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Point Nine Land

Finding Your VP of Engineering

Source: https://news.yale.edu/2017/02/10/grace-murray-hopper-1906-1992-legacy-innovation-and-service

Software is at the core of most high-growth venture-funded tech startups. Great software is built by great people, so the leader who attracts and manages those great people is foundational to any startup. A startup can’t be great without a great VP of Engineering.

Some startups are lucky enough to have a technical co-founder who has done the job or can grow into it, but most high-growth startups will at some point find themselves recruiting a VP of Engineering from outside of the company.

It’s not easy, but it can be done.

I’ve been a VP of Engineering (VPE) at several companies I founded as well as at a public company. I’ve been recruited as a VPE a few times, I’ve participated in hiring several VPEs, and I’ve participated in a couple of dozen other executive searches.

This post shares a few lessons learned from both sides of the VPE search, including how to get a great VP to join your company, what kind of candidate you should look for, how to evaluate candidates, and some common mistakes and pitfalls. Many of these would apply to any VP hire at a startup, and other are more specific to the Engineering leader, starting with the fact that:

Great Engineering VPs are in high demand

Most startups understand how important the VPE role is, so when they gear up to find their VPE, they focus on how they are going to evaluate candidates. They write a detailed job description, plan for a tough round of interviews, plus some role plays or hands-on exercises. And this makes sense: you want to find the right person, and the right person respects a tough recruiting process.

But evaluating candidates is only one piece of landing a great VPE. It would be sufficient if there were a line of candidates at your door who want the job and are eager to prove they deserve it, but this is almost never the case.

Engineering VPs are in high demand because of the sheer number of options they have. A great engineering manager can start their own company, join a tech giant like Facebook, consult, teach, or can join any one of dozens of other startups who are also also looking for their perfect VPE, like you are.

If a candidate is good enough for you to hire, many other companies would also like to hire her, so if you want a great VPE, you need to know why yours is the company she would choose.

This means you need to do a few things during the search:

  • Treat every candidate with respect, starting from the first phone screen. Imagine how you would treat an executive at a large customer who might buy your product — treat candidates with the same level of professionalism.
  • Don’t play games with titles — since you need a VP, give the position a “VP” title. Don’t hedge with a “Head of” title — it will make the position less attractive and will bring in a lower caliber of candidate. If you have some pre-existing issues with title equity inside of your company, resolve them before starting the search.
  • Never assume that the candidate wants the job — instead treat the interview process as a mutual exploration from both sides on whether the company is a fit for what the candidate is looking for. The first few discussions should feel like dating, where both sides are asking lots of exploratory questions.
  • Sell the candidate on your business throughout the process. Give a product demo, walk through your last fundraising pitch, give your first meeting pitch. Explain why your startup is a compelling opportunity, but also be very honest about the weaknesses and risks you have in your business — you are looking for a person who wants to help fix them.
  • Plan to have the candidate meet a broad set of people at your company, including the rest of the executive team and some of the key people in other departments. You’ll do a better job evaluating the candidate, and those discussions will help the candidate understand more about your team and if they are a cultural fit.
  • In the later stages of the process, plan to share some sensitive data: your financial and product plans, board meeting notes, cap table, fundraising pitches. Most savvy candidates won’t join a company without this level of disclosure. (Would you?)
  • Once you move to offer stage, get your board and investors involved in closing the candidate — she is going to want to hear why the investors invested and that they plan to support your startup in future financings. Helping close executive hires is one of the main reasons you have a board, and they enjoy being asked.

Generally, put yourself into the shoes of a great VPE and ask what information you’d need and what emotional reaction you’d need to have when meeting a startup to pick it over the alternatives. Design your recruiting process to accomplish exactly that.

Don’t “overfit” the job description

If you want to hire someone to do a job, it seems logical to seek someone who has done that job before.

If you are a software-as-a-service company selling a CRM product built on Microsoft Azure growing from $10M to $50M ARR and from 20 to 100 engineers, it’s tempting to write a job description for someone who …. has been a VP of Engineering at a CRM SaaS company built on Azure which grew to $50M ARR and 100 engineers.

