgs today?

• 3:39Speaker 02

  So I started off looking up to my father. He worked in tech, so he spent 17 years at IBM, was one of the first people to sell a PC. He just had this really dynamic career. I think it's funny, like what I remember most about it was he would go on all these business trips. And when he would come back after a week away, he'd bring me a little toy, which is very memorable as like a six year old. But it just made me want to have this international career when I grew up. And when I was looking closer to graduating from college, he and I had a conversation on the wine train in Napa, trying to figure out what I was going to do. I wanted to come back to the area. I wanted to have a dynamic career. And he really got me to think about tech.

• 4:18Harry Stebbings?

  Because how did you land at Stripe?

• 4:20Speaker 02

  I started at Stripe because Claire Johnson, our C O O, was my first boss at Google back when I was, you know, directly out of college. So when she joined Stripe, I frankly, I wasn't familiar with Stripe at all. She called me and said, you know, we're building a go to market org here. Would love to have you join. I was at another startup at that point and said, you know, hey, I'm situated, but I'll keep my eye on this. Couple of quarters after that, I gave her a call and was like, I think I might want to come and chat with you. And was in her office within, I think about forty eight hours. And six weeks later had a Stripe offer in hand.

• 4:53Harry Stebbings?

  I love it. Yeah. I do want to start on that kind of bringing on the go to market and the sales team though. Cause I think a lot of founders struggle in terms of the right time. I always have the thought that bluntly, the founder should build out the sales playbook. Do you agree with that notion? Or do you feel that it can be brought in with bringing in a sales team?

• 5:09Speaker 02

  So I think it depends on exactly what you mean by that. So I think a founder needs to be really core to determining initial product market fit. And you're going to get that by talking to lots and lots of customers. And so I don't think you want founders not doing that. Because I've always sort of said, sales is one part revenue and one part R and D. And so you really want that founder connectivity at the beginning to find that R and D piece. But I do think that founders underappreciate the fact that sales is a skill, just like writing code is a skill. And so they often, I think, maybe hang on to that role as the initial salesperson, maybe a little bit too long before thinking about, perhaps I want to bring in somebody who has good sales skills in this area.

• 5:54Harry Stebbings?

  The incredibly unfair question, I agree, sometimes founders do wait too long. What are the signals that suggest now is the right time to bring in a sales team or a head of sales?

• 6:04Speaker 03

  Yeah, I think bringing in a sales team often probably should have happened earlier than founders anticipate. And so if you're past the point where a founder can reasonably have these conversations, that's kind of the moment. I do a lot of mentoring of founders and I often find that's one of the things they'll say is like, you know, I'm now having to take customer calls for like three, four, five hours a day. I need to work on product roadmap, you know, what should I do? And immediately think to myself, well, probably you should hire. A salesperson. So I think you don't have to, you know, get your head of sales in at that moment. You know, you want to get probably a seller who's done it before, who has some amount, you know, enough experience that they can sort of be self-driven on this front. But I think it's hard sometimes to hire your head of sales at that point because you may not ultimately know

• 6:50Speaker 03

  who you're going to wind up selling to as you get to more and more scale. And different sales leaders spike in different areas. And so a mistake that folks can make would be hiring the wrong profile of a sales leader, you know, because you don't yet know what you really need.

• 7:04Harry Stebbings?

  And so do you hire one? Do you hire two? Do you hire three? How do you think about if we're not hiring that head of sales, we're bringing in reps? How do we make sure that we're not bringing? Because I think often something I see also is they bring in one and they're just bad reps.

• 7:16Speaker 03

  Right.

• 7:17Harry Stebbings?

  And then they think of the problem with their model and it's just the rep. Should they bring in two or three? How should we think about that?

• 7:22Speaker 03

  Yeah, I agree. I think you want to have, you know, a handful. So again, you don't get the rep problem. You're also at that point, I think, trying to get to some level of pattern recognition, both on are you honing in on an ideal customer profile? Are you seeing replicability anywhere? You know, it's hard to trust a single individual's point of view on what the pattern is. And so I do think you're going to want two to three folks to sort of corroborate that pattern as being, you know, true versus sort of a single individual's point of view. But two to three people versus going out and hiring 10, 20, you know, is obviously very different. And at that point, typically you'll have some other functions that are more operational at the company that you can kind of collapse everybody under until you get your formal head of sales.

