How to: Choose the Right VP of Engineering

Name Tim Shieh Platform Associate at Pillar VC

No matter whether you’re just starting to build a business, growing a company, leading a major corporation, or anything in between, technical leadership will be one of the most important decisions and hires you make.

In today’s software-driven world, many companies are being founded by technical founders themselves, but that’s not always the case. What should you do if you yourself cannot be the technical leader of the organization, or if you need to find a new one? Who should you hire, partner with, and consult about technical issues? How do you know you’re making the right decision when you bring a VP of Engineering on board?

As with most things in business, the answer largely depends on you. There are a few core questions you (or your executive team) need to answer that will drive the profile for which you’ll be searching. If you can answer these questions honestly, you’ll have a pretty good idea of what to look for:

What stage engineering team
do you have now?

This aligns with an article we wrote back in March about what you should expect at different engineering team sizes and stages. The takeaway here is that leaders of smaller engineering teams can – and tend to be – more technical and hands on, but as the organization scales, the company will naturally demand someone with more business acumen and stronger managerial experience.

As a startup, with just a few engineers, (or maybe not even yet!) your engineering leadership needs to be a contributor as well, working as a member of the team in addition to its nominal leader.

As your company grows in size, your VPE’s role will change. By the time the team grows past about 50 engineers or so, your VPE will be managing managers, and will need to spend a lot more time fighting business fires than technical ones.

What stage is your company right now?

In addition to team size, you have to consider the stage of your company from a market standpoint. Do you have a product in the market, or are you just trying to get something built?

If your focus is primarily building a new product, you might consider bringing someone on board who has some amount of product instinct – you want someone who can help you actually invent the thing.

If you are already in the market, how many people are using your product? Do you have a long running set of commitments to existing customers? Do you have Service Level Agreements that you need fulfill? How much are you inventing right now vs. maintaining? Do you have the right technical systems in place to support these demands? If the answer to that last question is no, or I don’t know, chances are you’ll want to look for someone who can take on a slightly more technical role and directly support those systems–things like the database and infrastructure that the product will rely on.

How frequently will you release new product?

You need to assess the frequency of change that your customers will be willing (or expecting) to take on. Is the product you’re building SaaS? Are you building something that on-premise? Do customers expect you to constantly build new features and update the product for them, or would that place an undue burden and drive them away?

Know the backgrounds of the engineering leaders you speak with and make sure that their former experience aligns with the speed of change expected at your organization. Chances are that even a seasoned pro coming from an established hardware firm will have a hard time adjusting to the demands of a cloud software company. Choose an engineering leader who can support the cadence of growth for your product.

What type of product or industry do you operate in?

The market for the software you are building will have a big impact on who you’ll want to hire to lead your engineering team.

This may be an overgeneralization, but take for example consumer versus enterprise software. The technological challenges of consumer software may not be exceedingly difficult to overcome at first, but the way you understand those consumers should be advanced. In this case, an engineer leader with more of a product focus or consumer instinct may be the right choice. Alternatively, heavy tech companies need engineering leaders with less of a product lens and who are more equipped to overcome complex technological problems.

What do you want to be when you grow up?

In addition to assessing the stage of your company right now, you’ll want to have an opinion on where you want to be a year from now. Look at companies that you aspire to be like in one year, and find people who have a level of experience to match that profile. After all, you don’t want to hire for the team you have–you want to hire for the team you want to have.

Having said that, a lot of companies will fumble at this point by overreaching and hiring not one, but two stages ahead. This can be problematic. Too often I meet founding CEOs with 5 or 10 employees who say they want to be the next Airbnb, and who excitedly hire a big deal VPE or CTO.

The issue is that these companies cannot feasibly be the next Airbnb in just one year, and those leaders are not used to getting the product out of the garage, rather they are really good at leading large, developed teams. These big-deal leaders need project managers, admins, and full DevOps teams to be in place underneath them, putting processes in place that aren’t nimble enough – all of which will end up having you over spend and slow down prematurely. Or, in the absence of that budget, they sit idly by, unable to get anything done. When that doesn’t work out, the founders swing in the opposite direction, now with a 30 person engineering team who needs some good process in place, but hire someone who wants to tinker and is not able to see the big picture.

Be honest with yourself about where you are and where you want to be realistically in a year, and hire for those parameters.

Why are you making a change?

IIf you are just starting out, something must have prompted you to decide to hire an official VPE. If you’re not just starting out, chances are something has not gone as planned for you to be looking for a new VPE. Are services going down? Are you missing timelines and commitments to customers, are you not getting v1 out the door? Each of these problems will help to clearly identify different profiles of leadership to look for in order to successfully right the ship.

Who will best fit with the team's style?

In this case, fit means nothing about the person’s ability to get along with and work with the other members of the management team. The question is your team’s style.

Is the rest of your management very executive in terms of interaction with the rest of the company? If so, you’ll need someone who understands upper management and liaising between them and others in the organization. If your team is more casual and scrappy, that same executive-type person might impede the natural flow of information throughout the company.

Ultimately, the person you hire should have the right mix of experiences and inclinations to match your company’s size, technology, and maturity. My number one rule is always that people can surprise you, so talk to as many people as you can, and hopefully you’ll find that one great fit that helps you take your engineering team and your company to the next level.