CTO

IC to CTO, Coding to Not Coding

After transitioning from an individual contributor to a CTO and founder of a startup, the author questioned whether they wanted to remain in the leadership role or return to coding. After gathering data and talking to people they respected, the author decided to stay in their C-level role and picked up side projects to satisfy their coding hunger. The lessons learned from this experience are to gather data to make the right decision, accept the shift in responsibilities, and add incremental value to the team.

Discovering Non-Traditional Pathways to Success

This is the story of a software engineering intern who, without a college degree, worked his way up to become the CTO/co-founder of a startup. He began tinkering with technology in middle school and continued to develop his skills in high school and college. He joined a startup through an online tech group and worked with the CEO to develop a product that would give users cashback rewards for paying with their bank. Through many iterations, he grew into the team lead position and eventually the VP of engineering, helping to manage the product and find the right product-market fit.

The Ambiguous Role of a CTO

The role of a CTO is often difficult to understand, as it can involve managing people, technology, or customers. It is important to understand the distinct approach to the role that is context-dependent and varies from company to company. It is possible to be good at all three, but it is impossible to be great. It is important to find an alignment between what you like and what you are good at, and to hire people to fill in the other positions or allocate those responsibilities to other managers. Introspection and understanding what kind of CTO you are/should be is key, and multitasking is never a good idea.

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.

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.

Drawing the Line Between the Roles of a CTO and an EM

A small company with less than 20 engineers needed to formalize the role of a de facto manager, and the CTO and the EM had to decide where the boundaries of their roles should be drawn. They agreed that the CTO would handle external matters and the EM would be responsible for internal matters, but there were many exceptions. The transition took three to four months and the EM learned a great deal about how to structure the team and organization. They also learned that being a manager can be a lonely job and that different companies have different needs and titles with different responsibilities.