Operators Ep 28 Transcript

Delian Asparouhov:

Hi, everyone, my name is Delian and I'm a principal at Founders Fund, a venture capital firm based in San Francisco. This is Operators where I interview non-VC, non-CEO, non-founder operators that make the startup world go round. Today I'm interviewing Jeanne DeWitt Grosser, head of America's revenue and growth at Stripe. Prior to joining stripe, Jeanne was a CRO at Dialpad and spent over seven years at Google prior to that. I hope you enjoy the show. Sweet. Well, Jeanne, thanks so much for coming on the podcast, really excited to have you on today.

Jeanne Dewitt Grosser:

Thanks for having me.

Delian Asparouhov:

Well, with these types of conversations, before we talk too much about Stripe, I'd love to dive into the earlier stages of career where you actually started off at Google in 2004, in an ops manager-type role. Can you talk a little bit about how you ended up there, after getting a BA at Duke?

Jeanne Dewitt Grosser:

Yeah, absolutely. My father had worked in technology. growing up, I got to see him travel all over the world and I always found the conversations he would have about it really interesting. That inspired me to want to go into tech post undergrad, which at the time, it's just so weird to contemplate this, but that wasn't a normal thing to do. I don't know that there was a single other kid from Duke that year who went to Google. Times have certainly changed. Then I just got lucky in ending up on Gmail. I applied actually to try to be a junior sales person in ads organization. For some reason, they plucked my resume out of the queue and stuck me on this to be launched product, Gmail. When I was interviewing, they literally had to send me an email invitation to my AOL account. Again, that's what we're talking about.

Jeanne Dewitt Grosser:

I wound up on that team, joined the product two months or joined the team two months after the product had launched and was literally answering support tickets, people asking, "Are you reading my email? Why does the email product not have a contacts list?" which believe it or not, Gmail did not at the time. This is also before the days of Zendesk, right? You're manually answering all these emails in a fun little tool called tracking that we had at the time, but that was how I got started at Google.

Delian Asparouhov:

Wild, I remember that first big Gmail announcement. Invites went crazy, so I'm sure that team was going through quite the heyday.

Jeanne Dewitt Grosser:

$200 dollars on eBay to get an invitation to a free consumer service.

Delian Asparouhov:

That's absolutely wild. You ended up staying there for about four years and then decided to go to grad school at Stanford. I guess, what made you want to go get your MBA, and then ultimately also, what brought you back to Google in 2010? I'm sure there's a pretty interesting time to be going through an MBA program during this financial crisis and then out on the job market afterwards, so what was that all like?

Jeanne Dewitt Grosser:

Certainly, what had happened was, I joined Google and Google went through this rapid period of scale. During that period, the problems we were solving were increasingly complex and more ambiguous. It wasn't obvious what the answer to them would be. When I looked around me, there are a lot of leaders that I really admired who were just great at breaking down really complex problems. I felt like they had a set of skills that I just didn't have yet and wasn't learning as rapidly as I wanted to on the job. In most of those cases, they all had MBAs. I also at the time, I think how I went and state my goal is like, "My goal is to be the CEO of a company equivalent to Google, but not Google because I knew I would never get that job."

Jeanne Dewitt Grosser:

I thought it would be a good idea to go learn a thing or two about finance, accounting, some of the other functions I didn't have any insight into. Left to go get my MBA. Literally, so I left in 2008 pre-financial crisis, so actually the peak of the economy was buzzing. I cried the day I left. I really had no desire to leave Google at the time, but I felt that if I looked at where I wanted my career to go over the next decade, this was something I had to do to get to where I wanted to go. It actually was always my intent to come back to Google because again I didn't want to leave, I just felt like it was an Important to do this. I was super fortunate at the time Google did have an educational fellowship program. I actually stayed an employee of the company while I was on educational leave.

Jeanne Dewitt Grosser:

It was always my plan to come back, although I had entertained the idea that I might not if an interesting enough opportunity arose, but when I looked at graduating, one, decent chunk of my classmates were dying to get in to Google and here I had my path right back into it. I just felt like my learning opportunity at Google wasn't over. They were doing really interesting things, operating at the scale where you would learn unique approaches, but I can also work on a newer product which was something I'd always focused on at Google, working on the "startup" within the big company.

