Scaling to $100M ARR: The Top 10 Mistakes to Avoid From LaunchDarkly Co-Founder Edith Harbaugh

Uh, so I'm here today at Saastr Europa to talk about top 10 mistakes getting $100 million. And my qualifications for this is, uh, I started off in engineering, I was product, I was marketing, I was sales and support, and then I was a founding CEO at LaunchDarkly. So the company started in 2014 and is now over $100 million in ARR. My joke is that I've always kind of started off in engineering and then worked my way out to the outer rim of the company. So my new role now is executive chair, which is super fun, but I'm going to tell you some lessons learned from when I was CEO. So LaunchDarkly, if you haven't heard of it, is a feature management platform. We have over 4,000 customers worldwide, and nothing makes me happier than when I go to a conference or event and somebody says that they use LaunchDarkly, you know, I started it because it was something I was really passionate about as a software engineer and product. It helps our customers release new features, migrate safely, target features, use experiment, and also do quicker mobile releases. So if you're a customer, thank you. And if you're not, give it a whirl. And that's all that Jason will allow me to say on that. So thank you. So $100 million does not happen overnight. Uh, so my job as a founding CEO was number one, to always make sure there was enough money for the company, to set the vision for the company, and then to drive forward. And these sound really simple, but it wasn't. Uh, so 2014 to 2016 was this very slow grind from zero to a million in ARR. The literal quote when I went to pitch Josh Stein, who ended up doing our A, was, "Wow, you guys really ground it out, huh?" You know, 'cause he's looking at, you know, our first month of selling, we had one customer. Our second month, we had one more customer. So if you're accruing customers at that rate, it's a long grind. But then things started going faster. So the period I'm gonna cover today is from 1 to 100. I think there's a whole nother talk I would love to give on the 0 to 1. Um, but that's a different phase. So my hope with the talk today is that you learn something. Uh, I hope you laugh at a couple of my jokes. Uh, I hope you laugh at me and the mistakes I've made. And I hope that if you're a founder or working at a startup, that it gives you some recognition of here's some pitfalls along the way, uh, either ones that you might be about to make or ones that you've already made and realize that you were not alone. All right, so with that, I'm going to start through the 10 things that were maybe mistakes. The first sounds really obvious, but if you're not making mistakes, you're not in a startup. If you're just doing the status quo and doing the things that always work, you would still be at a big company. You'd be at Microsoft. And I learned this phrase, everything is up and to the right if you zoom out. Went after our Series A, things didn't go so well. So we were an 8-person seed company with really tight rhythm, and we got our Series A, we hired our first VP of sales, and he was this great guy, wonderful pedigree, had worked at some, you know, really hot startups, and he said he really wanted to join LaunchDarkly. And, you know, I was like, wow, this guy has amazing pedigree, really passionate about customers, great references, He joined as our first VP of Sales. The issue was about after 3 months, he came to me and he said, "Edith, our customers are developers." I said, "Yeah, developers. Yeah, developers love LaunchDarkly. I love developers." He said, "Developers are a real pain to sell to." I'm like, "What?" He's like, "Well, they're very technical. They don't really like PowerPoint." They're very exacting, and they want the thing, they want a lot of proof points. I'm like, these are my people. I'm an engineer. And he's like, I don't like selling to developers. And he quit. Great guy, by the way. He went on to start his own company, which I actually angel invested in. So nothing to do with him, but more just there's this persona mismatch of he didn't like selling to developers, and developers were our core audience. And there was nothing you could do to fix that. So I had to very sheepishly kind of go to my new board member and say, hey, you know, all our forecasts for the year, when we said we were going to go from $1 to $5 million, we're going to be lucky if we eke out like $1.5 million, you know, because I got to rebuild the sales team. And I was extremely nervous when I went to tell you this. And what Josh said was the perfect thing to me, which was everything is up and to the right if you zoom out. 