20VC Gitlab Founder, Sid Sijbrandji on Lessons From Scaling from 400 to 1,000 People in 1 Year, Why You Have To Have A Low Level Of Shame On The Product You Release & The Secret To Making Remote Work So Effectively At Scale

In this episode of "20 Minutes VC," host Harry Stebbings interviews Sid Sijbrandij, founder and CEO of GitLab, a comprehensive software development platform. Sid discusses GitLab's unique approach to integrating the entire software development cycle into a single application, which has attracted over $145 million in funding and grown to a fully remote team of 762 members across 55 countries. He emphasizes the importance of transparency, iteration, and community in building a successful product and company. Sid also touches on the challenges of creating a remote work culture and the necessity of clear communication, documentation, and social trust-building. Despite the company's vast product scope, Sid remains committed to improving and refining GitLab with the help of a dedicated team and an engaged community.

• Harry Stebbings introduces Sid Sijbrandij, the founder and CEO of GitLab.
• GitLab is a single application for the entire software development lifecycle.
• Sid has raised over $145 million in funding from notable investors.
• GitLab has scaled to over 762 team members in 55 countries, operating as a fully remote team.
• Sid is known for his openness and transparency in building the product and company.
• Harry Stebbings recommends the GitLab handbook as a must-read.

"I'm super excited to welcome Sid Sid Brangy, founder and CEO at GitLab to the hot seat today."

This quote introduces Sid Sijbrandij as the guest on the show and sets the stage for discussing his experience as a founder and CEO.

• Sid started in software development and discovered GitLab, which had a strong community of contributors.
• He recognized the potential for a SaaS version of GitLab and started GitLab.com.
• Initially, the SaaS product was not as popular, but there was demand for new features in the self-hosted version.
• Sid partnered with Dimitri, the original author of GitLab, by funding him to work on the project full-time.
• Today, GitLab has improved its SaaS offering, but the majority of revenue still comes from self-hosted solutions.

"I actually tried to get into the world of SaaS, and I got into the world of software instead."

Sid explains his initial goal was to enter the SaaS market but ended up focusing on software, leading to the creation of GitLab.

• Sid discusses his approach to trust and risk when collaborating with others, especially in the early stages of GitLab.
• He emphasizes the importance of managing risks and avoiding significant damage to the organization.
• Trust is balanced with the need for people to prove themselves within GitLab.

"I think I try to trust especially, look, if it doesn't work out, it's not the end of the world."

Sid reflects on his attitude towards trust in business, indicating a willingness to take risks as long as they are manageable and not detrimental to the company.

• Harry Stebbings inquires about GitLab's unique organizational structure.
• The discussion on organizational structure is intended to provide context for the rest of the conversation.

"I do want to start with the organization and just set some context ahead of time because it's a very special structure you have in place."

Harry Stebbings prompts Sid to discuss the organizational structure of GitLab, noting its uniqueness and relevance to the conversation.

• GitLab currently has 650 people, growing from 400 and aiming for 1000 within the year.
• The company is all-remote with employees working from their preferred location, often from home.
• GitLab supports remote work with tools like Zoom, Slack, Google Docs, and their own product.
• There are no shared offices, and collaboration spans across more than 50 countries.

"GitLab is now 650 people. We're growing this year from 400 to 1000 people. And one of the particular things about it is that it's an all-remote company, so everyone works from the location they prefer."

This quote explains GitLab's current size, growth trajectory, and its distinctive all-remote work policy, which allows employees to work from any location they prefer.

• Transparency and iteration are crucial for asynchronous work across different time zones.
• Iteration involves reducing scope and delivering smaller increments quickly, which requires less coordination.
• Transparency eliminates the need for constant communication, as information is readily available and documented.
• GitLab maintains a public, extensive handbook of over 3000 pages to facilitate this transparency.

"The hardest part from working across time zones is that it needs to be asynchronous. You have to be able to collaborate without being in a meeting at the same time."

This quote emphasizes the importance of asynchronous collaboration in a remote work environment where employees are spread across various time zones.

"Iteration reduces the coordination cost and it's a core value at GitLab."

The speaker highlights the value of iteration in reducing the need for coordination, which is a core principle at GitLab.

"At GitLab, we write a lot of things down. We have a handbook, it's public and creative commons."

This quote explains how GitLab uses extensive documentation to facilitate transparency and reduce the need for direct communication.