Jeanne Dewitt Grosser:

I switched over to what at the time was known as Google Apps in what ultimately became the Google Enterprise Organization into a sales capacity. I did that because while I really enjoyed working on Gmail, I always described it as you were like playing with funny money, right? We got to piggyback on the millions and billions of dollars that Google was minting. You didn't really have to build a business. Since again, I wanted to be a senior leader at a company, it seemed pretty darn important to learn how to actually build a viable business. That was why I moved over into what's now G Suite to learn more about that.

Delian Asparouhov:

Jeanne, you came back and you started in G Suite, SMB sales and ops. Give me a sense of the status of G Suite at the time. What was the initial scope and what you were focusing on? It sounds like, in particular, you're focused on channel sales and driving freemium strategies. I'm sure we're talking about 2010 where it's like Salesforce has clearly proven out this software as a service business, but it's not like this playbook was super well defined how I'm sure even the world of like freemium wasn't even that well known or widely known of an idea.

Jeanne Dewitt Grosser:

No, not at all. I would say Salesforce had demonstrated that SaaS was a thing, but honestly, the unit economics of SaaS were really not well understood. I went on a little bit off tangent here just because I think it's such an interesting case study. This SaaS as an industry is now incredibly mainstream, we're over a decade into this, but at the time, you're core LTV to CAC payback period around SaaS businesses really wasn't well understood, right? A lot of SaaS businesses don't look all that attractive in the first couple of years, but then you hit this inflection point where your install base is big and just nicely printing money for you often with positive net retention and that offset CAC of the new customers you're acquiring.

Jeanne Dewitt Grosser:

Honestly, Google didn't understand that. The SaaS revenue model looked pretty darn different than the ads revenue model. In particular, when you think about an enterprise customers within ads, you have a shorter payback period because they can be like, "You know what? I'll give you 100k. If it goes well this month, then awesome, we'll turn that into a million next month," and so just has this really positive feedback cycle particularly when it comes to customer acquisition, whereas enterprise software doesn't have that. When Google looked at enterprise software, I think they looked at it as being like, "This is really darn expensive. You've got some established incumbents like Microsoft. Is this going to be an interesting business?"

Jeanne Dewitt Grosser:

It's sad to me because we were so well positioned to win, in my opinion, in 2010, through 2012 if Google had recognized that sooner and dropped $100 million into it, and instead, we let a lot of the competitors catch up and in some cases even really surpassed us. Now, Google is, in many cases, coming from a position of second or third and trying to overcome that. Anyway, at the time, I was serving the littlest guys, so small and medium-sized businesses and we had a really interesting dynamic where we had this freemium strategy. We had a midmarket business that was on fire, 300% year-on-year growth and then we had a small business that was flat year on year. That was what I was in charge of, is like, "Come in and make it grow again," and so really dove into our freemium strategy and some of the problems that was producing and change that and a year later had it growing triple digit.

Delian Asparouhov:

Then from there, beyond just working on the SMB side, you started to expand into international initially in Japan, Asia-Pacific, but then eventually into midmarket in North and Latin America. I'm sure SaaS was only just becoming a thing, more widespread the United States, but let alone convincing companies internationally to spend significant amounts of software subscription. I'm sure there's a whole other challenge, I guess, and I'm sure related to work that we'll get to at Stripe since Stripe obviously is a very international company. I guess, can you walk me through a little bit about some of the challenges that you had to face especially in some of this international expansion?

Jeanne Dewitt Grosser:

I took the role running APAC because I aspired to ultimately be a global leader. When I looked at global leaders, one of the things I was surprised by is actually how few of them have international experience. I thought it was really important to actually go have international experience, so that I could have appropriate empathy for what it means to work outside of headquarters. Let me tell you, it is pretty darn different. There's two sides of that coin. One is just actually put the market aside for a second, actually working there, it is so jarring to have to do your job. Most APAC leaders have to get up at 5:00 in the morning multiple days a week to get on staff meeting, forecast calls, etcetera. Literally the 18 months I was out there, I took a forecast call at 4:30 in the morning my time on Wednesdays and I took a staff meeting call at 5:30 in the morning.

