Measuring your performance as a startup CTO (Seed/Series A stage)
Measuring your performance as a CTO at a Seed or Series A startup is a unique challenge. As the CTO [1], you're typically a founder driving direction and growth by talking to users and building something they want. You're both an individual contributor and a line manager directly responsible for the engineering team. Existing frameworks [2] for individual contributors or engineering managers don’t capture this hybrid role.
After leading teams at Brex, I wanted to adapt the engineering career path we had there to a startup CTO role. I admired our engineering leadership values at Brex and wanted to emulate them in a startup setting.
The following rubric spans five areas I use to reflect on my own role. It is not a formula: each area needs a lagging outcome and a few leading indicators appropriate to the company.
A. Building something users want. Timely delivery of solutions to real customer problems. Tying this to a top-level company metric has typically worked best for me. Some examples that I've used in the past:
- ARR Growth
- Net Revenue Retention Growth Revenue alone can hide weak product adoption, so pair it with retention, expansion, and direct customer feedback.
B. Technical Excellence: Promote a culture of building scalable, maintainable, and reliable systems. The DX Core 4 framework can work here, but the four DORA metrics are often sufficient at this stage:
- Deployment frequency
- Lead time for changes
- Change failure rate
- Time to restore service
Track these as team-level trends rather than individual productivity scores. At this stage, the direction of travel is usually more useful than an industry benchmark.
C. Technical Direction: Shape the product and technical direction for the company. This is similar to bullet A, except on a longer time horizon. I like to measure this by assessing the quality of technical bets/decisions over a long time horizon. For example:
- Technical bets that keep execution as fast as today a year from now.
- Technical bets that simplify the tech stack or keep it simple a year from now.
- Technical/Product bets that add a 10x competitive differentiation in a dimension that users care about (e.g., the ability to host your infrastructure on-premises for enterprises if your competitors don't support it).
D. Recruiting and Growth: Be the primary point person for sourcing, interviewing, closing, and developing engineering talent.
- Filling critical roles while maintaining a high hiring bar.
- Offer acceptance and time to fill.
- Growth of new technical and people leaders.
E. Team Culture: Accountable for the health of the engineering team. Drive growth, development, and calibration of all engineers.
- Team health, measured through regular one-on-ones or lightweight surveys.
- Regretted attrition and sustainable workload.
- Evidence that engineers receive useful feedback and grow in responsibility.
No single number captures CTO performance. Once a quarter, I choose an outcome and a small set of leading indicators for each area, write down the evidence, and identify the weakest one. The rubric is useful when it forces a tradeoff or a change in behavior—not when it gets averaged into another vanity score.
[1] By CTO, I’m referring to the person who the engineering team reports to. In some startups, there’s a CTO (usually a cofounder) who is a better fit as the “chief architect” and hires a VP Engineering / Head of Engineering / etc. to actually manage and grow the team.
[2] Progression.fyi is a good resource for engineering career frameworks.