Apr 14, 2024 · 1h 21m · lennys-podcast
The GitLab way: Kindness, transparency, and short toes | David DeSanto (CPO)
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GitLab Chief Product Officer David DeSanto joins Lenny Rachitsky to discuss how the world's largest all-remote company operates using radical transparency, asynchronous workflows, and unique cultural values like 'short toes.' He also shares insights into product management craft, transitioning from product breadth to depth, and deploying multi-model enterprise AI.
How this conversation actually went
Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. Lenny holds 24% of the talking time here. How this is scored →
Lenny as informed peer 3.4 Guest teaching 3.7 Guest disagreement 0.1 Lenny pushing back 1.1
speaking balance: gold is Lenny, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 21:12 Pushing back on transparency limits in SaaS
David directly rejects Lenny's proposition that radical transparency only suits open-source developer platforms, citing specific enterprise SaaS retention gains from public feature backlogs.
Hardest push from Lenny ▶ 1:13:11 Challenging GitLab's vague website messagingLenny candidly pushes back on David's platform summary by looking at the live website and pointing out that tagline slogans fail to communicate what GitLab actually does.
Biggest teaching moment ▶ 37:56 Reframing deliverables versus customer adoptionDavid educates Lenny on why measuring bug fixes or feature shipping counts fails in remote environments, teaching the importance of scoping work around customer adoption metrics instead.
Lenny holds their own ▶ 1:01:12 Synthesizing HubSpot and GitLab breadth strategiesLenny demonstrates deep product knowledge by comparing GitLab's multi-product rollout to HubSpot co-founder Dharmesh Shah's 'top three' anti-focus product strategy.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Lenny as informed peer | Guest teaching | Guest disagreement | Lenny pushing back | Why |
|---|---|---|---|---|---|---|
| Episode Highlights: Transparency, Short Toes, and Remote Work | 0 | 0 | 0 | 0 | Teaser clips and host introduction outlining GitLab's unique culture and David DeSanto's background. Lenny reads the episode overview as a monologue. | |
| Sponsor Break: Orb and Eppo | 0 | 0 | 0 | 0 | Sponsor reads for Orb and Eppo followed by lighthearted introductory banter between Lenny and David discussing David's signature beard and Threads handle. | |
| Extreme Transparency: Publishing Team Meetings on YouTube | 3 | 5 | 0 | 1 | Lenny asks about GitLab's practice of publishing internal meetings on YouTube. David explains the mechanics, policies, and surprising benefits of external open-source contributors fixing bugs seen in meetings. | |
| The Open-Source Handbook and Public Product Direction | 4 | 4 | 0 | 1 | Lenny notes specific sections of the GitLab public handbook like PM leveling competencies. David shares how startups and external companies frequently fork GitLab's handbook and follow their public issue trackers. | |
| Execution Over Secrecy and Shipping Cadence | 4 | 4 | 0 | 1 | Lenny observes that radical transparency proves execution matters far more than secret ideas. David agrees, sharing how CEO Sid Sijbrandij reframed ambitious roadmaps and highlighting their streak of 149 monthly releases. | |
| Operationalizing Transparency and Navigating Risk | 3 | 4 | 0 | 1 | Lenny inquires about the downsides and operational risks of extreme transparency. David details accidental public postings and gives tactical advice on easing an organization into internal transparency first. | |
| Business Benefits of Radical Openness and Async Alignment | 4 | 4 | 1 | 2 | Lenny presses on whether public transparency mostly benefits open-source developer platforms rather than traditional SaaS like Salesforce. David gently pushes back, arguing enterprise SaaS can drive customer retention and expansion by sharing roadmaps. | |
| GitLab Values: Kindness, Short Toes, and Intentional Collaboration | 4 | 4 | 0 | 1 | Lenny and David explore core cultural values like kindness, assuming positive intent, and having 'short toes.' Lenny highlights the contrast with Uber's famous toe-stepping culture. | |
| Long-Term Vision, All-Ops Strategy, and Team Empowerment | 3 | 5 | 0 | 1 | Lenny expresses surprise at GitLab's multi-decade mission and seven-year planning horizons. David educates him on how GitLab translates long-term vision into autonomous group-level execution and all-ops strategy. | |
| Why People Struggle in All-Remote Environments | 3 | 3 | 0 | 1 | Lenny asks why some new hires fail in an all-remote environment. David explains that the lack of spontaneous in-person contact and the unique lifestyle adjustments are usually the primary failure modes. | |