Jeanne Dewitt Grosser:

In both cases, my boss was like, "You're more than welcome to not do this or to do it every other week," but if you want to be in the know and relevant, you got to do that. Our folks in EMEA have a similar experience where it's like, 4:00 PM their days nearly over and all of a sudden their email just has blown up by all the Americans coming online, right? You don't know what that feels like until you have done it. I really think all American leaders who ever want a global role should be forced to do an international stint. Let's like [inaudible 00:12:07] that part. Now the market. The market is also like you can read all the analysts' reports you want, you will never comprehend any international market until you have gone out and seen it firsthand. There are a lot of interesting dynamics.

Jeanne Dewitt Grosser:

Often what happens is those markets can be either behind or in some ways ahead. As an example, when I went out to APAC, really in the US, we've started to overcome concerns about the cloud in general. When you were selling G Suite, you didn't have to convince people about the cloud anymore. You just had to convince people about the superiority of our product in the cloud, whereas when you went to Australia, people were still super uncomfortable with the concept of security, "Giving you my data." You actually have to sell the cloud before you could even go sell your product.

Jeanne Dewitt Grosser:

Then in other places, in other parts of Southeast Asia, you had a different dynamic which was a lot of these companies had never had on-prem services, right? They were getting online for the first time. Then you have a different approach where they're almost doing a technology skip and so it's really actually interesting. I think anybody who's run APAC in particular, it's crazy to think of it as a region because Japan to Australia to the Philippines, these markets really couldn't be more different. A lot of what you have to do is learn how do you understand and have a strategy for a place that has a lot of nuance.

Delian Asparouhov:

Jeanne, can you talk through maybe some of the more impactful projects that you've worked on while you're there? It sounds like there's out of restructuring, sales strategy, local pricing changes to adapt to local expectations. Can you talk through maybe a process to these regions, maybe one or two of the more impactful projects that ended up leading to international success?

Jeanne Dewitt Grosser:

Absolutely. Google at the time was pretty darn direct sales oriented. In Japan, anybody who's worked out there knows that that tends to be more of a channel-oriented country. In Japan, we basically had a direct sales organization and the other thing is it's a very face-to-face culture. It's not really an inside telephone sales, yet that's what we were doing because that was what was working in the US. One of the things I did out there was we had a really successful partnership in the enterprise space with SoftBank Telecom and so worked with my team to actually help SoftBank understand the opportunity in the SMB market and get them to spin up a team to support selling Google Apps through their channel.

Jeanne Dewitt Grosser:

That was a big one where we basically have to say, "As successful as this inside direct sales, online sales actually, motion is in the United States, that's not going to be successful in Japan. We got to go spin up this channel." Another good example was India. Our price point was ridiculous. At the time, there's a bunch of quantitative things you can use, but a simple one was the Big Mac index which is like, "What's the relative cost of a Big Mac in different countries?" and you use that as a benchmark for pricing. We were literally like five plus X what we should have been and so did a major pricing overhaul which enabled us to then drive online scale.

Jeanne Dewitt Grosser:

Now the thing that was really interesting about that, and something I overlooked, was I was very focused on the SMB market and needing to set up this self-serve online channel. The other thing that's true about India is it is a very discount-oriented culture. People really want to feel like they got a deal. In changing the price to enable scale for the SMB segment, we actually created some problems for the enterprise space who actually ultimately priced at the price that we went with online, but now we had crushed their ability to offer these attractive-looking discounts. That was a good learning and how you always need to think about your business holistically beyond just the portion that you personally are responsible for.

Delian Asparouhov:

I guess speaking of thinking about a business holistically, your next role after being at Google for almost eight years was joining as the CRO of this company, now back in San Francisco, Dialpad, and obviously, this CRO role, you have to think about the business like much more holistically. There's only a year long, but I'd love to hear, how did that opportunity come across your plate and what were some of the interesting learnings to now having perspective of dealing with all parts of a business?