'cause I said, "You know, we're not gonna be up to the right for a couple quarters 'cause I have to rebuild." And he was totally right. We rebuilt the sales team. It turned out that the salespeople we'd hired were great, and they started closing big deals. And, you know, one of them, and then both of them actually entered the million-dollar-a-year club, which was pretty fun. So the mistake I made was, A little bit, I think, just being blinded by this guy with a great pedigree without really digging into whether he really cared about our customers. On the other hand, though, one of the salespeople that we hired at the time had never sold to developers before. He'd been a Twitter ad salesperson, and he turned out to be an amazing salesperson because he just had so much empathy for our customers, and he never talked down to them. They loved him. Like, I went on a sales trip with him once, and I'd never seen this before. The customer gave him a present. I was like, what? Yeah, he's been such a great salesperson. Cool. All right. I alluded to this before, but if you're a fast-growing company, there are big changes every year. So if you're growing from $1 to $100 million, that means you're basically doubling and tripling in size every single year. And a lot of people are really uncomfortable with that. What I always tried to do was to persuade people that, like, hey, this is a fun adventure, and you're going to have fun, but it's going to be different. A screw-up I did in the early days, again, from the transition from seed to A, was after we closed our A round, we started hiring a lot more people. And also, some of the people who had been there from the seed days didn't really like the new company, because they said, like, a 25-person company is actually a lot different than 8. Which is true. So we had a fair amount of turnover. I saw this as just kind of normal turnover and wasn't really concerned until we were trying to get our B together. And I got this frantic phone call of, why is your turnover so high? And I'm like, what? Turnover? What? And they're like, what about this person, this person, this person? And every single person, I had a really good justification of why it looked like that. So what VCs do is they'll have some poor associate look at your LinkedIn and look at people who have titles for companies who are going in and out. And what had happened was we'd had some contractors who we replaced with full-time. We'd had a summer intern who was never meant to be permanent. And then we had a couple people who were a little bit of a mishire. But when a VC looked at this, they're like, what the hell is happening with your turnover? So a change that I made immediately was to pay a lot more attention to culture. We started doing culture amp surveys just to get a pulse, and I also started doing a lot more skip levels with the team. Skip levels is when you meet regularly with somebody to kind of say, hey, what's up? And I think this really helped our culture become a lot stronger, and in fact, so that people started commenting about how strong the culture was. But it was definitely a wake-up call for me about if you don't pay attention to culture, culture will run away from you. Revenue is funding. So everybody here, I think, is in some sort of startup. If you didn't see Jason's talk yesterday, it was very eye-opening. He basically talked about the compression in valuations, that it's harder and harder to raise money, and that you have to have more revenue. I think this is always good to have revenue, because VCs can be a little fickle in terms of what they fund, but if you have revenue, you have a lot more leeway about when you take in investment. And also, by the way, the VCs like that because that way they know that you're a growing concern. So I always try to pursue this path if we had revenue. This really helped me a couple times when I completely screwed up the VC pitch. So a mistake I made was VCs like to talk to you. That's not the mistake. And they'll try to lure you in, and they'll try to extract more and more information from you. Again, in the A to B time frame, we were getting a lot of hits from VCs who want to learn more about the company. And they said, you know, come in. You don't have to have a deck. Just come in and talk to the partners. And I was like, OK, sure. And this was a huge mistake. I went into this, what turned out to be a partner meeting, and I was completely unprepared. I had looked at it as kind of like a workshop of I have some rough slides, they'll give me some feedback. They were looking at it as a pitch meeting, where they expected me to be on, polished, convincing, compelling. I was not. I had some rough drafts of slides. I was like, what do you think about this? They're like, eh. So the other funny thing, and I'll just briefly tell this story, is at the time I was back in DC to visit one of our— Washington, DC to visit one of our big customers. And for whatever reason, my iPhone at the time had wiped out all my contacts. It was this bad iOS release. So I had no idea when somebody called me who they were, which was kind of terrifying. You know, it was like, is it a customer? Is it a friend? Is it a VC? Is it a random number? So this number calls me and I pick it up and they're like, hey, and I'm like, hey. And they're like, how's it going? I'm like, it's going good. Me, I'm trying to figure out, is this somebody trying to sell me car insurance or what? And I'm like, I'm in DC visiting a customer. And they're like, oh yeah, customers are great. And then it turned out to be the VC that I had gone into the bad pitch meeting with, and he was calling to tell me that they weren't going to fund me. Fund. This was not great for me because I was not prepared for this call. And, uh, I got off the phone, I was like, I'm gonna do 10 times better in the next pitch. So every time I went into a pitch meeting after that, I was as prepared as I could be. You know, even if I didn't need to have a deck, I would have a deck ready, I would have my pitch ready, I would have numbers ready. And I never took it for granted again that