| Frameworks for Remote Success: Outcomes, Communication, and In-Person Gatherings | 4 | 5 | 0 | 2 | Lenny pushes David on the difficulty of measuring outcomes instead of hours in software engineering. David clarifies the distinction between shipping arbitrary deliverables versus driving customer adoption metrics. | |
| Sponsor Break: Paragon | 3 | 4 | 0 | 0 | After a sponsor break for Paragon, Lenny asks David for advice for people considering product management careers. David warns that good PMs frequently annoy cross-functional partners by pushing hard boundaries. | |
| Remote Product Execution and the Deep-Dive Interview | 4 | 5 | 0 | 1 | Lenny asks how remote PMs handle informal check-ins without hovering. David explains GitLab's rigorous deep-dive interview simulation and advises against waiting for weekly ceremonies to unblock developers. | |
| Internal Tooling and the Handbook-as-Code Operating Model | 4 | 5 | 0 | 1 | Lenny asks about internal tools and handbook governance. David details the handbook-as-code workflow, dogfooding GitLab issue trackers, and anti-email practices. | |
| Time Zones, Inclusion, and Global Asynchronous Work | 4 | 4 | 0 | 1 | Lenny asks how GitLab coordinates across global time zones without exhausting staff. David describes asynchronous DRI decision-making, optional recorded calls, and local leadership delegation. | |
| Product Strategy: Transitioning from Breadth to Depth | 6 | 4 | 0 | 2 | Lenny brings in an insider question from former growth head Hila Chu about breadth-over-depth product strategy and compares it to Dharmesh Shah's HubSpot approach. David explains the strategic pivot from wide wedge to deep moat in core categories. | |
| GitLab Duo: Principles and Multi-Model AI Strategy | 4 | 5 | 0 | 2 | Lenny asks about GitLab Duo and AI architecture, specifically probing if partnerships with Anthropic and Google are meant to avoid Microsoft and OpenAI. David explains their multi-model philosophy, strict IP privacy commitments, and speed requirements. | |
| Leadership Tactics: Using Humor to Navigate High Stakes | 4 | 3 | 0 | 2 | Lenny explores David's tactical use of humor in high-stakes executive negotiations and teases David about GitLab's overly generic marketing copy on their website. | |
| Lightning Round: Books, Tools, Interviewing, and Mottos | 3 | 3 | 0 | 0 | Lenny and David run through the lightning round covering Geoffrey Moore's frameworks, the STAR interviewing technique, favorite tools like Arc and Superhuman, and closing calls to action for the open-source community. |
Statements from this episode (26)
GitLab encourages employees to livestream internal team meetings to YouTube
“Our policy is like be as transparent as possible. So if it's not customer data, it's not vulnerability information. We heavily encourage the team to put their videos, like record their videos, sometimes even live stream them onto our YouTube channel.”
Open-source developers contribute code to GitLab after watching public meeting videos
“The great example I can give you is like, we get people who then contribute because of what they see. And so we've had, you know, customers, open source community members go, oh, I can go build that. I know what that is. And they will just Knock it out and do …”
Startups frequently fork GitLab's public handbook to build internal operating procedures
“We'll have companies who will fork the handbook cause it's just source available too. At the bottom of the page, you can click views, view source. And I just heard from a company who's now becoming a customer who were like, we wanted to redo our UX mission and…”
GitLab leaves the majority of its internal issue tracker publicly viewable
“So the first one is our issue tracker for everything we're doing. The majority of those issues are public. It's also available for people who have an account. To also create and comment on.”
DeSanto: Product teams set ambitious goals and engineering teams must meet them
“It's product's job to be ambitious and it's engineering's job to meet that ambition.”
GitLab has shipped 149 consecutive monthly product releases over 12 years
“We still ship 12 releases a year. It used to be on the 22nd of every month. It's now the third Thursday, so we don't have to have people work over a weekend. We've done that for over a decade and our last release put us at 149 releases that have come out essen…”
GitLab occasionally publishes confidential issues and internal recordings by accident
“GitLab has had its fair share of things at times where an issue is public that probably shouldn't have been public, like in our issue tracker, or, you know, the recording accidentally gets set to public when it should have been set to private.”