Jeanne Dewitt Grosser:

This, how I got this role is a good story and the power of your personal network. Basically two things, one was actually in, I think it was 2006, Google acquired Grand Central which became Google Voice. The guy who ultimately became the VP of product at Dialpad had been the product manager for that at the time and he and I had interacted, not super deeply but enough for him to know me and have a sense for my work. Then the founder of Dialpad was very close to Dave Girouard who had been the original president of Google Enterprise who also knew me and my work. Basically, I got on their radar via those experiences with me. I talked to Craig and the Dialpad team. They weren't called Dialpad at the time actually, it was just UberConference, probably for nine months before I took that job, which I think is an also good insight for folks.

Jeanne Dewitt Grosser:

At the time, I wasn't sure that they were at a stage where I was going to be most useful, when it was just UberConference. He was figuring out the role and it wasn't exactly the CRO role that I wanted, but I felt like there was something interesting there. What I did was, every four to six weeks, I'd shoot Craig an email about some article or something relevant that had happened that I thought could apply to his business and passed along an insight. He and I maintained this dialogue for nine months. Then finally, he came back to me and said, "Hey, we're going to launch this product, Dialpad, and I actually think the CRO role would be great for you." That was when I decided to make a switch.

Jeanne Dewitt Grosser:

That one was super interesting. You talked about getting broader business insight. When I joined, they hadn't named product. I literally joined having seen a prototype. There was no website and we hadn't thought through positioning. Literally nothing was done and like by the way the product was supposed to launch 75 days after I joined. We were in the Google Ventures office doing like branding sessions. We're trying to figure out what to call the thing and then a lot of work done to map out positioning, where we thought we were going to sit in the market, what that like imply for the different features we were trying to highlight and carve out a space for us. I had an opportunity to really start building this marketing muscle.

Jeanne Dewitt Grosser:

One of the things I was very passionate about was having an aligned strategy across sales and marketing because I just so frequently see orbs where sales and marketing, they're both go-to market yet they have these overlapping but not the same strategies. That was one of the things I was passionate about building. Then the other thing that that role gave me the opportunity was to help fundraise. Craig and I drove the Series C investment and that also gives you a whole other perspective on what are investors looking for, what are the parts of our narrative that we have down path versus we didn't know from a sales perspective. You learn how to sell the vision of a company rather than just a product. That was all interesting too.

Delian Asparouhov:

Was there anything that you talked about how it's just so different, I imagine, selling something that is coming to life versus G Suite which is an already preexisting beast, that you were just figuring out the go-to market wishes for. What was the maybe biggest hiccup or thing that maybe didn't translate going from Google's not quite a big company back then, but it was definitely obviously much bigger than nascent startup? What didn't come as naturally?

Jeanne Dewitt Grosser:

Absolutely. I'll tell you one story that's not going to entirely answer that question, but still fun and then I'll give you another direct answer to that. One of the things that was awesome in this role was, like I said, when I started, the product was not fully shippable and we had this amazing opportunity with Motorola Solutions. Google was in there trying to sell them Google Apps and compete against Office 365. Office 365 had link. Google didn't have anything from a voice perspective and so they said, "Hey, can you guys come in and help fill this product gap for us?" It's my second week on the job and I literally flew out to Schaumburg, Illinois with nothing more than like a pitch deck. There was no product. Here we are trying to sell a 20,000-person global company on literally slideware.

Jeanne Dewitt Grosser:

One of the interesting things of that and it relates to your question is so they got really excited, "Nice slides," and as we're going through the sales process, probably a month in, I finally had to sit down with them and say, "I'm really excited you guys are excited about our product. I think you will never sign our contract. We do not have the legal and security constructs that I know you're going to want as a traditional enterprise and we're not going to be able to have them. We should talk about that now because it won't change. You're either going to have to get past that or we should probably call it." Ultimately, the solution was interesting enough to them that there were some things we wound up building and figuring out and then there were some things that, honestly, I have no idea [inaudible 00:22:41] sign the contract because Motorola certainly want them.