• 8:04Harry Stebbings?

  So Jean, you are luckily appointed to be my advisor for this hypothetical startup that I'm running. You've advised me now, we need like maybe two to three reps, not a head of sales. And I agree, now's the time. I'm spending way too much time on customer calls. Help me. I need to do the process and look for someone. What non-obvious characteristics do amazing sales reps have from your experience that I should be looking for now?

• 8:28Speaker 03

  Absolutely. So you, again, you're in early product market fit stage. There are some things that you need. One, you've got to have a product oriented salesperson. So somebody who's going to get deepen your product, geek out on it, can articulate the vision and the, you know, product capabilities in line with how a founder would, which is very different than hiring somebody who maybe has, you know, worked at Salesforce for the last 10 years, right? So you've got to find that person who I think is a little bit nerdier, a little bit more product oriented than maybe when you're at scale. Second, you've got to test for that pattern recognition piece. So is this somebody who's going to give you good feedback about what is actually working versus be all over the place and sort of jump on whatever

• 9:11Speaker 03

  happens to come in front of them because you're trying to figure out where you have replicability, where your product is working and where you could scale from a go-to-market perspective. And then I think the last is you've got to find somebody who's going to be culturally aligned. You know, tech founders have like a real apprehension about sales. There seems to be this point of view that we're all coin operated, we're all effectively like car salespeople, right? And that's just really not actually true. You know, you obviously have tried to set a culture and I promise there are salespeople out there who can mirror your culture, but making sure that you have that too, so you don't have the body rejecting the organ.

• 9:45Harry Stebbings?

  If we go back to the actual process, we mentioned there are some of the core characteristics we're looking for. How do I actually structure a hiring process? I've never hired, not a head of sales, but a sales rep before, like it's, do I hire them in one meeting, two meetings, three, like how would you advise me to structure the actual hiring process?

• 10:02Speaker 03

  Yeah, well, first of all, let's hit on the word you're using, which is structure. So I think that's one of the mistakes that folks make is it should be a structured hiring process. You want to sit down and figure out what you think is going to need to be true about that individual and then design multiple interviews that test for those capabilities. When I was at DialPad, one of the things we actually did was we brought folks in to the office. It's hard to do it in COVID, but like into the office for like a half day. And we actually just like let them, you know, sit beside our salespeople, stuck them on chat, saw, you know, if you dumped them in the deep end, could they actually sort of figure out how to respond to some of these things? And kind of gave them a hands-on experience with it because we figured out that that was like a good way

• 10:45Speaker 03

  to separate who was like really a startup salesperson from somebody who was a Sales person who wanted to work at a startup. But you know, that's one of the things we've also done at Stripe, right? Is you have a homework assignment, something that's very reflective of what you're going to ask that person to do on day one when they show up. And it's a good way to test whether or not they're going to be capable of executing that thing. Particularly because at the beginning, you're not going to get much more than a phone and a computer. So if they can do that before they even shown up, probably higher likelihood that they're going to succeed.

• 11:15Harry Stebbings?

  So just so I understand this, so I do a homework assignment before the first meeting or in it with you?

• 11:20Speaker 03

  In it. So look, you've got to sell your startup first. So you gotta, you know, it's equal parts, the first one or two calls are going to be equal parts. You're interviewing them, but they're also interviewing you. Moving to a startup is a risk. So once you've gotten to the point where there's mutual interest on both sides is then when you get into the more core part of the interview. And through that, a lot of it's behavioral and you know, they'll just answer questions through the interview process. But then part of it is we do give people, you know, two to three questions to prepare in advance. Oftentimes with like, hey, you get three slides. And you don't want to give people a homework assignment that's going to take them 24 hours to complete. They've got a day job, you know, but enough where you're putting a little sweat equity into proving that you really want this.

• 12:03Harry Stebbings?

  No, I totally get you. Okay. So that's one, we have that homework assignment. We come, I've blown you away. What next? I've impressed you with the first homework assignment slash case study. What happens in meeting number two? Do we have a friendly get to know you and talk about my ambitions? Like, how do we literally structure the next step?