Transparency is easier than secrecy because tracking internal communication creates overhead
“It's actually a lot easier to be transparent than it is to not be transparent. Cause now you don't have to worry about tracking things you may or may not have said. Think about, well, did this person hear it or were they not in that meeting? Like it just becom…”
Publishing external feature requests increased customer retention and expansion revenue
“My last employer, we started sharing the list of open requests for new features more externally, and we got a much more honed in roadmap. And that led to better customer engagement, which led to a higher retention rate, which led to better expansion numbers, r…”
Restricting negative feedback to one-on-ones preserves trust in public company channels
“You don't want someone to take a public message the wrong way. And so you take that conscious step to say like, Hey, I gotta give that feedback. Let me do that one-on-one. And that means like, if it's in a public channel, it's even easier to assume the positiv…”
GitLab's 'short toes' value means separating work feedback from personal identity
“So the short toes is, you know, it's really about the, it's about the work. It's not about you. And so if you have made something and you're getting feedback on it, try to realize that is someone trying to help you make it better and not a personal view of how…”
GitLab's three-year product strategy is to become the first All-Ops platform
“The three-year strategy says our goal is to become the first all ops platform. And that is essentially to say that we want to be the single source of truth for R&D organizations.”
GitLab currently maintains approximately 72,000 open issues in its public backlog
“We have, I think, 72,000 open issues right now in our backlog”
High-performing GitLab employees primarily churn because they miss daily office interaction
“So I think it really kind of dives into the remote experience. Remote is not for everyone. And we'll have people who come and they're really great. They don't even have to be an under performer, but they're missing that in office every day feeling. Maybe some,…”
GitLab was the largest all-remote company before the pandemic with 1,100 employees
“We were pre the pandemic when we were around 1100 people.”
Remote leaders must aim for 150% communication clarity to achieve basic comprehension
“One thing he said was that, you know, if you think you're communicating a hundred percent accurately, that's probably a 60 or 70% for the other person and shoot for like a 150%. And so that's something that I think really helps in that environment.”
Product managers are likely succeeding if cross-functional stakeholders are annoyed
“You know, the way I tell people who are new in their career, maybe they're now an associate or intermediate PM at lab or other places I've worked that like, if everyone's really annoyed at you, you're probably actually doing your job well.”
Remote product managers must refine requirements upfront instead of relying on standups
“If you're in an all remote world, your requirements have to be clear. You know, sometimes you can get away with, Hey, this, I have a daily stand up or a couple of weeks stand up. And then you use that as the opportunity to clarify something. You have to get it…”
GitLab tests PM candidates using an asynchronous written requirements roleplay simulation
“And so as part of the interview process at GitLab, we do what's called a deep dive interview, where we have the person try that out and they engage with another person or product who's playing the engineering side of that conversation.”
GitLab bans internal email in favor of public issues and Slack
“GitLab is very anti-email in a lot of ways. Obviously we use it for external communication, but internally it's on an issue. It's in Slack or it goes into the handbook, right?”
Remote teams can operate successfully with zero working-hour overlap via asynchronous communication
“If he's communicating asynchronously and giving clear outcomes and empowering the people who make the decision, it's okay that they may not have overlap.”
GitLab pivoted from a breadth-first to depth-first product strategy in 2023
“Now, last year we made the conscious decision to start to pivot to depth over breadth. And that's because we have a very broad platform today. We are touching everything from business continuity planning and OKRs to Enterprise agile planning and team planning …”
Founders should only pivot to product depth after proving product-market fit
“I occasionally will have founders reach out and ask the question, when do I make that pivot? And it's really like, have you found your fit in the market? And have you done the whole, and I'll, you will use like, you know, Jeffrey Moore's book, the crossing the…”
Forcing all product features into a single LLM reduces overall feature quality
“What sometimes people will do is they go, oh, there's this really popular, large language model, whether that's a commercial or open source, and then they make everything fit into it. And what you end up doing is actually reducing the quality that someone can …”