David DeSanto
Chief Executive Officer, Anaconda. On 1 show, 1 appearance. The Shows tab opens the full record on each.
executiveoperatorauthor@david_desanto ↗LinkedIn ↗anaconda.com ↗
David DeSanto is the Chief Executive Officer at Anaconda, having previously served as Chief Product Officer at GitLab through its IPO. He has more than two decades of enterprise software and cybersecurity leadership experience and co-authored Threat Forecasting.
1shows
1appearances
26statements
5resolved
5supported
0contradicted
100%fully supported
Everything David DeSanto said on any show that made the record, most notable first. Each card names its show and opens the statement there.
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…”
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 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.”
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 …”
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 …”
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.”
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…”
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.”
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 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?”
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…”
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 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.”
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”
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 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 …”
One line per show, most statements first. The link opens David's full record on that show: the calibration, argument clarity, speaking style and every statement made there.
| Show | Role there | Eps | Statements | Record | |
|---|---|---|---|---|---|
 LENNY'S PODCASTLEDGER | Chief Executive Officer, Anaconda | 1 | 26 | 100% 5/5 | full record on Lenny's Podcast → |