• 12:20Speaker 03

  Got it. Yeah. So before that homework assignment part, what we do are a set of screens. A lot of those are, you know, talking through your background. You kind of see what folks highlight, asking a core set of questions that get at someone's sales skills. And then you flip into this phase. So normally with this homework assignment for us, there's typically around four total interviews. So one is going to review this project and then the other three are testing for alignment with our operating principles and then sales skills. So from a sales skill perspective, you know, you would talk through the most complicated deal that they've worked on. Or have them pitch you on their product and have a mock sales call around that or talk through. How you do pipeline management, talk through objection handling, your worst loss,

• 13:05Speaker 03

  you know, how you've gotten into an account that was totally cold, right? So those are a bunch of different things you might ask about. And then questions that are probably getting reused across the company that again are getting at values in how you solve problems and how you do the job. And those are typically behavioral, where you'll talk about things that they've done in the past that and see if the way they went about solving that thing is how you would want that done at your company.

• 13:28Harry Stebbings?

  I always find like attribution an interesting one where people can often acquire achievements that maybe aren't their own. How do you detect for bullshit in the, oh, I increased revenue by X and oh, I did this and this when actually it wasn't there? What are the signals of bullshit detection?

• 13:43Speaker 03

  Yeah, that is a good one. So normally, you know, you'll walk into an interview, maybe I have eight questions I'm planning to ask, but sometimes I'll only ask two because after you get the first one, it's leaning you down another path where you want to just dig in further. And so typically you get at that by increasingly following up, asking why, asking how, and seeing if they can click down into the details or if they stay at 30,000 feet, very buzzwordy, et cetera. I think that's the other like key thing from a startup interview perspective is you can get really enamored when people say sort of the right vocab. You know, you interview a marketer and they talk about like account-based marketing and you're like, yes, more of this, right? But then how did you execute account-based marketing?

• 14:26Speaker 03

  You know, ditto on sales, people will talk about, oh, you know, we just do this really tight sales process with seven steps. Well, great, what are those seven steps? Can you rattle them off? What are the exit criteria of each of those steps? And really figure out if they're walking the talk.

• 14:39Harry Stebbings?

  Say we've done that and now you've hired me. Yes, I'm joining Strippers, you know, a new rep. Fantastic, exciting. The hardest thing of all, I think, that most startups mess up, onboarding process. What does the best onboarding process for new reps look like? And how do you like to structure it?

• 14:55Speaker 03

  Yeah, this is something I was really impressed with at Stripe when I started. So for a company of the scale we were at at that point, it was a full week of just spin up. And you had sessions with John and Patrick where they were really, you know, spending time outlining the culture, outlining the company vision, which I felt like drove a lot of alignment out of the gates. And then, you know, day two, I think we would all get thrown into the support queues. And so that was really great at teaching our users first orientation and getting hands-on experience with customers and learning the product. So, you know, you would get a bunch of the questions that were coming inbound and a bunch of materials and you'd have to just go and, you know, find the answer in them, which that's how it's going to be at a startup. You're not going to have a perfect playbook. And so you get the playbook that you have as it exists.

• 15:40Speaker 03

  And then you start to figure out, you know, how do you go answer things beyond that? But that is one of the things that when I came into Stripe, we didn't have from a sales perspective. You know, you basically still were in this super smart, kind of reactive like Q and A for sales, and there wasn't a process. And so what I did for my first 30 days, I just went out, figured out, you know, where there were patterns and then started to put in what I thought was going to be our sales process and based on hands-on experience. And then that was what we trained people on. So here are the questions you need to ask. Here's what the agenda of your first call should look like. Let's start getting some replicable content that people can present and just build that from there.

• 16:17Harry Stebbings?

  So for me now joining Stripe, in terms of like the onboarding process, like what does my first week look like? What does my first month look like? When do I speak to my first customers?

• 16:26Speaker 03

  Your first week at Stripe right now is very pan-Stripe, though actually, salespeople are with product people, with engineers, folks in recruiting, et cetera. And it's still similar to what I just described, where John and Patrick talk and you basically get a broad lay of the land of the company strategy, all of our products, operating principles. And then the second week is when you flip over into sales. And this is where we go really deep on here are our customers, here's how we segment, here's our ideal customer profile. Let's actually start talking about the value proposition, our core messaging, objection handling. So you sort of get crash course on the Stripe sales process because I believe strongly you want to get folks in front of customers. Right away. A savvy salesperson can talk to somebody actually knowing very little about the product they're selling.

