How to Hire the VP Eng you need NOT the one you want.

5 min readJul 25, 2023

Vice President of Engineering making some moves in the Startup scene. — a VPE in the native startup scene

It's finally time

Congratulations! You have achieved Product Market Fit (PMF) as validated by your strategic customers and recent Series A funding round. Your ragtag group of ~50 people now needs to actually get organized and execute scaling up the business.

As you embark on this exciting new phase, the Vice President of Engineering (VPE) will emerge as an instrumental figure and pivotal hire. They will shape the engineering roadmap, build robust processes, and lead your team with a clear, strategic direction. Their ability to translate vision into practical, executable plans will be pivotal. By focusing on the scalability and resilience of your tech platform, the VPE will drive the technology-forward momentum of your company, setting the stage for your business to reach new heights.

A potential pitfall startups sometimes encounter is the desire to find a ‘unicorn’ candidate. A startup, for example, with 10 engineers, might seek a VPE who can facilitate growth from 10 to 10,000. They aspire to find someone who’s managed sizable teams but is also content to spend significant time coding. While such ‘unicorn’ VPEs candidates may exist, the process of finding and securing one can be a test of patience and resolve, potentially spanning several quarters and necessitating competition with a multitude of other eager companies.

Instead, hire the one your brain needs and not the one your heart wants.

Most likely you need a VPE that can take you from series A through your series C. Bonus points if that's instead an IPO or acquisition depending on your goals. That's typically 2.5 — 5yrs and your company grows from around 50 to around 400 (around 100 under the VPE) and around 20x Annual Recurring Revenue (ARR).

Who needs to be involved?

Let's start with who needs to be in the interview process:

Co-founders: CEO & CTO
Peers: the heads of Product, People, Sales/Marketing
Direct Reports: 1–2 Engineering Leaders
Board: optional

If you are counting that's a lot of rounds. But what about

How many interviews does it take to hire a Googler?

To cut down on the time to hire, Google's staffing team examined past interview data and determined that four interviews…

rework.withgoogle.com

This is one of the definite times this does NOT apply.

What to ask (Company)

Step 1 — Does the VPE start with the customer? Ok, proceed to Step 2

Step 2 —

Below is a table describing what each position expects from the VPE

Ask the questions to determine if the VPE has the skills AND aligns with the company culture, mission, and goals. Some examples are below -

CEO: Clear Company Vision:

How do you envision aligning the engineering department’s technical strategy with the overall company vision and growth plans?

CTO: Technical Leadership:

Can you provide an example of a technical leadership initiative you implemented in a previous role that significantly impacted the success of the engineering team and the company?

Head of People: Technical Leadership:

How do you foster a culture of technical leadership within the engineering team to encourage innovation, mentorship, and career growth?

Head of Product: Technical Execution:

How do you ensure effective communication and collaboration between the engineering team and the product team to deliver technical solutions that align with product goals?

Head of Sales/Marketing: Product Alignment with Market Needs:

How do you involve the engineering team in understanding customer needs and market demands to ensure that product development aligns with market requirements?

Engineering Managers/Directors: Clear Vision and Direction:

How do you communicate and ensure that the engineering managers and directors are aligned with the long-term technical vision and direction of the company?

Stable Diffusion, and you do not need to have this face in the interview

What to ask (VPE)

As the Vice President of Engineering (VPE), there are several critical aspects of the company that I would want to know to effectively lead the engineering department and contribute to the overall success of the organization. Here are 10 key things I would want to know:

1. Company Vision and Mission:

What is the company’s long-term vision and mission, and how does the engineering department align with these goals?

2. Product Roadmap:

Can you share the product roadmap, and how the engineering team’s technical strategy aligns with the upcoming product development and enhancements?

3. Current Engineering Team:

What are the current size, skillset, and strengths of the engineering team, and what opportunities for growth and improvement do you see?

4. Technical Stack and Architecture:

What is the current technical stack and system architecture, and are there areas that need optimization and scalability improvements?

5. Development Processes and Methodologies:

How are development processes and methodologies structured within the engineering team, and are there any areas for process improvement?

6. Company Culture:

Could you describe the company culture, values, and work environment, and how can the engineering team contribute to fostering a collaborative and productive atmosphere?

7. Market and Industry Landscape:

What are the latest market trends, competitive landscape, and industry challenges, and how does the engineering team stay informed to anticipate customer needs and market demands?

8. Funding and Financial Health:

Can you provide insights into the company’s financial situation, burn rate, and funding status, and how does this affect resource allocation and budget planning for the engineering department?

9. Key Performance Indicators (KPIs):

What are the key performance indicators (KPIs) for the company, and how do they align with the engineering team’s objectives and contributions to the company’s growth?

10. Cross-Functional Collaboration:

How does the engineering team currently collaborate with other departments (product, sales, marketing), and are there any opportunities for improving communication and synergy between teams to drive better outcomes?

By gaining a deep understanding of these aspects, I can lead the engineering team with a customer-centric approach, ensure technical excellence, and contribute to the company’s growth and success as the VPE.