Jeanne Dewitt Grosser:

Anyway, six months in when we just barely had a product, we actually signed that deal, but then the other thing on your question was so going back to fundraising, of course, one of things you do is build a revenue model. We were building a revenue model for a product that was going to go to beta about two months after we were trying to close the round, so you had no data on how it was going to perform. When I built the revenue model with the head of finance, basically I knew the Google Apps conversion funnel called and we were going to start by selling to SMBs, despite this Motorola monster enterprise that we were working on.

Jeanne Dewitt Grosser:

I knew all those analytics Coal and so I was like, "Okay, I'll just apply that funnel here and I'll take a haircut," because I realize I don't work at Google. Well, the haircut I took probably should have been an order of magnitude larger. Suffice to say, the level of inbound demand that Google can generate, given its brand and its ability to pour a little bit more money into ad spend was not what we had. We had to refine a couple of assumptions after we started getting the first few months of data.

Delian Asparouhov:

That's hilarious. I did not realize that slideware was a term, but I like that term for software that's not quite been built out yet, you're really just pitching it. Cool. Well, sounds like from there, you ended up switching over to Stripe as the head of North America sales. I would love to kind of hear how that opportunity came about and what the decision making process was around Stripe. At the time, they're not super late stage, but I think slightly later stage where Dialpad was out right there, maybe Series D at the time roughly, but I'd love to hear how that came about.

Jeanne Dewitt Grosser:

Another example of the power of network, so Stripe's COO, Claire, had been my first boss at Google. When she joined, she gave me a call. Unfortunately for me, I was happy at Dialpad at that point. We connected, but I told her I'd call if anything change. Ultimately, I followed up with her and wound up with Stripe. At the time, Stripe was about 400 people, about six months into having any sales organization. I joined, I ran a 10% team of account executives with the remit of, "Go figure out how to grow this." Here we are, we can talk through a bunch of the things along the way, but five years later, that's a little north of 300 people. Probably figured out a thing or two between then and now.

Delian Asparouhov:

Maybe as a little interjections/Easter egg, thank you so much for training up our dear friend, Eric Lasker who has now joined my company as head of BizDev in Federal ...

Jeanne Dewitt Grosser:

Awesome.

Delian Asparouhov:

... for quite some time. He says hello.

Jeanne Dewitt Grosser:

Eric Lasker is the best. He still actually owes me a dinner. The guy's quite a chef.

Delian Asparouhov:

He is quite a chef. He has a unique background and that he has a physics and quantum background, is a chef, also worked at Stripe in BizDev for five years and understands the aerospace world. He is head of Federal at Zipline. In some ways, I joke that he was forged in a kiln to build to work at my startup. I'm very excited that we got him and thank you for training him up, but I would love to understand a bit of some of the more impactful projects, and maybe some of the scaling challenges along the way. I'm sure going from 10 to 300 always is a bit messy. Maybe some of your more exciting areas, especially around recruiting and scale up as well as making data-driven, sales-related decisions around how to structure teams, comp, where to go to market, etcetera.

Jeanne Dewitt Grosser:

Yeah, all right, well, that's a lot to cover. Let's see. A couple things maybe tactically that I might highlight for folks. One of the first things I did when I came in was to build out what I would call an operating model. Company walked and have your top down revenue model, "We want to do 10 million ARs," whatever that number is, but a lot of people forget to build the bottoms up part, which is what actually needs to be true for us to get 10 million in revenue. When I joined, Stripe didn't have that model. One of the first things I did was to get data on our current funnel. We were very inbound driven, "How many inbound leads are we getting? What's the average size of them? What's our win rate? How long does it take to close? How long does it take to go live?" that whole end-to-end funnel.

Jeanne Dewitt Grosser:

Then basically from that, you can say, "Hey, if history is going to be predictive in the future, I think I can cover this much revenue with what's happening organically and what do you know?" We had a revenue target that was higher than that, so then you start asking yourself, "Okay, well, within this equation effectively, what are the levers that I can pull that would increase revenue?" and so then you break apart each chunk in that equation. One of the guys on my team jokes that this is the Jeanne version of conjoined triangles of success but I had this equation slide I always show people with a bunch of shapes on it, but it's not rocket science, right? It's just funnel math, but not enough people do it at the outset.