these were automatic yeses. Uh, always be prepared and also always have the backup plan of revenue. Uh, every time, uh, I got a little bit nervous about VC funding, I would try to close more deals. Worked out. All right, I alluded to this before when I talked about changes. Every single one of these phases of $1, $5, $10, $20, and $50 million you're probably going to be hiring completely different people. The people you're hiring at $1 million are the people that want to build the machine. The people you're going to hire at $50 million are the people who want some sort of machine that's already running. So really be careful about when you interview people about what they actually want. Startup gets thrown around a lot, and startup changes every single phase. So you might get somebody who thinks that they want to work at a startup, but what they really want to work at is Google. You know, they're like, "Oh, a startup, Google, they have free massages and free bikes, awesome." You're like, "No, actually we're 15 people and the refrigerator makes a ton of noise." So be careful about who you're hiring, be careful about their expectations, and be careful about the infrastructure that they expect. Again, we had people who came in and they just expected a lot. And we're like, no, we want you to build that. We don't have that yet. Which gets me kind of to executive recruiting. How many people here use an executive recruiter? All right. So, let me briefly explain what a good executive recruiter does. A good executive recruiter, I call it like kind of like a real estate agent or a matchmaker. Say you're in the market for a new CMO. If you just put up a listing that says you're looking for a CMO, it's probably not going to get a ton of traction. You're either going to get a lot of random resumes or people who are just not really a good fit. So a good exec recruiter knows who's in the market, knows who's available, knows who maybe doesn't really want to advertise that they're available, but is looking for a job. So the most recent search we did actually this way was a GC, a general counsel, and that was a really good fit because they got what LaunchDarkly did and could find a great candidate. However, a bad executive recruiter can really torpedo you. We had one executive recruiter who got this great candidate, and I found out later that the candidate almost didn't join the company because of the high-pressure tactics the recruiter used. You know, the executive recruiter gets paid when a candidate signs, so their motivations are a little bit different than yours. Like, so the executive recruiter was telling the candidate they had to sign within 24 hours or I would pull the offer. I was like, no. I mean, it's not open for 3 weeks, but if you need to go talk to your partner, spend some time thinking about it, of course it's open. So make sure that your executive recruiters align with you on how they close candidates. Another issue you could have with exec recruiters is just them trying to, again, jam somebody in. A real issue is if they, like say you have budgeted £150,000 for a role, and you're like, this is about what we think the market is, and then they keep bringing you candidates that are $250,000, and it's just not gonna work. You gotta have alignment. So a good executive recruiter is totally worth it. A bad one is not. The main reason an executive recruiter is totally worth it is 'cause you need to fill that role, which brings me to the next one. Get leverage. I was guilty of, holding onto stuff way too long so many times. So, we did not have a full-time finance person until our B round. So, up until our B round, I was still running all the models and the spreadsheets. In my mind, this was not a huge overhead. Like, I like Excel, I like numbers, I'm a nerd. It was taking me like a couple hours a week to keep running the models, and I didn't see this as a huge overhead. In hindsight, it was a big drag on the org. Those 2 hours that I was doing these spreadsheets was 2 hours that I could have been doing something else, and there's a lot of other things that a full-time finance person could be doing that I just had no room to squeeze in at all. So as soon as you start growing, look at what you're spending time on and see if you're really the best person to keep doing it. Again, something I was guilty of was I didn't have an EA until pretty late, an executive assistant. In my mind, it's like, well, it's not that much time for me to schedule these meetings, you know, I'll just fit it in. Finally, what happened was our then VP of sales said, "Edith, I want you on the phone with customers, not trying to schedule your own darn meetings." That was a wake-up call to me. I saw it as, hey, I can just get everything done because I'm Superwoman, not, hey, even Superwoman needs to narrow her scope a little bit so that she can be more successful at that. So my advice to everybody is, as soon as you start progressing, try to get leverage wherever you can in your own tasks, and don't hang on to stuff for too late. All right, pricing. Uh, it's funny. So, uh, pricing is one of those things that can be a total time suck because there is no right answer of it. Uh, one of the issues we had at LaunchDarkly was we sell both to B2B and B2C. So these are totally different markets sometimes with different mental models. And we also had this kind of existential talk about