• 17:11Speaker 03

  Because what great salespeople do is ask good questions. And so if you can teach folks what questions to ask out of the gates, they actually can run calls pretty effectively. And then just admit when they don't know the answer and go back and get it. So we're trying to get people in the deep end on calls right out of the gates. This is hard if you're super, super early from a sales perspective, but pair folks up, obviously with more tenured reps. Do a lot of shadowing, or if you have solution architects, if you're selling a very technical product. If you take a tenured SA and a new salesperson, they actually can be really powerful together. But tons and tons of shadowing and call feedback is sort of the rest of the first 30 days. And then, you know, we really start getting into what's it going to take to hit your number?

• 17:52Speaker 03

  Are you talking to enough people? You know, are you actually developing opportunities, starting to progress them further in the sales process? One of the things I think Stripe does a really nice job of is having spin up buddies. So for the first 90 days, you get a tenured Stripe salesperson, whose job it is to help make you successful. And the two of you really pair up to get you off the ground.

• 18:11Harry Stebbings?

  There are a couple of things I have to unpack. You said kind of hit your number. Jean, I'm a startup founder for the first time. I don't know how to set quota. How do I set quota? Do I go really easy so they feel great and feel confident? Do I push it really hard so they're really ambitious? How should I set quota?

• 18:27Speaker 03

  Yeah, so the way we did this at Stripe, which I think worked well, was you want to build a sales org that if it does what it's supposed to do, you would obviously invest your next dollar in it. So we sat down with go to market with finance and designed our quotas to do exactly that. And then we had a ramp curve into them. So it gives folks breathing room to come up to speed, to learn, but progress towards ultimately what productivity is going to need to look like. And then what we did at Stripe was also, we started with team based quotas. You know, you're learning. We also started with lower leverage. So again, you're not, don't have as much at risk. And as we got better about understanding what was achievable, you know, where was something replicable?

• 19:09Speaker 03

  Then we started increasing leverage, moving things more towards individual, you know, et cetera.

• 19:15Harry Stebbings?

  On 90 day check in, you're my boss, Jean. What do you expect me to have achieved in those first 90 days? What's the, oh, Harry's doing well. We're happy with how Harry's progressing. What are the signs?

• 19:25Speaker 03

  Number one, first and foremost is, are you mastering the product? And how to talk about it to a customer. So very enablement and learning oriented in the first 90 days. And so, and you get good feedback on this. If you're doing a lot of ride alongs, then you know, their spin up buddy is can be pretty discerning of, is this person rapidly rocking the product? Or am I constantly having to remind them of here's how this actually works? Or they're missing things. So a huge part is just, are you actually learning and incorporating what you need to know? But then beyond that, you know, sales ultimately is a math game. And so if you have that target, you can reverse engineer that, right? Of in order to hit this number, you need to close this many deals of this size. It take, you know, you win at this rate. It takes this amount of time.

• 20:10Speaker 03

  And so you actually can be able to tell your salesperson by 90 days in, you know, I need you to have created N opportunities, you know, of this average size. And then we can ask ourselves whether or not you're there. If you are, awesome. How do we accelerate that much more quickly? And if you're not, then well, where within that funnel do you seem to be off? Are your deals too little? Do you not have enough? If you don't have enough, are you talking to enough people? Are you talking to the right people? Right. And you can start to run a diagnostic.

• 20:37Harry Stebbings?

  On the flip side of that, then, if we have that as the, this is what looks good. What are red flags where you're like, I think we might've made a mistake with Harry. What are the signals that suggest someone isn't meeting the bar?

• 20:48Speaker 03

  One would be what I just mentioned is like, they're not really learning the product. And it's pretty easy to pick that one up, both in just listening on sales calls. And then also in talking to them in one on ones and just asking how they're thinking through, how they want to approach positioning our product within a specific opportunity. So I think that's, that's a huge one. And then the other is how they're approaching getting to their number, right? Can they tell you exactly what needs to be true? Or are they still sort of just showing up every day and doing what's in front of them, but not proactively driving towards the outcome? So a great rep typically would come to me in a one on one. And say, you know, Jean, my target is X. I'm going to need to close 20 deals to hit that.

