The Stripe Sales Playbook; Who Should Create It, When Should it Be Done, Where Do Many Go…

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

So I started off looking up to my father. He worked in tech, so he spent seventeen years at IBM, was one of the first people to sell the PC. He just had this really dynamic career. think 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 you 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 gonna do. I wanted to come back to the Bay Area. I wanted to have a dynamic and And he really got me to think about tech.

I landed at Stripe because Claire Johnson, our COO, was my first boss at Google back when I was, you know, directly out of college. So when she joined Stripe, I frankly 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. A couple quarters after that, gave her a call and was like, I think I might wanna come and chat with you. and was in her office within, I think, about forty hours and six weeks later had a Stripe offer in hand.

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 gonna 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 bring in somebody who has good sales skills in this area.

Yeah, I think bringing in a sales team often probably should happen 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 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 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.

Yeah, I agree. I think you want 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, true versus sort of a single individual’s point of view.

But two to three people versus going out and hiring 1020 twenty 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.

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 deep in your product, geek out on it, can articulate the vision and the product capabilities in line with how a founder would. Which is very different than hiring somebody who maybe has worked at Salesforce for the last ten 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 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 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 ing the organ.

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 was like a good way to separate who was like really a startup salesperson from somebody who was a salesperson 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, you know. So if they can do that before they’ve even shown up, probably higher likelihood that they’re to succeed.

In it. So look, you’ve got to sell your startup first. So you to, you know, it’s equal parts. The first one or two calls are 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 twenty four 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.

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 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, you know, how you’ve gotten into an account that was totally pulled, 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.

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, etc. 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? You know, ditto on sales. People talk about, oh, you know, we just do this really tight sales process with seven steps. Well, 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.

Yeah, this is something I was really impressed with at Stripe when I started. So for a company of the scale we were at that point, it was a full week of just spin up. And you had sessions with John and Patrick where they were really 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 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 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, 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 thirty days, I just went out, figured out, you know, where there were patterns, and then started to put in what I thought was going be our sales process 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.

Your first week at Stripe right now is very pan Stripe. So actually salespeople are with product people, with engineers, folks in recruiting, etcetera. 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. 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, 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 essay 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 thirty days.

And then, you know, we really start getting into what’s it going to take to hit your number? Are you talking to enough people? You know, are you actually developing opportunities, starting to progress them further in sales process? One of the things I think Stripe does a really nice job of is having spin up buddies. So for the first ninety 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 ground.

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, then we started increasing leverage, moving things more towards individual, you know, etcetera.

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 ninety 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 can be pretty discerning of is this person rapidly grokking 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, need to close this many deals of this size and take, you know, you win at this rate, it takes this amount of time. And so you actually can be able to tell your salesperson by ninety 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.

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 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?

Are they still sort of just showing up every day and doing what’s in front of proactively driving towards the outcome. So a great rep typically would come to me in a one on one and say, Jeanne, my target is X. I’m going to need to close 20 deals to hit that. 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 keep you at arm’s length because the best ones typically know where they can leverage other people in the org and really want do that.

Yeah, I think one of 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 moment. But you also want to use product efficiently. So I think we’re thoughtful around having some level of gating so that 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. And then from a customer success perspective, 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, 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 downstream lives easier. But then similarly, when you got things downstream, we really need customer success showing up so that the sales team can continue to focus on driving revenue.

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 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, unsuccessful. So typically it’s that you haven’t actually sussed out the customer’s ability to deploy and ramp with your product.

You got to dig below the pitch deck. You know, You can convince a customer that your product’s going to be valuable, but then you also need to make sure that they really can execute execute it. So I think that’s where sometimes sales and customer success can struggle and customer success can feel that 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.

Yeah, so it’s definitely, it’s different, right, than a company that’s like hardcore enterprise sales hoop to net. 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 serve 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. And so I think it’s just important to remember product led growth can be awesome for a certain portion of the market. if And 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.

Oh, yeah.

Yeah. So, I mean, it’s very typical sales practice to do loss reviews. At Stripe, we actually purposefully So Stripe 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 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. we actually call it that where before you’ve lost the thing, you know, your 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 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 more broadly and try to find, again, patterns, themes, and what you would do differently.

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 Salesforce loss reasons, those types of things, you wind up with like clear go to market challenges where our messaging, our strategy’s 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 of those and they influence product roadmap and then obviously go to market changes as well.

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 Dialpad, 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 70% 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, I know that we all consider this a stretch. And so for 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 because we built a full operating model what needed to be true underneath that and how audacious some of those goals were. And that was something I missed, I think, in how he and I were communicating and understanding where we thought, this is just, we 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?

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

Yeah, I think it’s more empowering. One, 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. 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 a little bit of credit that maybe they’re not winning because the product needs some things. Or you got to say the things you’re saying we need to win are outside of our product roadmap, in which case we have 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?

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

Oh, no, 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, etc. 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.

Sounds like a plan.

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 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.

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, let’s as a result hire 1,000 reps and just, you know, give them the yellow pages and see what happens.

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

I think your answer was better than mine.

Like a seasoned sales leader or a new sales leader?

First time sales leader.

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

I would like to change sales comp. I just think it’s still, it’s so hard to change. but I just think a lot of it is still a relic of how sales worked twenty 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.

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.

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

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