are we B2B or B2C? What happened was our first attempt at pricing was we tried to go cheap and cheerful. We had a click-through where you could go and sign up with a credit card. Easy peasy. Don't need salespeople. What happened for us is that absolutely nobody wanted to use our click-through agreement. Everybody wanted to talk to a salesperson. Everybody wanted some sort of custom contract. And I was a little annoyed by this, to be honest. I was like, you know, kind of like, please just use our nice credit card thing. And what I did to try to dissuade people from wanting custom contracts was I said, well, if you want a custom contract, we're going to charge you a lot more, thinking that this would scare people off. People are like, great, custom contract us. I was like, shoot. And that was when I started using my infamous phrase that the engineers tease me about, which was, I should have asked for more money. If you're in an enterprise sales cycle, people expect you to ask for money. People are paying for a premium service. They're paying for a premium ELA. They expect it to be higher. And the insidious thing is that they also expect it to go to procurement and get knocked down by 10%. So if you don't ask for more money out of the gate, you're actually kind of misselling yourself. So underpricing can be as bad as overpricing in my mind, because it also then pigeonholes you. So in the early days, I did all the sales, and I didn't really know what the product was worth at the time. I also was really shy. I was a very shy engineer. So I would ask for $29 or $9 or $2 if you could afford it. So we literally had some contracts on the books that were for $9 a month. And the idea was that over time, these customers would hopefully start upgrading and pay us more money. What happens if you have a customer that is paying you $29.79 a month is that you have anchored them for life that this is a product that is worth $79 a month. So no matter how much you have other customers who are now paying a lot more and getting true perceived value out of it, if you have $79 a month customers, they don't want to move up at all. And they have a budget for that, and that's what they want to pay. So there's no right answer. I just encourage you all at your own startups to think about what value are you providing to customers? What is our perceived value for that? And if you have any hopes that people will automatically start paying you more money, it's very rare. People will pay what they anchor at. Always keep creating category. So when LaunchDarkly started in 2014, there was no such thing as feature management. How do I know that? Because I made up the word feature management. I made it up because I'd had this background in portal management and content management, and I'm not very creative a person. So I was like, what do we do? We manage features. Feature management. The reason why I wanted to be called feature management is at the time people were doing feature flagging, feature toggles, and these made it sound like a toy. Like if you say, I'm going to pay money for feature toggles, people are like, well, that's just a Boolean. You know, that was literally the quote that we got in Hacker News. Why would anybody pay anything for Boolean? So we were trying to uplevel and move it to feature management. The other reason why we wanted to be feature management is back then, this was a very different world. People were trying to compare us with Optimizely, which was a pretty entrenched company at that point. Optimizely, for those who didn't know, had come out of Y Combinator. Their sell was that you could do on-the-fly experimentation, A/B testing. So whenever we started trying to compete head-to-head with Optimizely, it just totally flopped. They had a nice whizzywig interface and they sold to marketers. We sold to developers, but if we got in a sales cycle against them, it just completely disintegrated. The other thing we found was that people were experimenting a lot less than everybody thought. So my own background had been, I'd been at TripIt where I had experimented heavily. My co-founder had been at Atlassian and he'd also experimented. What we found when we got out into the real world and were trying to sell in 2014 and 2015 was that people really weren't experimenting as much as we'd hoped and they were just struggling with big releases. So we did this big pivot, uh, into feature management. What we found now in 2023 is that finally there is enough, uh, momentum in the market that experimentation is viable. Uh, people who have reliable releases are able to do experimentation. So we were able to keep creating a category, but we had to get some beachheads in first. Refreshing values. How many people here have written down values? Awesome. So one of the things we did when we moved from a seed company to an A company is we actually wrote down our values. When you're 8 people, you just kind of know your values. You all eat lunch together every day. You know what's happening. When we got our A round, we knew that we were going to hire more people, and we decided to write down our values. So my co-founder and I did a survey of the 8 of us and asked what our values were. And from that, we kind of distilled it down, and we thought we did a pretty good job. So there were things like learn and grow, which was a big one for me. If you're not making mistakes, you're