• GitLab focuses on results rather than hours worked, with accountability for outcomes being a top value.
• Smaller steps in development reduce the risk of failure and allow for easier adjustment based on feedback.
• Ambition is encouraged, but with a structure that minimizes the fear of failure due to the iterative approach.

"There is accountability for results at GitLab, very much so. Results is our number one value."

The quote underlines GitLab's emphasis on results and accountability as its primary value, ensuring that employees are responsible for their output.

"I think what you want to reduce is failure. And I think because we take smaller steps, there's much lower risk of failure."

This quote explains the company's strategy of taking smaller steps to minimize the risk of failure and promote a culture of ambition without fear.

• GitLab's transparency extends to compensation grids and product roadmaps.
• There is a slight negative in competitors seeing plans, but it is outweighed by the benefits of customer feedback and correct roadmaps.
• Open product roadmaps enable better customer influence and ensure that GitLab builds what customers need most.

"The most important thing about your roadmap is not that it's a secret, but that it's correct that you're making the stuff that customers want."

This quote highlights the philosophy that an accurate and customer-focused product roadmap is more valuable than keeping it secret from competitors.

• GitLab is a single application for the entire DevOps lifecycle, a scope that evolved over time and now exceeds that of competitors like GitHub.
• The integration of different tools into one product was not initially obvious but has since become a key differentiator.
• The story of integrating version control and CI (continuous integration) illustrates GitLab's approach to product development and breadth.

"GitLab is a single application for the entire DevOps lifecycle, which means that all the way from planning what software you're going to build to rolling it out, monitoring it and securing it, you can do that all inside one product."

This quote describes GitLab's comprehensive approach to product development, offering a single application that covers the entire DevOps lifecycle.

"Dimitri said, you're obviously wrong, by the way, I just made an edit that we should never use the word obviously because it discourages people from challenging what you just said or asking for clarification."

The quote reflects GitLab's culture of open communication and continuous improvement, where even the use of certain words is reconsidered to foster a more inclusive and collaborative environment.

• Dmitri suggested bundling two separate industry-standard products into one.
• Sid initially disagreed with Dmitri, citing industry norms and perceived lack of user benefit.
• Dmitri argued that a single product would be more efficient due to a unified release process.
• Sid eventually agreed, and the decision proved successful with users appreciating the integrated approach.

Anyway, he was told by Dmitri, he was obviously wrong, but he didn't take no for an answer. He kept pushing and at a certain point it came to me and I also said, look, this doesn't make sense. Everyone in the industry does this as two separate things.

Sid was initially skeptical about Dmitri's idea to combine two products into one, as it went against industry standards.

He said, well, if you don't believe that, at least believe it's more efficient to us to ship it as a single product because we'll only have one release process.

Dmitri argued that a single product would streamline the release process, aligning with the company's value of efficiency.

• The concept of concurrent DevOps was born from the integration of two products.
• It eliminated the need to manage projects across multiple applications, saving time and reducing errors.
• Concurrent DevOps allows for simultaneous work on different aspects of a project, such as code writing and security testing.
• The success of this approach led to GitLab expanding its scope to cover more stages of the development process.

And we call that concept now concurrent DevOps. And it means that you don't have this passing the hot potato between ten or 20 different DevOps applications. But at any time anyone can work on anything.

Concurrent DevOps is a methodology that allows for seamless collaboration and workflow across various stages of software development.

• Sid believes that great businesses are either bundling or unbundling services.
• GitLab chose to bundle its services, which goes against the common advice of maintaining focus and simplicity.

I think it's more every great business is either bundling or unbundling, and we're in the bundling business.

Sid explains that GitLab's strategy is to bundle services, which he sees as a common trait among successful businesses.

• GitLab releases new features in small iterations, even if they are not fully complete.
• This strategy encourages community contributions, which improve and refine the product over time.
• The concept of having a low level of shame is about prioritizing progress and collaboration over perfection.

So sometimes the stuff we release, we have a low level of shame about them. They're not complete and we know it, but it allows people from the community to come in and contribute to it.

Sid acknowledges that some of GitLab's releases are not fully polished, but this openness allows for community engagement and continuous improvement.

• The GitLab community originated from humble beginnings with Dimitri's simple project.
• Maintaining community engagement is challenging but essential, as it can be easily lost.
• GitLab ensures community engagement through transparency, such as openly discussing pricing and company values.

So the community was there because Dimitri started this thing from very simple beginnings.

