It has been one year since I wrote the blog post where I shared the learnings from the first three years of my journey as a first-time technical founder.

2021 was not an exception, and my role as RevenueCat’s CTO kept evolving quite a lot. As expected, my job did not get any easier! There are plenty of learnings and challenges worth sharing and reflecting upon. Given the reception of last year’s post, and considering 2021 was enough of an inflection point, I figured this year deserved its own piece.

Highlights: Growth plans and actual results

I ended last year’s post sharing my goal of scaling the engineering organization by effectively doubling the team. Continue hiring great engineers, maintaining and improving our engineering culture simultaneously.

Metrics (EOY) 2020 2021 (Planned) 2021 (Actual)
Engineering Team 8 ~18 17 (+112%)
Company size 19 ~45 40 (+136%)
Number of cities 14 ?? 28 (+100%)
Number of countries 5 ?? 10 (+100%)
Number of time zones 6 ?? 7 (+17%)

Looking solely at these numbers and accepted offers for 2022, we cannot be any happier. One interesting side effect was decentralization: we doubled the number of cities and countries as we doubled the team. In addition, some team members (including myself) moved to new locations. Being able to recruit talent everywhere was essential in this ultra-competitive market.

Regarding culture, I believe we are in a solid position. The team is more diverse, and we hired both the most senior and the most junior engineers this year. Collaboration and ownership feel great, and even though the environment is still a bit chaotic, we have been able to ship multiple impactful features for our customers.

In terms of structure, we started building an Engineering Management layer and the first cross-functional teams. We also created a squad focused on reliability, which was overdue.

Lowlights: My day to day

I am delighted, given the results and everything that could have gone south. Everything ended up according to plan. However, I think the most interesting part is to reflect on what it took to get here, the challenges, and how my role kept evolving. The road felt bumpy and every week seemed quite different. In terms of my day to day, this year was the most random and the least technical so far. Some of the tasks that were on my plate this year:

  • Hiring, hiring, hiring: This was perhaps the only constant during the year. There was a lot of networking, sourcing, intro calls, interviews, candidate reviews, reference checks… nothing that I had not done before, but certainly not at this pace. Having the support of a fantastic People Team and an aligned hiring panel was life-saving.

  • Project management: At the beginning of the year, before we brought our Head of Product onboard, I was still involved in the specification and coordination of a few product and infrastructure initiatives.

  • Brand awareness: A couple of talks, blog posts, and a decent amount of podcasts.

  • Security questionnaires and SOC 2 preparation: The sales team started closing enterprise deals which typically require a more comprehensive diligence process. While responding to one-off security questionnaires, we prepared for a SOC 2 audit. I wrote about the compliance process here.

  • People management: At some point, I had 12 direct reports in 5 different time zones (my calendar was terrible).

  • Investor relationships: During the first years, I was pretty isolated from investors. Our Series B and a more structured Board of Directors led me to spend more time with them. This turned out to be a good thing since they have been truly beneficial.

Additionally, I pushed the occasional random code (there was one hectic week post-vaccine when most engineers took well-deserved time off), helped with incidents investigation, and even customer support.

Mistakes and learnings

Can you spot the issue after reading the previous section? Yup, it’s obvious. I was juggling way too many things.

I thought I was delegating, but the reality is that I was not doing it well enough. My plate was getting fuller and fuller every day. We needed more people, but hiring was slow and bottlenecked. I lost control of my calendar and email. The metrics said we were doing great, but I could barely keep up. I struggled to focus on the big picture; there were not enough hours in the day.

During one of our board meetings, Anu Hariharan asked me what needed to happen for me to take a couple of weeks off without affecting the company. Not only I believed it was impossible, but I was incapable of visualizing a world where I could take a short vacation. This eye-opening event made me realize how wrong it was for me to be a bottleneck after four years still.

Our Head of People offered me to act as my temporary Executive Assistant. I was reluctant at first, but it changed my life. Working closely with her and learning from her leadership experience, I started to control my calendar again. She also kept me accountable regarding delegation, ensuring I was pushing back and not doing anything I was not strictly required to do. I realized that I needed to be more protective of my time and not so accommodating. It was a change for the team, but they understood and stepped up effectively. I even managed to get out of the on-call rotation for the first time since we started the company!

Looking back on how I got to that point, these are my main learnings:

1. Scaling as a founder means delegating and adapting constantly

What it takes to go from 0 to 1 has nothing to do with what is required for the next stage. Before funding or product-market fit, the founders’ strength of will and sacrifice could translate to the startup’s survival. When it reaches the growth stage, though, it should stop depending on the “doing” of the founders. Instead, the founders must adapt and transform into a company building mode.

This is all basic theory, but it was hard to internalize as a builder myself. Even switching from a “builder schedule” to an “executive schedule” took some adapting. Hiring an Executive Assistant can make a lot of sense at this stage.

The way I’m thinking about it now is quite drastic, but it helps me with ruthless delegation given my builder background. My current framework consists of constantly asking myself, “what should I be doing now not to have to work again?”. Ideally, the engineering team should operate at peak performance, even in my absence. There will always be more work for me.

2. Hiring will always be a priority, and it is hard

Hiring is paramount, and it does not get easier. Momentum, investor intros, world-class recruiters, the way you tell the story and the vision… it all helps. But the market is nuts. Every company is raising money and recruiting good talent. There is no silver bullet for hiring the best people, but every little action compounds. Build the relationship even if the timing is not right. Make sure candidates have the best possible interview experience regardless of the outcome. We had a few candidates referring colleagues to us, which is phenomenal.