not learning. Respect for each other, our customers, our community. But then you can kind of see when we ran an oof when we were doing our values, because we had this last one, which was work is not life. And our literal thought at the time was, this is a little clunky, but we have other things to do right now. We'll just leave this be. And over time, over the next 3 to 5 years, this value work is not life became a little problematic, in that what our intent had been was, We want to have a company where you're not working 80 hours a week. We want to have a company where you have a sustainable pace, where you can have kids. My co-founder had another kid, our engineer had 2 more kids. We wanted to be a place where you could have a life, but still get stuff done. What happened with this work is not life value was that people started weaponizing it of, we don't have deadlines. I don't owe my other teams anything, or I don't really have to work very hard at all. I was like, no, this is not Tim Ferriss' 4-Hour Workweek. We owe our customers. We owe other teams. We got to do more work, but in a sustainable way. So I actually, after 5 years, I decided that one of our actual annual objectives was going to be to refresh our values. And this time we hired a consultant, and that was great. Again, this is the way to get leverage. When you're 8 people, you can do a survey of your company very quickly. When you're 500+ worldwide, you actually want a consultant who could come in and interview people, run focus groups, and get real input. One of the most interesting things was when we did this survey, about 90% of the company loved our old values. They didn't want to change. I was the one that wanted them to change. I wanted them to reflect the company that we were. So we did this big project, and we changed the value of work is not life to work impactfully, work sustainably. And I think it was a big success. But don't be afraid to change values. And also, like I said, the mistake I made was, I don't know if it was a mistake. It was just having a value that wasn't quite right, and the longer that time went by, It just kind of didn't sit right more and more and more. All right. So I talked a lot about culture, about making money, about building a company and scaling. I really want to reinforce that there's no right playbook, just play pages. A lot of the tactics that worked in 2015, 2016, 2017, might not work now, but on the other hand, tactics that didn't work in the past can work now. So, a real example from LaunchDarkly is in the early days, we were experimenting with cold outbound emails, you know, traditional BDR activities. We had these nicely written emails and they went out, and the issue was absolutely nobody understood what feature management was at all. So, just nothing resonated. We finally just terminated the campaign because, I was, I at the time was being the AE, and I would just take a lot of calls from people that wanted to have an agile consultant. I'm like, no, that's, that's not actually what we do. The one success we did have out of it was we sent a cold email to somebody at Microsoft, and he said, this is the greatest thing I've ever heard of. Can you build a connector to Visual Studio, and can you come talk at Microsoft Build? And I said, "Yes." The other thing he said is, "We really want to show that we're startup-friendly. Can you get a booth at Microsoft Build?" And at the time, our marketing budget per year was $36,000. A booth was about $40,000. So I said, "Well, that's kind of outside of our budget." He said, "We'll give you the booth for free." So from that one cold email, we got a wonderful relationship with Microsoft, and a free booth. Their signage was very nice. So, this was a play that we ran that had a very limited result, but worked out. And then, 3 years later, we could ramp up and have an actual BDR team and reach out to customers, because people had— knew more what we are, and we had more space in the market. So, I really encourage everybody, if you're interviewing or thinking about your company, It's tempting to say, you know, I want to run the Box playbook, you know, or I want to run the LaunchDarkly playbook, or I know that Dale spoke earlier today, I want to run the Dale playbook. The right playbook is a bunch of pages that you're tearing out of other startups about like, what should my pricing be? What should my culture be like? What market should I go after? And you got to reassemble them for something that works for you. With that, Here's a wrap-up slide. I'm just going to quickly run through it. Path to $100 million. There was a lot of, if you look at it, a lot of dip, then it went up. Be ready for big changes. I cannot emphasize this one enough. Revenue is its own funding. It's easy to get wrapped around the axle of what do VCs care about. VCs care about companies that make money. If you make money, VCs will care about you. Hiring changes over time. Value your time and get leverage. Executive recruiters, worth it. No right answer for pricing. Always be creating a category. If you were noticing carefully, I tried to weave LaunchDarkly into at least 4 different slides. Always, always, always talk about your company. Refresh your values if you need to, and again, Startups are fun. You're going to make mistakes, but please take some pages and have fun with it. With that, I'm going to turn it over to Q&A.