Sid credits Dimitri for establishing the initial community around GitLab.

So we have our stewardship promises, things that we saw going wrong with other projects, and that will promise never to do.

GitLab has made commitments to avoid certain pitfalls observed in other projects, fostering trust within the community.

• Transparency is a core value and strategy at GitLab.
• Sid argues that it is more harmful for a company's employees not to know the strategy than for competitors to be aware of it.
• Publicly sharing the strategy helps align both current employees and potential recruits with the company's goals.

Transparency started as a value because it was really important to keep in touch with the community. Later on, we realized it's also a great way to recruit people who are aligned with what you do.

Sid discusses how transparency began as a means to maintain community relations but also became a recruitment tool.

We choose to say, okay, we're just going to be very public about our strategy.

Sid explains GitLab's decision to be open about its strategy, which ensures internal and external alignment.

• Sid found that an all-remote team is more feasible than a hybrid model.
• Remote work necessitates better communication, documentation, and training practices.
• GitLab has developed mechanisms for building social trust among remote team members.

I think it is much more doable to be all remote than I thought.

Sid reflects on the unexpected ease of managing an entirely remote team compared to a hybrid setup.

Good business practices like documentation and training. Also, you got to take care of organizing the social trust building.

Sid emphasizes the importance of solid business practices and social interactions in building a successful remote team.

• Informal communication is crucial when managing an all-remote team.
• Facilitating non-transactional relationships outside of core processes is beneficial.

So there's a lot of things in which you kind of have to facilitate the informal communication.

This quote emphasizes the need for deliberate efforts to encourage informal interactions among remote team members to foster a cohesive work environment.

• "High Output Management" is recommended reading at GitLab.
• The book is considered the best management book by the speaker.

We recommend high output management at GitLab.

Sid Sijbrandij suggests that "High Output Management" is a valuable resource for understanding management principles, signifying its importance in the GitLab culture.

• GitLab pays people different rates based on local markets.
• A blog post explains the rationale behind local rate compensation.

We pay people differently. We have a blog post about it. Why we pay people local rates.

Sid Sijbrandij acknowledges that GitLab's compensation strategy takes into account the local cost of living, which is detailed further in a company blog post.

• Sid disagrees with the notion that "you can do anything you want."
• He believes in focusing on what you're good at, enjoy, and for which there's demand.

You can do anything you want.

Sid Sijbrandij disputes this common piece of advice, suggesting that success is more likely when aligning personal strengths and market demand with one's passions.

• Security roles are generally hard to hire for, but GitLab's team is performing well.
• Currently, the most challenging role to fill at GitLab is in sales.

We're furthest off with our sales hires.

This quote reveals that GitLab finds hiring for sales positions particularly difficult, despite having a competent security hiring team.

• Sid experienced an inflection point realizing the superiority of an integrated product.
• GitLab's integrated version control and CI provided a better user experience than separate products.

It was really counterintuitive to see how an integrated product was better than different products working together.

Sid Sijbrandij reflects on a pivotal career moment when he understood the value of product integration, which contradicted his previous beliefs.

• Monetization should begin when there is significant usage and demand for enterprise-specific features.
• GitLab uses a "buyer based open core" model for monetization.

When you get a lot of usage.

The quote indicates that a large user base with enterprise-specific feature requests is a signal to start monetizing an open source community, as experienced by GitLab.

• GitLab releases updates on the 22nd of each month.
• The date remains fixed while the scope is variable to meet deadlines.

We release on the 22nd of every month.

Sid Sijbrandij explains GitLab's consistent release schedule and the strategy of adjusting the scope of work to adhere to fixed deadlines.

• The goal is to improve product areas that are not as strong as version control and CI.
• GitLab plans to increase engineering staff and continue leveraging community contributions.

We have a lot of scope right now in the product.

This quote outlines GitLab's ambition to enhance their product offerings and the strategic steps they are taking to achieve this, including expanding their engineering team and encouraging community involvement.

• The host expresses excitement for GitLab's future and appreciation for Sid's participation.
• Listeners are directed to find more information about Sid on Twitter and about the host on Instagram.
• The host mentions the benefits of sleep optimization and introduces sponsors with solutions for personal and professional growth.

Thanks. It was my pleasure. Thanks for the great questions.

Sid Sijbrandij closes the conversation by thanking the host for the insightful discussion, highlighting the positive exchange of ideas during the podcast.