Hiring The VP of Engineering
You're hiring the conductor of the orchestra rather than a virtuoso performer.
Many tech companies are founded by engineering leaders. In the early days, the engineering team is often run by the founding CEO or CTO. That can be a good way to run things in the early days, especially if it’s a team that has worked together before.
If you’ve got a founder or front-line engineering manager in place, you can likely scale to a few dozen people. You need to be setting goals for people, giving feedback and building processes that ensure good collaboration without too much overhead or rework.
Once the team grows beyond the scale that interests a highly technical founder, it's important to recognize the impact. The need for coordination and communications grows with every new hire. You’ve got to reconcile different technical approaches, manage personalities and make sure you’re making steady progress towards goals.
At this stage, there’s sometimes a desire to hire a “people manager,” presumably to manage HR issues like compensation and vacations so that the founder can focus on coding. It’s an interesting idea, but it never works in practice, because you can’t manage technology without managing the people who build it. If you hire a caretaker, you’ll find yourself with a mediocre team that doesn’t believe in their manager. Even worse, you won’t be able to hire great talent, because they want to work for a great VP.
As you move from a working prototype to a real production system, the number of technical issues you’re dealing with expands exponentially. There are multiple different functions that require coordination, for example, separate front-end or back-end teams, testing, dev ops, documentation, not to mention coordinating with marketing, sales and support.
There are decisions about how to balance new feature development with bug fixes and performance improvements. You’ve got to manage the cost and performance of cloud services, tackle make versus buy decisions, determine when to use open source software, how to implement management and monitoring, security reviews etc.
Enterprise = More Complexity
In the early days, a lot of things are done informally without much process. That’s fine with a small team. But as you expand into Enterprise customers, there’s a maturation that’s needed. Customers will want a detailed roadmap, security reviews, customizable Access Control Lists (ACLs), SOC-2, GDPR and many other acronyms. The Minimum Viable Product (MVP) approach that works in the early days doesn’t work with larger customers. They aren’t looking for minimum viability, they’re looking for solutions to their problems and maximum commitment!
Enterprise customers are making a career bet when they buy from you and you need to be prepared to deliver. Features that are easy to solve for small customers can be much more complex with larger enterprise customers who have large numbers of users, conflicting needs and a myriad of integration and reporting requirements.
If the number of issues is exploding, it’s probably time to hire a VP of Engineering. For your first VP, you need someone who can be hands on in three key areas: making sure you build the right product, develop the right processes and nurture the talent. Each of these areas needs to become Enterprise grade.
The VP of Engineering needs to be able to make good architectural decisions that affect performance, agility, scale and security. They also need to weigh in on tools and processes used to build your product. Who’s working on what? What are the checkpoints? What are your processes for testing? How do you review quality, completeness and performance?
You’re looking for someone who can listen to the input of engineers, customers and founders and make good decisions. They must be able to add value, not just adjudicate different views. If they can’t make tough decisions, they can’t be a manager, let alone a VP. As the company ramps it’s product management function, they need to be comfortable sharing more of roadmap decision making in a highly collaborative fashion.
The best managers provide focus and amplify the work of others. They can tackle hard decisions without panicking, they are fair and they ship great quality software that customers love.
Hire for Scale
So how do you find this person?
First of all, make sure they have done the job you have today and the job as you expect things to scale over the next two years. If you’ve got 25 engineers today, you want someone who can manage the team today and has headroom to grow to 50 or 80 engineers with multiple teams and locations over time. Don’t hire the person who is running a 500 person organization out of Google, Facebook or similar. Unless they’ve come in through an acquisition of a startup, they won’t be effective or sufficiently hands-on in a startup.
One common mistake is to confuse the VP of Engineering role with the CTO. The VP of Engineering does not need to be the most brilliant software architect. Rather the VP needs to be able to work with the CTO, and manage the myriad of personalities that exist in an Engineering organization. The VP of Engineering is more of the conductor of the orchestra, getting everyone to play their part as best they can, rather than a virtuoso performer.