Jeanne Dewitt Grosser:

"On each part of that funnel, okay, well, how do we get more leads? We had a one-person marketing team, so it's probably not going to be through marketing spend. That means it's going to have to be outbound, right? What's going to be our prospecting plan? How do we do that?" Average deal size, we were working pretty darn small deals, so that meant you were going to have to do lots and lots and lots of them or you're going to have to work bigger ones. That was where we developed a strategy that I've talked about in a couple other places around buffaloes, which were basically like a Series C, D company. Those, you can go to Crunchbase or wherever and just be like, "Let's go get a list of all the Series C and Series D companies. Let's go put them on a prospecting list, work on that." Similar things of like, "What can we do to drive our conversion rate?" We didn't have any sort of sales process.

Jeanne Dewitt Grosser:

Now you go take a bunch of calls yourself, get in the trenches and then go talk to all of the account executives on the team, "What's working? What do you talk about? Who do you talk to?" and try to [processize 00:29:39] that into things that we can repeat and then learn from. That was the first thing that I did because what you're trying to get to as a revenue leader is basically with confidence being able to say, "If you give me X dollars today, I can promise you Y dollars by this point in the future. As long as that holds true, you should probably keep giving me X." That was what I was seeking to do.

Delian Asparouhov:

I definitely think the best executives manage their entire business just as like a math equation. It's just you start to understand what the inputs and the outputs are and figure out which levers are the most easiest to pull. I'd be curious, I think one of the things that Stripe was always, let's say, famous for in the early days was the "call us and install," right? Patrick and John would come over to your house and install Stripe for you. More well-known early on for hyper small startup and scaled with it, but it sounds like your team started to think about expansion in enterprise which is obviously a very different go-to market motion than the two founders, showing up in your house and go through your installation, the installation on a "buffalo." I imagine it's a bit more complicated than Patrick and John just sitting down at your kitchen table.

Delian Asparouhov:

I guess can you talk through some of the challenges of that transition of going from primarily SMB and bottom up driven to actually doing some level enterprise top down and not only the go-to market motion for it or the sales motion, but the actual, I assume, post-sale actual implementation, technical success, I imagine it's much more complicated than those types of implementations.

Jeanne Dewitt Grosser:

Absolutely. Certainly two things that I think would be helpful for people. One was, as you move up market, that's where role specialization becomes that much more important. One of the things I was really surprised by when I joined Stripe was we saw an API, we didn't have a single solution architect to the company, and mind blown, couldn't figure this out. Part of it was we'd hire these wicked smart account executives like Lasker who could go learn things about the API and actually be more somewhat credible with a developer and you have the dock. They'd be happy to go do that, but as you move up market, you're ripping out an existing architecture.

Jeanne Dewitt Grosser:

In order for companies to feel comfortable that they can do that, you have to be able to understand their current architecture and map it to what their architecture is going to look on Stripe to derisk the project. That was one of the things we had to start adding was solution architects as well as implementation engineers or integration engineers. Solution architects were during the sales process to give them confidence that, "Yes, if you sign a contract with us, you will in fact deploy and then the integration engineers were ... The other thing that's true about enterprises is while developers at startup like docs and being like choose your own adventure, "I want to go figure this out myself," enterprises don't want to make a mistake.

Jeanne Dewitt Grosser:

They basically would come to us and say, "Jeanne, our business model as a marketplace, you guys have deployed and emailed 100 marketplaces. What's the best way to do it?" We'd be pretty annoyed when we wouldn't be able to say, "Here's the template." We had to start doing documentation more oriented toward product managers as an example and slightly less technical audiences. That was one set of things. The other thing I'll say that I think is helpful both for the founders as well as the go-to market leaders trying to help drive up market was we were very, very thoughtful about trying to pursue the enterprise in a way that capitalize on what Stripe was good at.

Jeanne Dewitt Grosser:

In day one, we weren't trying to go out and win your most traditional enterprises because doing so was going to require building out a systems integrator, function much, much more rapidly, scaling some of these technical and post-sales functions I've discussed and a lot of the roadmap requirements were going to be pretty far afield of Stripe's core roadmap. What we tried to do was, as a go-to market team, say, "Here's Stripe's core roadmap. What are a set of larger companies that would find that their solution would be 80% covered by what we were doing already and the incremental 20% that we would need to build would also be applicable to all of these startups that were growing up on Stripe?"