• 21:30Speaker 03

  You know, here are, at this point, the ones that I think are likely to help me get to that number. Here are the ones that I'm working on developing, right? And they're actually very systematic. And again, understand the math behind the selling that they're doing. And also, I think are honest about where they might be need help or are stuck. I always get nervous about sales reps who think they've got it all sorted out and want to keep you at arm's length. Because the best ones typically know where they can leverage other people in the org and really want to do that.

• 21:58Harry Stebbings?

  Speaking of leveraging other people in the org, for me as the CEO, back to me as the CEO and you as my advisor, what can I do to encourage sales to interact more efficiently with both customer success and product? How can I create these synergies where they're maybe traditionally more siloed?

• 22:14Speaker 03

  Yeah, I think one of the things we've done well at Stripe is getting product engaged, you know, from a sales perspective and having product on the front lines. One, it's a great way for them to get feedback. Two, great way to have, you know, empathy. And often you can produce like these perfect documents, great quantified data, and then you bring someone on a sales call and they get that aha moment. But you also want to use product efficiently. So I think, you know, we're thoughtful around having some level of gating so that, you know, whether it's me or another leader is deciding when we're pulling product in. A lot of salespeople love having product on their call, right? Product should be pretty darn good at pitching as well. It has a stronger point of view often on the vision because it's in their head. But anyway, I typically am all for get product on calls.

• 22:57Speaker 03

  And then from a customer success perspective, you know, that's another key one where I think you want to have, really think about architecting the customer journey and in particular, handoffs between organizations and having a strong feedback loop around those handoffs. Because often, you know, sales can do things that just really aren't setting customer success up for success. And so you want that feedback because we can often change things that will make, you know, downstream lives easier. But then similarly, when you got things downstream, you really need customer success showing up so that the sales team can continue to focus on driving revenue.

• 23:31Harry Stebbings?

  What does sales do that doesn't set customer success up for success? What makes that difficult?

• 23:37Speaker 03

  Yeah, so this is like the key challenge, particularly as companies move more and more to consumption-based models. The sale is really not done when you sign a contract. Actually, at Stripe, we just call it deal signed because that's all it is. We got a piece of paper that has some ink on it, but like you haven't really won anything until a customer is live, processing volume, you know, and successful. So typically, it's that you haven't actually sussed out the customer's ability to deploy and ramp with your product. You gotta dig below the pitch deck. You know, you can convince a customer that your product's gonna be valuable, but then you also need to make sure that they really can execute it. So I think that's where sometimes sales and customer success can struggle and customer

• 24:20Speaker 03

  success can feel that, you know, sales is chucking something over the fence. And so we really pull those things forward into the technical validation stage to make sure somebody can actually deploy.

• 24:30Harry Stebbings?

  Is it difficult in a very product-led growth motion in terms of sales feeling important enough? When product-led growth and product is so central, then they're like, fuck, product makes up like seventy-five percent of revenue and we're twenty-five percent with our traditional enterprise sales, we're not that important. Is it difficult to make them feel important in such a PLG motion?

• 24:50Speaker 03

  Yeah, so it's definitely, it's different, right? Than a company that's like hardcore enterprise sales soup to nut. But I think what's important to remember is you put sales in place for a reason. And typically, in that segment of the market, you do need sales. So at Stripe, as an example, product-led growth, sort of like the online self-search channel, was awesome for, let's call it a Series A, Series B company. The minute you get past that, it doesn't work anymore. You're not like, if you build it, they will come. People are not coming to the website and just signing up. They really need to talk to a human and go through a validation. And you can see when sales team in place, our deal sizes got a lot bigger and we started winning a different class of company than we had won before sales.

• 25:35Speaker 03

  And so I think it's just important to remember, product-led growth can be awesome for a certain portion of the market. And if you can get to like very high revenue numbers on that portion, kudos to you because it's very efficient. But when it comes to pursuing larger accounts, multimillion dollar deals, pretty rare to do those without a human involved.

• 25:53Harry Stebbings?

  Totally agree. In terms of those bigger accounts, that bigger chase, do you do postmortems?

• 25:58Speaker 03

  Oh, yeah.

• 25:59Harry Stebbings?

  How do you structure them? How often do you do them? What do they look like? I'm fascinated.