Hello. My question is about hiring. So first of all, you want to hire people who already done something that we want to achieve, but at the same time, if they already done this, why they should be joining you? So for example, let's say you want to hire like head of marketing, but if they are already a great head of marketing, most likely they will be interested in moving to the VP marketing, CMO role in the bigger companies, no?

Yeah, that's a great question. So let me paraphrase it. How do you get people to join your company who have done it? And it's funny, this was a constant thing with me and one member of our board. It's like, well, the person who's gone from 0 to 100 probably doesn't want to join at 1. They probably have a lot of opportunities. So what you could do is you can look for somebody who's maybe the number 2 at a role or an adjacent industry. The adjacent industry doesn't always work out. But you could get kind of somebody who's just that one step below. But it is hard because people have this vision of this perfect person. And you want that perfect person before they're the perfect person. And they become perfect while they're at your company. Good question.

Hello, Ida. Thank you for what you've created. It's helped us really accelerate our— product development process, and I like sneaking in myself and enabling some features for me to test. But my question for you is, the values that you talked about, and with changing them so regularly, are your values still, and your co-founders, still kind of aligned with the wider company values? Are they still in there, and how do you roll those values out with 500 people when you're refreshing them and making them real rather than just kind of an update on a wall somewhere?

Yeah, that's a great question. So we actually put a lot of effort into the values. So the original values, I actually did a session with all the new hires. So every 2 weeks to a month, I would do a session with everybody who joined. It was off the record. I said, don't tweet me, don't quote me, but you could ask me anything you want. And I would walk through the values and why they existed. And I love doing this. I thought that it really instilled with the team what the values were. And it actually, it was one of the reasons why I decided that some of our values were clunky. One of our other values at the time was teams, not fiefdoms. We're nerds. And I got tired of answering the question of what's a fiefdom. So when you repeat your values over and over and over again, learn what's clunky, what's not working. So, when we rolled out the new one, we actually had consultants who helped us. Like, we did a town hall, we did focus groups, we did a lot there, which I don't want to spend too much time on, but it was a deliberate effort of making sure they weren't just words on a wall. Even things like, hey, are they easy to remember? And do we have examples of them? I think you're next.

Thanks. Enjoyed that talk. So my company, Search Pilot, has the exact problem of the category creation that you're talking about. We're trying to do SEO A/B testing.

I'd love any tactical examples you have or things that worked or didn't work on the path to successfully creating the category that you've done.

Yeah, I mean, just everything. Data everything. The advantage we had was that we targeted developers. And what I learned was that there wasn't a lot of technical content out there about what we did. So, like, simple articles that I thought were kind of throwaway would get a ton of hits. You know, like, I wrote something like the top 10 ways you could feature flag, and that got some traction. I looked at what the number one hit for feature flags at the time was, and it was feature flags, the worst kind of technical debt. So I wrote a rejoinder called "Feature Flags Are the Best Kind of Technical Debt" and submitted it to QCon. I did a podcast. I think podcasts are a little oversaturated now, but at the time, it just wasn't much out there. Just constant, constant, constant, everything you can to get the word out. And then like our engineers at one point, We assigned them an article in every sprint. It was literally like, you know, part of your sprint is not just checking in code, but also writing about it. And one of those articles about database migration is still a really good article that 7 years later gets a lot of hits. I could talk about this for hours.

