The Problem
A Series B SaaS company needed to hire its first CTO. The founding team was commercially focused; the current head of engineering was a strong individual contributor who had not operated at the VP or CTO level and was not the right person to assess executive technical candidates. The CEO knew she needed someone senior — but could not define "senior" in technical terms precisely enough to evaluate candidates herself.
This is one of the most common failure modes in first CTO searches: the company knows what it needs but cannot assess whether candidates have it. They default to proxies — school names, company logos, number of GitHub stars — rather than the specific technical leadership capability the role actually requires.
The Assessment Framework
Separate technical depth from technical leadership
A CTO at a 60-person SaaS company does not need to be the strongest engineer in the room. They need to make good architectural decisions, attract and retain strong engineers, and translate between technical complexity and business strategy. The assessment focused on these capabilities — not on whiteboard coding.
Use reference conversations as technical proxy
The most revealing technical assessment is not a problem set — it is a conversation with engineers who have worked for the candidate. Strong technical leaders produce strong teams. The reference pattern we looked for: "I became a better engineer working for them" from at least two former direct reports.
Test technical communication, not technical recall
The CEO needed to work with this CTO daily. The most important technical assessment for a non-technical CEO is: can this person explain technical trade-offs in terms that help me make business decisions? We structured a case presentation — a real architectural decision from the company's product roadmap — and assessed how each candidate communicated the trade-offs.
Bring an independent technical advisor for the final two
For the final two candidates, we engaged an independent fractional CTO (not connected to the search or the company) to have a 60-minute technical conversation with each. Their brief: assess whether the candidate's architectural instincts were appropriate for the company's current technical state and 18-month roadmap. The advisor's assessment confirmed what the reference conversations had indicated.
The Framework for Non-Technical Founders
Non-technical founders hiring a CTO should not try to assess technical depth directly — they are not equipped to do so, and candidates know it. Assess what you can evaluate: communication clarity, team-building track record, business-technical translation skill, and the quality of the engineers who have worked for the candidate. These are reliable proxies for the technical leadership the role requires.
Assessment Framework Summary
What This Search Teaches
When the company cannot run a technical panel — which is true of most first CTO searches — the search firm must build the assessment architecture. That means reference-based technical validation, communication-focused candidate evaluation, and independent technical advisor input on finalists. Substituting CV proxies (company name, school name, press mentions) for actual assessment produces the wrong hire in a predictable direction: someone who looks impressive on paper and cannot build the team the company needs.
Related case studies and resources:
CTO Search: Technical AssessmentWhat Is Executive Assessment?What Is an Executive Reference Check?What Is a C-Suite Search?Founder-VP Fit Model