• 26:02Speaker 03

  Yeah. So I mean, it's very typical sales practice to do loss reviews. At Stripe, we actually purposefully, so Stripe actually doesn't like to say postmortem. We like to say retrospective. It's more of a positive frame. So, but actually in sales, like, you know, purposefully adopted the language that the engineering organization was doing to again, sort of have that cultural alignment. But one of the things actually we do is like deal pre-mortems, and we actually call it that. Where before you've lost the thing, you know, you're mid-cycle, you actually go through a review to think through all the ways in which you could lose this so that you can proactively shore those up. And we'll do these deal pre-mortems where you bring the team together.

• 26:44Speaker 03

  And the goal is to have just a very intellectually honest conversation about your opportunity. And, you know, this, no one's trying to be critical, but purposefully sort of tear the deal down. So you can build it back up hopefully that much stronger. And then, yeah, we do do quarterly loss reviews. If you have a major loss, we'll do it right after we lose it. But then we'll do them, you know, more broadly and try to find again, patterns, themes, and what you would do differently.

• 27:09Harry Stebbings?

  Who's invited to the loss reviews? Is it just sales teams? Is it product? Is it customer success? How do you think about the right people to have in the room?

• 27:16Speaker 03

  Yeah, no, it ends up being all of them. So in the loss reviews, right now, actually, you know, we're now at a larger scale. And so we have one person team who helps us run this. But he'll prepare a bunch of content and then you often find when you've reviewed the losses and you can put in sales force, loss reasons, those types of things. You wind up with like clear go-to-market challenges where our messaging, our strategies off, as you think about positioning yourself relative to competition. We end up with like operational things where sort of roadblocks in your deal velocity actually wound up holding you back and killing the deal. And then you end up with product gaps. So we'll talk through all. Those and they influence product roadmap and then obviously go to market changes as well.

• 27:55Harry Stebbings?

  A final one that is a challenge, I think, again, for a lot of earlier stage founders. Relationship with heads of sales. What's the ideal relationship between the head of sales and the CEO? How often should we meet? What does that look like in an ideal fashion? Again, first time founder, I have no idea.

• 28:10Speaker 03

  Yeah, I think it's a key relationship, just like your head of product is. If you're not hitting revenue, it's either a product problem or a sales problem or, you know, some combination of the two. But you've got to be on the same page between the head of sales and the founder about A, what feedback they're getting from the field and what they think they can improve. So when I was at a dial pad, one of the things I think I could have done better was We on our revenue plan, as startups often do, was a stretchy revenue plan. And I think I came from a place at Google, you sort of had OKRs. And, you know, the goal was sort of get to seventy percent of your stretchy thing, right? And that's actually you delivered well. And so I was fine signing up for this stretchy target because in my mind, I was like, okay,

• 28:55Speaker 03

  I know that we all consider this a stretch. And so if we're somewhat off pace, that's sort of an expected outcome, right? But we want to sign up for the biggest thing possible and really push ourselves to get there. I don't know that the CEO and I were thoroughly tied out on that and understanding. So we built a full operating model of sort of like what needed to be true underneath that and how, you know, audacious some of those goals were. And that was something I missed, I think, in how he and I were communicating and understanding like where we thought, you know, this is just, we've got to execute this thing versus where like, we're really trying to do something that's like discontinuous from the trajectory of the business today. So I think that's one is like tie out on your operating plan and like, are you agreed on the achievability of targets?

• 29:36Speaker 03

  But then two, you really got to have, I think, that CEO, product, sales, all in one room, feedback loop of what are we hearing? What do we want to do about it? You know, how do we refine?

• 29:46Harry Stebbings?

  My question to you is, and it's a really hard one. Sales are not going well in my startup. They're not going well. We've missed numbers and the team feels it. What do I do then? Like, do I get everyone excited, get everyone jacked up again? But they've been failing, like it is not okay. How do you respond to a team that's not hitting numbers?