Look for candidates with a proven track record of managing teams (and ideally teams of teams) and shipping great software that has withstood tests of time and scale. You want to uncover examples where the candidate’s impact was through planning, leadership and coaching rather than individual heroics.
They should exhibit natural curiosity that shows they care about people and technology. Did they investigate your APIs? Did they download your open source modules? Did they sign up for a demo? Do they have opinions about about how your product could be improved? They should be a builder, and they should be leaning in and demonstrating interest.
If you can hire someone with relevant domain knowledge that’s the best. If you’re building infrastructure software you need a leader who comes from that world. If you’re building B2B SaaS apps, get someone who understands that world, the customers and the competitors. While it’s not an absolute requirement, it will shorten the ramp time if they already have some familiarity with the space.
If you don’t have much experience hiring executives in this area, it’s good to interview more candidates than fewer. It becomes easier after a few meetings to start to determine what is most important to your company. You can start to distinguish between what is essential for your situation and what is “nice to have.”
Real World Problems
I often find the best approach is to focus on the current and recent challenges in the area and ask for input and advice on how they would deal with the situation. These shouldn’t be theoretical examples, but real world issues that you’ve experienced or are considering. For example:
What would you do to improve uptime and reliability?
How have you managed spikes in cloud costs?
What would you do to reduce the risk of a potential breach?
How would you prepare us for SOC-2?
How have you increased team velocity?
How have you evolved an organization from MVP to scale?
How have you managed early engineers who weren’t experienced enough to tackle the next phase of growth?
While candidates will sometimes not want to weigh in on complex issues without knowing all the details, tell them you’re not looking for perfection. If they still demur, thank them and move on. You should get two or three concrete ideas or examples of how they’ve solved similar problems when you interview an executive. Anything less means they aren’t ready to contribute at the required level. After all, that’s what they’ll need to do once they’re on the job.
If you get evasive answers or long-winded unrelated stories, this should be considered a flag. Maybe they’re nervous, or they didn’t understand the question or they’re BS-ing their way through the interview. None of these are positive signs.
Also beware of candidates who regurgitate what they’ve picked up on in meetings with other people. Executives need to weigh in with well-thought through opinions. It can’t be a surface level discussion.
Executive Skills
At the executive level, you also need executives who can provide leadership in difficult situations. You never have perfect information and there are always trade-offs to be made. Your VP of Engineering needs to know how to balance tradeoffs between innovative new features and maintenance, between big customers and small, and between corner cases and mainstream.
They also have to be comfortable weighing in on tough issues around security, reliability and know when you’re taking on too much risk or making technical decisions that might come back to haunt you.
Remember, shipping is a feature! At the end of the day, you want to make sure your VP of Engineering is able to lead teams to get stuff out the door.
No VP of Engineering will tick all the boxes and so when you make tradeoffs, remember that the primary role of the VP of Engineering is internal. Their job is to ship great software. They might not have the charisma or polish that you have in other areas (especially compared to Sales.) But it’s better to have quiet leader who can ship than a public figure who can’t.
If over time you find your head of engineering is a better external figure than internal, that’s fine. Perhaps you can make them Field CTO or some other externally facing role. But you still need a strong internal leader who can make sure the trains are running on schedule.
The Best of the Best
The best engineering leaders I’ve worked with were all remarkably different in their personalities. Some were overbearing, some understated, some quirky, some polished. But they shared certain key attributes:
They were hands-on
They were low-ego problem solvers
They cared about customers
They made tough decisions
They were comfortable translating the needs of the business into technology
They challenged the teams that worked for them to do great things.
They developed the next generation of leaders
The leaders I’ve seen fail, did so because they weren’t hands-on, they couldn’t make decisions or they couldn’t back down from their own technical biases.
When a strong leader joins the organization, you feel the impact within 30-45 days. There should be an obvious and positive energy emanating from the team. Complex decisions that paralyzed teams get resolved. People might not agree with every decision, but productivity and morale both go up when people are focused on the right things.
Thank you to several excellent VPs of Engineering who contributed to this post.