Appreciate it. Thank you.

So thank you for your great talk.

My question is also surrounding hiring. So you mentioned you hire different type of type of people at different stages of growth. And I was wondering what, from your experience, are the typical threats what you're looking for in a $20 million-plus ARR business?

Sorry, can you repeat that?

So a $20 million-plus ARR business, what are the specific types of people you're looking for at that stage from your experience?

Yeah, so one of the screening questions I would ask is, what's the smallest place you've worked at, and what do you like and not like? And that was pretty good at sussing out what people actually liked at different stages. At $20 million, you have at least basic processes. You have departments. You don't just have one team. You probably have functional leaders. So people who are comfortable with that. If they say, hey, I still want to be in a 10-person team, that's not going to work when you're at $20 million unless you're probably not in a SaaS business.

Thanks for that. And I'd like to understand if your, I guess, technical requirements for your salespeople changed over time as you grew.

Yeah, it's funny. So I referenced that, um, one of our most successful salespeople— and he's still with the company, by the way— does not have a technical background. Um, but what he did was he just was extremely willing to learn on the fly. And asked questions, and then he never talked down to customers. So he was always just very empathetic. You know, I can say this as an engineer, engineers could be kind of dismissive technically sometimes, and that's not a good look for a salesperson. You know, if a customer doesn't understand something, it's your job as a salesperson to educate them, not to lecture them.

Values with your co-founder on, um, sorry, help me, I, I'll misquote it, but, uh, work is not life.

Uh, how—

this is not one I struggle with all, or at least think about all the time. The world, you, you have to be more and more agile today, I think, in SaaS and software. We all know, like, there's so many competitors, things are faster. And what have you learned and balanced that on the way to 100? And I think the views have gotten even more polarizing, right? I meet more really young first-time founders now that literally are working 7 days a week and want the most intense cultures. And on the other hand, I think during lockdown a lot of folks worked even less. Maybe a lot of, a lot of folks started working 15, 20 hours a week. Um, so what have you learned on that journey to 100 and how to, how to make that work and but be competitive? Because you had to win in a competitive category.

Yeah, well, thank you, Jason M. Lemkin. So I think my intent was— so I'd been in startups since the dot-com era, and I'd been that person that worked, you know, 80, 90 hours a week. I remember sleeping under my desk because the BART had shut. And it's not sustainable. It leads to a lot of burnout. It leads to people just not doing their best work, is the other thing I learned that I was working more hours, and I would come back and look at my work the next day, and I had made so many mistakes. You know, I was in engineering at the time, and I did some work that ended up getting patented, which is great. So, clean technical writing was really key. And if I was like in this brain fog, I wasn't doing great work. And the other thing that would happen is if you get a bunch of snippy people who are working on little sleep, they start getting very snippy with each other. So it's not a productive environment. You think that you're working more, you're really getting less done. So what we were trying to build was this thing where you could do your best work. And definitely there were some weeks where we were working 80, 90 hours, but those were kind of these peaks and valleys of like, you know, I talked about how we did the Microsoft Build conference. You know, at the time we were an 8-person company, so all the engineers like came and ran booth with me. You know, and I could ask them to do that, because I'm like, hey, this is a one-time thing, you know, we're getting stuff off the ground, but if we'd done that every single week, like, I know how much work goes into a conference. And so you have to balance asking your team to go up there and then saying, like, hey, there's going to be this other week where it's going to be a little less hectic. Hi. Firstly, as a woman in tech, I have to say your story is really inspiring, being a technical founder and growing the company like you did. So thank you. Um, secondly, obviously following the 2021 Series D funding, when you think about the future growth and next stage of growth for your company, what are your thoughts, um, when it comes to thinking about a possible IPO in the future? Uh, I think it's just like everybody else. Uh, it's one path for the company, What I always told the company is it's just one step in a journey. You know, you can go up on stage and ring the bell, and then you still have to run a company and do a lot of work. So it's just a step in the journey. Where I've seen it backfire in companies is when they get too wrapped up in this one event, and then, like, you know, life continues after it. You still have customers.