• 30:04Speaker 03

  Yeah, I think it's more empowering when you've got to be honest about it. At a startup, you have to have revenue, right? You have a burn rate, that's not changing. So you've got to have revenue to offset that, or you're shortening the time horizon until your next fundraise. So I think you have to have an honest conversation about that. And then the sales team needs to run a diagnostic. You have to get to root cause analysis. I would think that in general, coming out of that, you're going to uncover places in your sales process that are not well tuned, that you can fix. And the sales team is also probably going to have legitimate feedback about where the product's not working. And then the CEO, it's up to you to determine whether or not you think that those product gaps are ones that belong in your roadmap. And if they do, then you've got to give the sales team

• 30:49Speaker 03

  a little bit of credit that maybe they're not winning because the product needs some things. Or you've got to say, the things you're saying we need to win are outside of our product roadmap, in which case we have like an ICP problem of who we're actually targeting and talking to, and how do you go fix that, right? So I think what often doesn't happen when sort of the founder and the sales org don't operate effectively and ultimately fire your head of sales, right? Is did you get to a root cause analysis that you can agree or not agree on of what's causing that gap?

• 31:19Harry Stebbings?

  Yeah, no, I totally get you. In terms of the flip side, you know, you're at Stripe. Stripe is obviously a phenomenal company, scaling like very few ever have done in history. Is it ever a challenge where it's almost too easy? Where there's too much confidence? And you have to say, hey, every day, we're still fighting, we're still competing. Is there ever the flip side where there's too much confidence in the sales team?

• 31:39Speaker 03

  I don't think we've had that. Mostly because where some of the confidence can come from is if you've had strong organic growth, but the company still desires to have very high growth rates. There's often going to be a point where the organic growth of your business is divergent from your growth rate aspirations because the numbers just start getting pretty darn big. And so I think that's been the challenge at Stripe. Realizing when kind of what got you here won't get you there. And you now actually need to lean into spending more money on marketing or hiring. Other types of resources in support of your sales organization because you're now having to pursue a different portion of the market or utilize a different go-to-market strategy than

• 32:23Speaker 03

  you had to for, say, the last five years.

• 32:26Harry Stebbings?

  Totally horrible unfair one. Is traditional outbound sales dead?

• 32:29Speaker 03

  Oh, definitely not. It's not. I think tactics are changing and it's true that people are educating themselves more and so they're coming to you at a different portion, maybe in their sort of education and evaluation maturity. You know, everyone out there is doing cold calling, emailing, et cetera, right? So the average decision maker is getting inundated relative to the past. But if you're just sitting there hoping that your marketing org is going to drive you inbound demand, you're probably growing at a slower rate than you could be otherwise. And if you look at the companies that are the largest on the planet, most of them have a strong prospecting organization.

• 33:05Harry Stebbings?

  I do want to move into my favorite, though, which is a quickfire answer. I say a short statement and you give me your immediate thoughts. Does that sound okay?

• 33:11Speaker 03

  Sounds like a plan.

• 33:12Harry Stebbings?

  So, I mean, what sales tactics have not changed over the last five years? What is still core?

• 33:18Speaker 03

  I would say, one, I'm hesitating because COVID has changed us a little bit, but there's real value in connecting in person. There are things you will not uncover over a phone call and Zoom. Two, I would say, is just a well-architected sales process where you understand the stages that a deal goes through and the exit criteria associated with them. And three is being able to quantify the thing you're selling. I promise your sales cycles will have more velocity to them if there is legitimate ROI associated with what you're selling.

• 33:46Harry Stebbings?

  What sales tactics have died a death on the flip side?

• 33:49Speaker 03

  I do think there is more of an ability to shift online and have a digitally oriented sales process. So that's a key one. You know, more tools within the sales process, much more data orientation, I would say, rather than, you know, there are 10,000 companies to pursue, less as a result, higher 1,000 reps and just, you know, give them the yellow pages and see what happens.

• 34:14Harry Stebbings?

  What would you say is the biggest mistake that you see founders make when hiring sales teams?

• 34:18Speaker 03

  Lack of ensuring cultural alignment. Related to that is like really incorporating your sales team into the rest of your org.

• 34:26Harry Stebbings?

  Thing that worries me is that we raise so much money so soon now that we hired 20 sales reps before we have any repeatability and we have no product market fit even. And then it burns culture and then we get in this vicious loop. But then that's just a consequence of having too much money in this ecosystem. I was called OK boomer the other day by Bill Gurley. I was like, ouch, that's really a worrying sign.

• 34:45Speaker 03

  I think your concern is better than mine.

• 34:48Harry Stebbings?

  Tell me, I'm a sales leader. What one piece of advice would you give me starting a new role today?

