Jun 20, 2023 · 45m · saastr
Scaling to $100M ARR: The Top 10 Mistakes to Avoid From LaunchDarkly Co-Founder Edith Harbaugh
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gold bands on the timeline = statements, start to end. Hover to read, click to jump. CC turns on captions
LaunchDarkly co-founder Edith Harbaugh shares key scaling lessons, strategic frameworks, and common mistakes encountered while growing a B2B SaaS startup from $1 million to over $100 million in ARR. Through candid reflections on talent acquisition, category creation, enterprise pricing, and intentional culture management, she provides founders with an actionable blueprint for navigating rapid expansion.
How this conversation actually went
Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. Jason holds 5.8% of the talking time here. How this is scored →
Jason as informed peer 0.6 Guest teaching 0.4 Guest disagreement 0.1 Jason pushing back 0.4
speaking balance: gold is Jason, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 37:34 Edith rejects 80-hour workweeks as counterproductive
Edith forcefully dismisses the hustle culture premise that working extreme hours produces superior results, noting it leads to snippy colleagues and severe mistakes.
Hardest push from Jason ▶ 43:53 Jason presses on technical competence in enterprise salesJason refuses a superficial answer, challenging Edith on how early non-technical reps can realistically close technical executives who have an allergic reaction to ignorance.
Biggest teaching moment ▶ 40:47 Edith dismantles the self-serve PLG assumptionEdith educates the audience on why self-serve PLG failed early on, explaining that enterprise buyers require personal trust and human touch before putting software into production.
Jason holds their own ▶ 40:19 Jason critiques founders treating PLG as a magical cheat codeJason demonstrates domain expertise by highlighting how founders mistakenly turn to PLG as an easy alternative once enterprise sales become expensive.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Jason as informed peer | Guest teaching | Guest disagreement | Jason pushing back | Why |
|---|---|---|---|---|---|---|
| Overcoming Persona Mismatch in Early Sales Leadership | 0 | 0 | 0 | 0 | Solo presentation segment where Edith shares the story of her first VP of Sales quitting over selling to developers. Since this is a keynote monologue, host-side metrics are zero. | |
| Navigating Fast Growth, Turnover, and Cultivating Culture | 0 | 0 | 0 | 0 | Edith delivers a solo keynote section discussing rapid scaling, turnover concerns from VCs, and instituting culture surveys and skip-levels. | |
| Revenue as Funding and Pitch Meeting Preparation | 0 | 0 | 0 | 0 | Keynote monologue covering revenue as self-reliance, citing Jason Lemkin's talk, and recounting an underprepared VC partner pitch. | |
| Matching Stage Expectations and Managing Executive Recruiters | 0 | 0 | 0 | 0 | Monologue advising founders on hiring stage-appropriate personnel and managing executive recruiters. | |
| Founder Leverage and Delegating Core Responsibilities | 0 | 0 | 0 | 0 | Edith explains founder leverage, delegating financial models and scheduling, and early enterprise pricing mistakes in a keynote address. | |
| Creating the Feature Management Category | 0 | 0 | 0 | 0 | Monologue detailing how LaunchDarkly coined the term 'feature management' to avoid being dismissed as just a boolean toggle or direct Optimizely competitor. | |
| Evolving Company Values and Culture Sustainability | 0 | 0 | 0 | 0 | Keynote monologue recounting how the original value 'work is not life' was weaponized by employees and eventually overhauled. | |
| Tailoring Playbooks and Summarizing Key Scaling Lessons | 0 | 0 | 0 | 0 | Edith concludes her presentation by explaining that founders must assemble their own play pages rather than copy standard playbooks. | |
| Audience Q&A: Executive Hiring, Value Rollout, and Category Creation Content | 0 | 0 | 0 | 0 | Audience members ask tactical questions regarding executive recruiting, value rollouts, and technical category marketing. | |
| Audience and Moderator Q&A: Growth Stages, Work Balance, and PLG Realities | 6 | 4 | 1 | 4 | Host Jason Lemkin steps in with sharp questions regarding founder work-hour polarities, the myth of PLG as a cheat code, and selling to intolerant technical executives. |
Statements from this episode (18)
LaunchDarkly has scaled to over $100M ARR since its 2014 founding
“Ah, so the company started in 2014 and is now over a hundred million in ARR.”
LaunchDarkly took two years to grow from $0 to $1M ARR
“So, 2014 to 20 16 was this very slow grind from zero to a million in ARR.”
Harbaugh: Do not hire sales leaders on pedigree without customer persona fit
“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.”
Harbaugh: VCs track startup turnover by analyzing LinkedIn departures
“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.”
Harbaugh: Unmonitored startup culture quickly runs away from founders
“If you don't pay attention to culture, culture will run away from you.”
Harbaugh: Informal 'no-deck' VC chats are evaluated as high-stakes pitches
“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, okay, 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 l…”
Harbaugh: $1M ARR hires build systems while $50M ARR hires operate them
“Every single one of these phases of one, five, 10, 20, and fifty million, you're probably going to be hiring completely different people. The people you're hiring at one million are the people that want to build the machine. The people you're going to hire at …”
Harbaugh: LaunchDarkly had no full-time finance hire until Series B
“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.”
Harbaugh: Early LaunchDarkly customers completely rejected self-serve credit card signups
“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 agr…”
Harbaugh: Enterprise software must price high because procurement expects 10% discounts
“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. Ah, and the insidious thing is that they also expect it to go to procurement and…”
Harbaugh: Low initial SaaS pricing anchors customers for life against upgrading
“What happens if you have a customer that is paying you 29, 79 dollars a month, is that you have anchored them for life, that this is a product that is worth 79 dollars a month. So, no matter how much you have other customers who are now paying a lot more and g…”
Harbaugh: Early Head-to-Head Sales Cycles Against Optimizely Totally Flopped
“Whenever we started trying to compete head to head with Optimizely, it just totally flopped. They had a nice WYSIWYG interface, and they sold to marketers. We sold to developers. But if we got in a sales cycle against them, it just completely disintegrated.”
Harbaugh: LaunchDarkly's 'work is not life' value was weaponized against deadlines
“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.”
Harbaugh: 500+ person companies need outside consultants to refresh company values
“When you're eight people, you can do a survey of your company very quickly. Ah, when you're 500 plus worldwide, you actually want a consultant who can come in and interview people, run focus groups, and get real input.”
Harbaugh: Early startups should hire number-twos before they become the perfect person
“So what you can do is you can look for somebody who's maybe the number two 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 t…”
Harbaugh: Constantly repeating company values reveals what is clunky and failing
“So, when you repeat your values over and over and over again, you learn what's clunky, what, what's not working.”
Harbaugh: LaunchDarkly required engineers to write an article every sprint
“Our engineers, at one point, we assigned them an article in every sprint, Ah, 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 data database migration is still a reall…”
Harbaugh: High ACV SaaS cannot rely purely on product-led growth
“The belief that SaaS is cheap and cheerful and something that's 29 dollars a credit card is being challenged, that now, like, 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 co…”