But I think you hit on some interesting things of really going from a self-service PLG motion in the early days. And PLG, everyone wants to do PLG. They think it's a cheat code. Like there's so many folks that think, oh God, sales got so expensive. I've spent all the money in 2021. I'll magically turn on PLG, these three initials. It sounds like you really went the other way very early from customers. And what did you learn about some of the fallacies of PLG, fallacies of self-serve beyond just pricing? But that was very interesting as well.

I think at least in our early days, what I discovered was that people weren't buying a product so much as they were buying a belief that the company would help them. You know, so I remember I went to an early sales call at CircleCI, who was actually friends with us, and they asked me a couple questions. I answered. The CTO also answered. I was like, well, why did you need to do this? They're like, oh, we just wanted to know that we could trust you. So a lot of sales is trust. So the reason why PLG didn't work for us very much in the early days is we realized that we were a new category. SaaS was still a little risky. And people really needed to feel like they could trust us. I think— and I cribbed this from another talk, so I forget which one. Also, the belief that SaaS is cheap and cheerful and something that's $29 a credit card is being challenged, that now SaaS can go for hundreds of thousands of dollars. And at that point, a CFO does want to get involved. And that's not something that could be very PLG. You can run a— let me say there's this false economy. People still love to do trials. People like to see the software. People like to know that it works for them. So, like, the old enterprise scare tactics of you have to sign a contract to even install it don't work. But if people are going to go live in production, they do want to have some sort of sales motion to know that there's a company behind it, to know that there's something they can call when they need help. Cool.

And maybe one other interesting thing you said in the talk, if I get another one. You talked about the AE that had come from Twitter that was curious. And thoughtful and the customers liked. I was able to succeed without a technical background. But to take that, let's flip. How many folks in the early days of LaunchDarkly maybe faced how technical, and I'll put technical in air quotes, did the sales team need to be? A lot of folks struggle with this for B2D, how technical they need to be. And a lot of folks in vertical SaaS struggle on a variant of this, which is domain expertise, right? I'm selling a deep environmental compliance product. Do my reps need to know how this works? And it's, It's a very interesting question because I don't think the answers are obvious. So what did you learn about domain expertise being technical?

Um, so I, it's funny because I do have an engineering degree. My co-founder has a PhD in CS, so I would say we were both considered technical. But when we started hiring our first salespeople, I remember telling them that they were an expert in what LaunchDarkly did. They were trusted advisors and that nobody knew as much as they did about LaunchDarkly. And that really helped them with the boost of confidence of, hey, I'm here to help the customer. I don't have to understand everything about what they do, but I need to be able to understand how LaunchDarkly works with them. And that helps slot it in of, I'm not here to lecture, I'm here to help.

Got it. So you did all the first 20 sales executives on the team. Did they, did they need to be able to speak with enough confidence to a VP of Eng or CTO? How did they overcome that hurdle? Uh, I, from my perspective, I, I, I think about it more simply, which is most VPs of Eng and CTOs, they won't suffer fools. Like they smell a fool in the sales process and they just, they they have an allergic reaction to someone that doesn't under— but most sales reps cannot, they have to find a way to speak and work at that level without having that skillset. So how smart did those first 20 have to be or special?

So I am over time, but it's Jason's conference, so I'm gonna answer this one. It's a mix. I mean, the thing, this is about no right playbook, is LaunchDarkly was creating this field. So there weren't people out there that were experts in feature management. It was like we were creating feature management, so we had to train the salespeople in how do you talk about feature management. The first 20 came from a mix of different backgrounds. Some were from traditional, I'd say, BD companies like New Relic. Some we got from more apps, like from App Analytics. So they had to at least know the basics of what is an SDK and what does an engineer do? But the most important was really just, again, figuring out how to slot that into a customer's workflow. And as you said, VP engineering, they don't like fools. So being in a non-dismissive way where they can work together. I'm out of time. This was really fun. If you have more questions, I'm happy to talk more, especially if it's about Tactics for category creation, because I have like 10 more things I want to say now. Thanks.