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Cross-Functional Management: Engineering and The People Team

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Coming from more than a decade of professional software engineering experience, I’m thoroughly convinced that cross-functional teams are the way to win in this field. It’s an agile practice that can be summarized roughly as “form teams around a problem and ensure they have all the skills within the team that are necessary to solve the problem.” When I joined Checkly in 2021, the goal was to scale up our post Series A startup to 3 high-performing engineering teams. To tackle this problem effectively, cross-functional skills were obviously needed. One big part of doing this was to implement new people processes to hire and onboard a fleet of new engineers fast. Therefore, it was obvious that I would have to collaborate very closely with the leader of our people team, Kaylie Boogaerts.

How did we collaborate? It starts with regular 1:1 meetings

As an experienced Engineering Manager I’ve learned that 1:1s are an invaluable tool. It was obvious I needed to set up weekly 1:1s with Kaylie from day 1. That’s a pretty big time investment, so what does a Director of Engineering get out of it you might wonder?

  • Building a strong relationship between engineering and HR: People are not robots, and strong relationships can be invaluable, especially when things get rough or mistakes are made. Yes, I made mistakes and it was good to know that our people team leader had my back.
  • Getting free coaching: Kaylie is an excellent coach and often helped me gain a different perspective on problems I wanted to tackle, or gave me confidence with my approaches. Ask a people lead for help and you might be surprised.
  • Process alignment: In an early stage startup, product engineering usually is the biggest department, so performance frameworks, documentation, tools, etc. mostly impact engineering. As a team, introducing and enforcing new processes with one voice was key to success.
  • Tackle side projects together: In a small startup you constantly have to stretch and go beyond what is expected of you. Getting SOC 2 compliance was a major effort for the company that needed engineering, operations, and the people team to work together.

The outcome: Alignment between people, company culture, and how engineering is managed

Today it is absolutely normal for Kaylie and I to plan together what’s next for Checkly. We share what’s on our plates and how it will influence each other’s work. I try to understand how I can support people initiatives from the engineering side and she does the same for me.

Below you can see a fun example for how aligned we are these days. I gave some praise on Slack to an engineer resolving an incident on their own initiative. The moment I sent the message I had a voice in my head reminding me to reinforce that we care about work life balance. Kaylie sent me a message 3 seconds after I made the edit.

More results!

Here are some additional results that Kaylie and I achieved working together (for those who might like reading about them):

  • Transparent pay framework: It’s a people initiative, but of course engineering is mostly impacted. I wrote the role descriptions and engineering level expectations, Kaylie created salary benchmarks, did all the math and as a team we aligned all of this to create our Checkly pay calculator.
  • A well-defined and fair performance framework: We have well-defined engineering levels, a performance and career progression framework and fair payment. All of this together takes a lot of bias out of our processes and our adjusted pay gap is 0.
  • Commitment to DEI and hiring diverse teams: Together Kaylie and I created a thriving engineering team with diverse members regarding gender, age, seniority, and other factors. I remember Kaylie checking my job posts for intimidating language or discussing insights from our DEI surveys with me. We also held a cross cultural communication workshop together at a company retreat in Barcelona.
  • High retention: The average tenure at Checkly engineering is 1.5 years, considering the company itself is only 5 years old and we started hiring most engineers in the second half of 2021, that is pretty impressive. In addition, our last company-wide employee satisfaction survey showed an eNPS (employee Net Promoter Score) of 69. Most companies say 0-30 is the safe zone and that a result above 30 is excellent. Through strong feedback culture, enforcing a healthy 1:1 culture and our combined efforts we made this happen.
  • SOC 2 in record time: In Summer 2022 our CEO kicked off the discussion for Checkly to become SOC 2 compliant to prove our high degree of information security and data privacy to customers. This was a major project that touched all departments. As a cross-functional management team, working with agile project management we had all the skills needed to pull this off together in less than 5 months. For collaborating on writing necessary documentation, implementing process changes, writing policies, and getting buy-in from Checkly employees, it was crucial for us to work as a team. After pulling this off next to successfully scaling engineering, I am confident we can solve any problem.

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