My biggest mistake with hiring was my inexperience with the market for some specific roles. We were more or less familiar with how long it would take us to hire backend, frontend, or mobile engineers. But I vastly underestimated how long it would take us to find SREs and Engineering Managers. To the point where not making these hires was straining the whole organization. I had to take more direct reports to be able to hire more engineers, and engineers had to split their time between product development and reliability. We survived, but it was not ideal. We could have benefitted from better prioritization and planning in this area.

3. Executives and good investors are company-changing

The same way YC and early employees were transformative in the early days, surrounding yourself with world-class executives and investors is exceptionally impactful.

Founders have the vision, the intuition, and the expertise in the problem. But most of us have never done this before. In fact, this size is getting very close to the largest team I have ever worked with. It is magical when you learn from executives that have experienced hypergrowth and require little to no management. Hiring these owners that will take things off your plate is one of the biggest levers you can pull. If they are the right ones, they will do the job better than yourself, and delegation will become trivial. It will be evident for the whole team, as they will push the company to the next level.

Similarly, working more closely with our investors was a pleasant surprise. They have seen many companies, common mistakes, problems, and solutions. They can make valuable introductions to other founders or future employees. You can use them to bounce ideas and get candid feedback about your performance. I honestly had my hesitations initially, but I can say now that every board meeting was helpful and full of learnings.

4. Taking care of the personal side

These last couple of years have been tough for everyone. For me, 2020 was not too terrible. It was manageable. After all, I am a computer person, so staying at home did not feel bad at first. But 2021 was when it really hit me. It had been a long time since the last time I had visited my family, and close relatives were getting very sick. It was emotionally taxing. I was coping by working longer hours, and I had not taken any vacation for over a year. This mental state is dangerous and a recipe for burnout.

One of the most significant changes we made was moving out from San Francisco, and in retrospect, we should have done it earlier. The change of environment made me exercise more, spend more time outdoors, and my mood drastically changed. It was noticeable by the team.

For the future, I need to pay closer attention to my mental health:

  • Look for the little signs.
  • Be diligent about making lifestyle changes.
  • Establish better boundaries.
  • Consider therapy.
  • And, of course, take solid (real) vacations.

It takes many years to build something big, and founder burnout is a major risk for SaaS. However, life keeps moving, and balance is crucial for long term endurance.

The VPE search

By mid-year, and after seeing how much my co-founder’s life had improved after delegating functions to other executives, it became clear what I needed to do. I had underestimated the effort it would take to go from 10 to 20 engineers. The engineering team was the company’s biggest team, and there were no plans to slow down its growth. I needed help. We decided to start looking for a VP of Engineering that had experienced similar growth.

Our board told us that a VPE search could take around six months and that the market in 2021 was particularly competitive. At the time, I was unsure if we were still a little early, but we were going to need one by 2022 if we were planning on doubling again. So, knowing that hiring is always a priority, and it is hard, we officially started the process in July.

Hiring executives is a different game than hiring engineers – it is a much slower process. We officially closed our search in November after talking to about 40 candidates. It was pretty mentally draining since it ate up a big chunk of my Q2/Q3 calendar, but it was unavoidable. You cannot delegate these. You have to be exposed to as many different backgrounds as possible to calibrate and nail down what you are looking for. For example, I talked to a decent number of highly skilled war-time VPEs. They were all great, but they are typically hired to rebuild dysfunctional engineering teams from scratch. That was not what we needed. In our case, we needed somebody to complement my technical experience and domain knowledge. Someone that could take the engineering culture that we had built and help us go from 20 to 100+ engineers.

Introductions from our investors and referrals were essential, but I also strongly recommend engaging with an executive firm. They are pricey, but you will get exposed to dozens of candidates. Writing down a MOC (mission-outcomes-competencies) document was a powerful tool for us to align on what we did not want to compromise.

The future

I am beyond stoked for the next stage of RevenueCat. We are planning to double the team again in 2022. The company will look quite different a year from now, but I am looking forward to meeting the new engineers and seeing existing employees scale with the company. I am sure there will be a lot of challenges and learnings, but with the VPE in place and our current engineers and managers, I believe we are in a solid position to reach the goal. I can proudly say that we have built a team of good humans that is far better than what I would have ever dreamed of.

Besides the hiring goals, I want to focus on another couple of areas in 2022. Firstly, I want to rethink our engineering onboarding to make it very deterministic and replicable at scale. It will be critical if we are going to have ~100 engineers in 2023. This also involves evolving our developer experience to make everyone productive and able to ship high-quality software every day. We will need to re-assess our planning and delivery processes too. Additionally, we want to double down our enterprise-grade infrastructure efforts. Our throughput keeps growing (our API is serving more than 600M requests per day), and we want to provide the most reliable and secure platform for app developers to manage their subscriptions.

I hope this post was interesting. If you are facing similar challenges and want to connect and share experiences, please reach out on Twitter or shoot me an email!

Special thanks to all the CTOs that have been kind enough to help, discuss, or teach me something this year. Shoutout to Peter Silberman, Alex Plugaru, Matias Woloski, Tobias Balling, Eddie Kim, Jason Warner, and Will Larson. Our board members Anu Hariharan, Mark Fiorentino, Mark Goldberg, and the early believers Jason Lemkin, Andrew Maguire, and Nico Wittenborn

Additionally, I would like to express, once again, my gratitude to all my colleagues at RevenueCat engineering, the executive team, and my co-founder Jacob. Thank you for trusting me, allowing me to grow and experience this incredible journey.