• 34:53Speaker 03

  Like a seasoned sales leader or a new sales leader?

• 34:56Harry Stebbings?

  New sales leader.

• 34:57Speaker 03

  First time sales leader?

• 34:58Harry Stebbings?

  First time sales leader.

• 34:59Speaker 03

  First time sales leader. I would say understand your operating model. So really understand your funnel, understand the assumptions you are making about your funnel, deal size, conversion rate, et cetera. Make sure you're measuring that and then use that as a way to fine tune your engine.

• 35:14Harry Stebbings?

  What would you most like to change about the world of sales today?

• 35:17Speaker 03

  I would like to change sales comp. I just think it's still, and it's so hard to change, but I just think a lot of it is still a relic of how sales worked 20 years ago. And I think there's like a huge opportunity to be more innovative in the metrics, in the integration of cash and equity. I would love to do that differently.

• 35:36Harry Stebbings?

  What's the hardest element of your role with Stripe today, Jean?

• 35:39Speaker 03

  Honestly, like we're hyper growth and I think our, the underlying tool, systems, operations haven't scaled as quickly as we've scaled salespeople. Data, rigor, velocity, those all hold us back.

• 35:51Harry Stebbings?

  Final one, what one company's sales strategy other than Stripe's have you been most impressed by in the last few years?

• 35:57Speaker 03

  You know, our CRO comes from AWS and I do think that they've been very thoughtful in having a data-driven, you know, well-architected sales process in a consumption-based world. And so I appreciate that.

• 36:10Harry Stebbings?

  Jean, listen, this has been so much fun. I'm sorry for going completely off topic in some areas, so I really appreciate the patience, but I've loved having you on. So thank you so much for joining me today.

• 36:18Speaker 03

  Likewise, it was awesome. Really appreciate hard-hitting, very pointed questions. Hopefully folks get a thing or two out of this.

• 36:27Harry Stebbings?

  I just love that discussion with Jean and what I like so much about these shows is how granular we go, not just stopping with the first question, but really going deeper and deeper into the interview process, the questions to ask. If you'd like to see more from us behind the scenes, of course you can on 20vc.com, that's 20vc.com. But before we leave you today. Salesloft is the leading sales engagement platform, helping sales teams drive more revenue with the modern revenue workspace. It's the one place sales teams can go to prospect, manage active deals and get the insights they need to coach seller performance, forecast with accuracy and find out what steps to take to close more deals. Some of the world's leading companies like IBM, Shopify and Stripe all love a new Salesloft and so can you. It's the new way to sell and find out more today at salesloft.com.

• 37:10Harry Stebbings?

  And founders, if you've got recurring revenue like so many of you have, there is a smarter way to grow your business. As a VC, this pains me to say, Pipe is a completely new way to finance growth without taking on restrictive loans or diluting your ownership. If you have proven product market fit, your recurring revenue streams could be your biggest asset. Pipe is the world's first trading platform that turns your recurring revenue into upfront growth capital within as little as 24 hours of being connected. It's fast, flexible and founder-friendly and they also work across many industries from SaaS to direct consumer subscription, media and entertainment and many more. And with Pipe, there are no loans, no dilution, no warrant coverage or restrictive covenants. Pipe is growth on your terms and right now 20 sales listeners get trading fees waived for 12

• 37:54Harry Stebbings?

  months, which could save you tens of thousands of dollars depending on the size of your business. Sign up today at pipe.com/20sales to start trading today. And finally, to scale your business, you need customers. But this CRM software model is 35 years old and it's never evolved to properly support modern businesses. Most legacy platforms were built for a single rigid repeatable sales process. But guess what? Copper is a dramatically different kind of CRM. Built for Google Workspace businesses, Copper works right alongside you in your inbox and it's so flexible and versatile that you'll love it regardless of how you run your business. Plus, it requires virtually no training because it works just like all your other Google apps. Get set up in less than a day and easily customize your CRM to fit you.

• 38:35Harry Stebbings?

  Your needs. I promise you this will be the first time that your team love you as a leader for choosing a CRM solution. That is a personal experience of mine and so see why more than 30,000 businesses love Copper. A flexible CRM that grows with you. Get a 20% discount on any annual plan. Just go to copper.com/20vc. As always, I so appreciate your support and I can't wait to bring you a fantastic episode this coming Friday.