Jeanne Dewitt Grosser:

That way, because the risk sometimes run with enterprise sales is unless the company is super aligned that, "We are an enterprise company and that's what we're going to do," is you can create this bifurcation between the sales organization and the product organization where the product team gets annoyed basically that sales is signing these super attractive deals, but we don't actually have product for them. We try to really ensure that we were pursuing the enterprise market together.

Delian Asparouhov:

What do you think Stripe did that married this well? I will say I feel like when I talk to product folks at Stripe, I feel like they have a much deeper understanding of down to each individual customer's needs, priorities, how the roadmap actually solves those needs. What do you think Stripe does uniquely well in terms of integrating the product team and their priorities and feedback and integrating the sales team's priorities and feedback into a single and cohesive roadmap? What do you think Stripe does that so well?

Jeanne Dewitt Grosser:

It's a number of things, but one I would say is our first and foremost operating principle is users first. That is just really culturally embedded in the company, is the take is basically it's unlike the saying of the Ford one, right? If I went and talked to customers, they would have told me to build a faster horse. A lot of tech companies have that point of view which is like, "Our end consumer is unlikely to give us useful feedback, right?" Stripe doesn't have that. Our take is businesses acutely understand their problems. We may figure out a better way to solve them, but we need to deeply, deeply understand their problems. The only way to do so is to talk to them. Part of the way in which this gets inculcated into the culture is the executive team are all incredibly user facing. John, Patrick, Will, Claire, all of them talk weekly, daily, honestly, to different customers of ours. That expectation really cascades down to everybody else.

Jeanne Dewitt Grosser:

Then the other thing, I do think is because sales was very careful to stay product centric, we haven't felt like this adjunct. We've always been very ingrained in the company culture and the way the company operates. I think product and sales natural align and product has found sales to be some of the best R&D research that we have at the company. Now as we've scaled and you've got a lot more customers, you're serving a much broader suite of products, it gets harder to get all the feedback into a place that you can really prioritize. We now have a product operations organization. They've built out a bunch of infrastructure to both capture lots and lots of data, whether it's through Salesforce, customer surveys, etcetera and get massive data points as well as go individually out to the teams, so that we can get literally 1000 data points on customer needs, but then narrow those in to what are the priorities from either user happiness or revenue potential for us to focus on.

Delian Asparouhov:

Can you point to a particular example during your time at stripe where either the time at Dialpad or the International time at Google or maybe the early days of the SMB are held down even to customer operations, the very early days at Google? Can you point to a particular example where you were able to lean upon, let's say, prior experience, whether it's dealing with sales in APAC and knowing that people got to be up at 4:30 in the morning or how to think about CAC-LTV in the world of SaaS that applies to Stripe in some ways is a little bit of a confusing revenue model and that it's transactional, but it's always it has some similarities to SaaS? You have that upfront, it takes a while to pay back, there's generally a lot of expansion and sometimes crazy amounts of expansion, right?

Delian Asparouhov:

Lyft is a very large customer for Stripe, but maybe people didn't expect that when they first signed Lyft. We'd love to hear if there's a particular moment or set of lessons that you feel like really translated to Stripe.

Jeanne Dewitt Grosser:

Tons. A huge hallmark of my early career at Google was on Gmail, working really closely with the Gmail engineering team. I think that experience taught me about how to interact effectively and speak a language that the engineering organization finds compelling. Honestly, working for Google, which was very much in those early years, an engineering-led company and Stripe is too and there's a certain way to work and I picked those companies on purpose, but there is a certain way to work in those types of organizations that are engineering-led which I definitely learned at Google.

Jeanne Dewitt Grosser:

I would say like what coming in and the things I did around the operating model and a lot of the unit economics really actually stemmed also from my experience at Google where basically at the time, what happened at Google was, and actually frankly, my approach to enterprise really also stemmed from working at Google, so what happened was Google launched the G Suite product and they had these two early wins out of the gate, Genentech and Jaguar, the car company. They thought, "Oh, my God, we've got an enterprise product," and they started building out this massive enterprise team. They had a year where they hired like 100 midmarket reps and we really didn't. We basically got two visionaries.

