Director of Engineering

Stumbling into chaos

The new director of engineering at a startup had to jump in on day one when the team had just done a re-org and re-oriented the product roadmap. He met with the CTO and engineering leads to understand why the new structure had been put in place, then worked with the product managers to focus on pieces they had high certainty of needing. He also added weekly planning meetings for each product team and daily standups to create structure and accountability. Through retros and feedback, he tailored these initial short-term fixes to their needs. He learned that plans often go awry and we have to adapt, look for short-term engineering work when long-term plans change, and creating a predictable process cadence can help create stability.

Changing Companies to Reconnect with Tech

After switching from engineering to project management in 2011, the author felt disconnected from the technical side of their work and began to lose confidence in their job. To reconnect with technology and regain confidence, the author changed companies and became CEO of Topscore, a small company where they could spend most of their time coding. After two and a half years, the author returned to a director of engineering role with renewed confidence. The author's experience shows that it is possible to regain lost confidence and that technical skills are not easily lost.

Developing a One-Year Execution Strategy

A new company mission and strategic direction had been announced, but the one-year execution strategy was unclear. To remedy this, the CEO and executive leadership greenlighted a plan to create a one-year execution strategy. Through conversations with the CEO, CFO, and cross-functional team, assumptions and open questions were identified and documented. These were then narrowed down to three objectives and communicated to the team. The strategy was socialized and used for quarterly planning. Lessons learned included the importance of including various people early, staying outside of the weeds, addressing focus issues head-on, overcommunicating, and understanding how different departments use the strategy.

Too Many Direct Reports

The author joined a small company eight years ago and, as the product scaled and more customers were acquired, the team grew and the author ended up with 20 direct reports spread across four teams. This was overwhelming and time-consuming, so the author took it upon themselves to drive the change and create a structure to groom people from IC to management. They mapped their responsibilities, wrote down role descriptions, advertised the roles internally, and provided thorough feedback to candidates. The author was able to take a step back and become more strategically oriented, and found immense enjoyment in coaching managers and being part of their personal and professional growth. They learned that if they see a problem, they should try to fix it and not wait for their managers to do that for them, and that investing in their own people is important.

Scaling Engineering @ Trustly

Trustly has seen significant growth in Europe and North America over the past year, with North America now representing close to half of total group revenue. In response, the Engineering team has doubled in size, expanding to 109 full-time employees across Brazil, Portugal, and the US. The team has evolved their road mapping and planning processes, and formalized the idea of a Technology Tribe to dedicate Engineering resources for Scalability, Reliability, Security, and Resiliency. The team looks forward to continued growth and evolution in 2022.

Discovering and Mapping Your Career Path

This article discusses the importance of breaking down and evaluating one's career path based on five particular fields, The Five P's: Purpose, Productivity, People, Presence, and Plan. It suggests reflecting on what is important to you, what excites you, and what your passions are, as well as determining what type of lifestyle you want and who you want to have around you. It also emphasizes the importance of thinking about your presence holistically and mapping out a plan that blends together your career and personal life. Finally, it suggests creating a design statement and design principles for yourself, as well as assessing your situation annually and quarterly to ensure that your plan is on track.