How to hire your first VP Engineering

First Off: What Does the VP Engineering Do?

  • articulate the priorities for making these decisions
  • help judge the trade-offs
  • settle disputes regarding architecture
  • step in and make decisions that span multiple eng teams, especially if the teams disagree
  • refining processes to ensure a high development velocity
  • adding software best practices to keep the bug count low
  • collaborating with the business team to ensure technology will help hit business goals
  • setting a roadmap to create innovative technology that acts as a sustainable advantage over competitors
  • create structure for career paths and promotions
  • build a diverse team with an inclusive environment
  • manage team morale
  • prevent conflicts (and resolve the ones that couldn’t be prevented)
  • create an environment where engineers feel a high sense of fairness in how people are given responsibilities, promoted, and guided in their growth
  • maintain high productivity, such as by matching tasks with engineers’ interests and strengths

When Do You Need to Hire a VP Eng?

  • Technology (architecture decisions):
  • Are your engineers fighting frequently over technical architecture and getting into stalemates?
  • Do your engineers talk about how your codebase has high technical debt or how there’s a lot of spaghetti code?
  • Do tasks consistently take longer than expected because the engineers say the code is brittle or hard to understand?
  • Do engineers often uncover many problems in the course of fixing a narrow issue?
  • Do non-technical people end up serving as a tie-breaker on technical decisions?
  • Leadership (software development process & collaborating with other departments)
  • Is software development velocity consistently too low, compared to other companies using similar technologies and solving similar problems?
  • Does your production website have 2+ user-visible significant errors per week?
  • Does your production website have an outage more often than once per quarter?
  • Is the business team repeatedly holding back on making requests (and instead using suboptimal workarounds) to tiptoe around 1 or 2 “grumpy” senior engineers?
  • This is especially concerning if the CTO or current head of engineering is one of these grumpy engineers.
  • Are the engineers unclear on the vision and roadmap for Engineering?
  • Are other departments (e.g. Marketing, Operations) unclear on the roadmap for Engineering?
  • Does the business team think that the engineering department is working on “tech for the sake of tech” and is not working on the most important priorities to drive the business forward?
  • Management (careers, people management):
  • Is there an increasing amount of conflict between engineers?
  • Are a significant number of engineers demoralized?
  • Have you experienced unwanted attrition of several engineers?
  • Is there a “clique”? Do engineers complain that there’s an in-group and an out-group?
  • Do you have a non-diverse team? Do you get complaints from the few underrepresented engineers about the team environment?
  • Is there tension and uncomfortable silence in many engineering meetings?
  • Are there low performers whose performance is not getting addressed?

Decide Which Stage of VP You Need

  • VP Eng is writing code most of the time, and doing people & project management in the remaining time. This happens when the eng team is still one cohesive team rather than subteams, typically 10 engineers or fewer.
  • When interviewing, cover technical architecture, coding, software development process, and managing ICs.
  • VP Eng understands the codebase and is managing managers. They read through some of the changelists submitted by engineers. They spend their time on strategy, roadmap, and software development process. They may occasionally write non-critical-path code. There may or may not be a promotion system or career ladder. This is typically 11 to 30 engineers.
  • When interviewing, cover how they lead the software development process, create a culture for technical excellence, and manage managers.
  • VP Eng is one step removed from the codebase, and relies on directors & managers to make technical decisions for each codebase component. They are in charge of the career / promotion ladder. They also create the annual budget, OKRs, and strategize the 2–3 year technology roadmap. This is typically 31 to 100 engineers.
  • When interviewing, cover how they set the yearly engineering roadmap, handle promotions and career paths, and create a culture for technical excellence when there are many independent teams.
  • VP Eng manages technology for multiple product lines. Their reports (directors) present them with choices on areas spanning roadmap, org design, headcount, and in which areas to invest development. They make the final decision. This is 101+ engineers.
  • When interviewing, cover how they do long-term org design, set the 3+ year technology roadmap, and assess industry trends in order to create a sustainable technology advantage over competitors.

Interviewing Candidates for VP Engineering

Pitfall to Avoid: When Interviewing, Don’t Accept Hypothetical Answers

If You’re Hiring for Complementary Skills, Don’t Lose Sight of That

Confidence and Bluster

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