Jeanne Dewitt Grosser:

The whole organization was oriented around enterprise, enterprise. It wasn't actually until the finance organization went out and did the analysis to understand our unit economics that they realized we are sitting on a goldmine in SMB and we should be flipflopping our investment and really going there. Meanwhile, our unit economics don't make any sense in the midmarket and enterprise and we actually need to pull back, retrench, figure that out before we can reinvest. When I came to Stripe, I didn't want to make that mistake which was not really understanding where your money was coming from and similarly didn't want to make the mistake because really where we got serious about enterprise was in 2017 when we won a deal with Amazon.

Jeanne Dewitt Grosser:

When you can get Amazon to sign your contract and then put material volume on you, you're like, "Oh, my God, we've got enterprise, right?" I didn't want to make that same mistake of being like, "Enterprise has arrived," when probably we had a visionary. Tons of learnings along the way.

Delian Asparouhov:

You started off essentially in an interesting role where you originally at Google were in the sort of customer operations role and then over the course of a very storied time, but relatively short period of time, now gone over the past 15 years from that role to leading a very large sales organization, one of the most promising startups in Silicon Valley. If you were to give advice to a recent, let's say, a Duke grad that was also trying to get into the world of startups, what would be your condensed version of the career decisions to make and high level strategies and frameworks around how to get to a position like yours, a bunch [inaudible 00:41:57] next 15 years of their career?

Jeanne Dewitt Grosser:

I think I'd have probably three main pieces of advice. The first one is work harder than everybody else. I literally would. I told the story to a couple people, but when I joined Gmail, we didn't employ enough people to answer these support tickets, so we had a two week backlog at one point and I just found that personally offensive that we're just doing so poorly. I came to the office, and mind you, came to the office because you couldn't take your laptop at home and work on VPN at the time, on a Saturday and worked from 8:00 AM until 2:00 AM on a Saturday to clear our backlog. I did that all the time. You don't get ahead by doing what everybody else is doing. You actually have to do more than what everybody else is doing if you want to get ahead of people. One is work hard.

Jeanne Dewitt Grosser:

Two, I would say is, don't let your job description define your job. At the time, here, I am this junior support rep and I basically ended up being like a real asset to the product management and engineering organizations because I would just go and show up at their meetings. I literally ... This is a fun example. We had a massive Gmail outage and they were doing a postmortem. Only engineers and our SREs were invited to this meeting and I [inaudible 00:43:36] them and I just showed up at their meeting because I was like, "We should probably talk about the user impact of this meeting and what can we do next time so that Gmail users aren't so unhappy when we have an outage because I bet this is going to happen again."

Jeanne Dewitt Grosser:

I wasn't invited. When I showed up in the room, no one knew who I was. 20 minutes in, I raised my little hand and was like, "I'd like to talk about what happened from a user perspective," and then that became part of our standard postmortem approach. I always think about your job expansively. Then lastly, work for a great leader. I have consistently throughout my career been, one, lucky to work for excellent leaders, and then two, once I realized that that was important, have actively sought out working for incredible people who I can learn from and who will take risks on me and sponsor my career.

Delian Asparouhov:

Those analogies all make a ton of sense to me, especially as somebody who really enjoys the ethos of working hard as controversial sometimes that can be in Silicon Valley today and learning from really smart people. I feel very lucky to have gotten to learn from very smart people including our dear friend Eric Lasker, who says, "You're welcome for dinner anytime you come down to visit the Varda office. We're happy to show you around the Space Factory factory, but thanks so much for taking the time to be on the podcast today, Jeanne. Really appreciated the conversation.

Jeanne Dewitt Grosser:

Likewise. Thanks a lot for having me and look forward to all sorts of conversations in the future.

Delian Asparouhov:

Thanks for listening, everyone. If you'd like to support the podcast, please sign up for a paid Substack subscription which we use to pay for transcripts, mics and other improvements. If you have any comments or feedback on what kinds of questions I should ask, who should come on the show or anything else, please do let me know. Have a great rest of your day.