This almost never works for two reasons:

The candidate pool
As discussed, great VPEs are already scarce and hard to find. Every time you add a precondition to the job description, you shrink the pool of candidates.

If there are 100 VPE candidates on the market in your locale right now, you want to be able to talk to a couple of dozen of them. You don’t want to add so many conditions to your search that only a handful (or even zero!) of those candidates satisfy the venn diagram of requirements you’ve laid out.

Career development
If you think about the most successful people you know, they have probably risen rapidly through their career, where each position built on the last but also let them take on new challenges.

This is who you want. Don’t ask someone to pause their career growth to join your company and repeat exactly the same job they last had. How many ambitious and talented people will sign up to spend the next five years of their life doing exactly what they did over the previous five? Would you?

This means that most candidates will come to you with a mix of things they know how to do and a mix of things they are doing for the first time. They’ll be attracted to your opportunity precisely because of the career growth represented by that list of things they are doing for the first time.

For example, the VPE you end hiring:

  • May not have been a VP before — perhaps they were an amazing Director of Engineering at a fast-growth company comparable to yours. Perhaps they were even better manager than the VP they worked for. The reason they’ll join you if that you give them the chance to run their own shop.
  • May work with a different technology stack — you want someone who understands how to build products like yours, but they may never have run a team building products on the exact same stack you are using. This usually is not a big deal — you are hiring a great people manager, not a Chief Architect, and tools and languages come and go.
  • May have come from a failed startup. Most people are going to learn more from a successful company than a failed one, but you might find a candidate who was an amazing performer at a startup that didn’t make it. They may arrive at your company extremely motivated to get a win on their resume and not make the same mistakes a second time.
  • May come from a different industry. You might find a candidate who has B2C experience but wants to join a B2B company like yours. Or someone who has worked on tools and platforms but not end-user applications. The reason they’ll join your company is that you offer the opportunity for them to learn something new.
  • May need to relocate — you can expand the pool of candidates by looking outside of your locale, especially if you are in a city where talent is scarce. You‘ll pay for relocation, and your VPE won’t have a local network of talent to draw on, but you might be able to get an amazing person to join if they want to move to your city. I spent a year in Barcelona, and recruiting then relocating VPs from startup hubs was a common recruiting tactic of startups there, since the local talent pool was small and Barcelona is a place that many people want to move to!

I’ve never been part of an executive search that found a candidate who was an exact match. Every search I’ve seen concludes by looking at the mix of things the candidate already has done vs. the things they’d be doing for the first time and asking if the tradeoffs work.

But a major caveat: this does not mean you should hire someone who feels like a compromise or where your team has a mixed or lukewarm reaction. You should feel great about the candidate despite the gaps in their experience, and you should feel like they are such a fast learner that the gaps are a minor risk.

Be clear where the position fits in the organization

With most executive hires, like VP of Sales or CFO, it’s straightforward to define where the role fits in the organization and what it owns. But some companies make the VPE role more complicated than it needs to be because of a few factors:

The technical co-founder
Often a technical co-founder was leading Engineering before the decision to hire a VPE from the outside. The company then scratches their heads about what that co-founder is going to do once the VPE arrives.

Some companies solve this by giving the co-founder the CTO title and then carving out a set of responsibilities for that co-founder. This might involve giving the CTO responsibility for certain architecture decisions, future products, or a component of the product.

This split of responsibilities is almost never an outcome of an honest assessment about how to build great products — it’s often a way to appease the co-founder or as a hedge against bringing in a VP. Don’t do it.

The VPE owns all aspects of building and shipping the product and should never have to get decisions approved by a CTO or split responsibility. If you decide you need a CTO, define the role to have no overlap with Engineering (or Product Management). The right solutions is often for the co-founder to join the engineering team as a senior engineer and report to the new VP of Engineering. That would in no way diminishes their status as a co-founder.

I was once involved in a VPE search for a SaaS company which is a now a public decacorn. The technical co-founder recognized the need to hire an experienced VPE but suggested a structure where all major engineering decisions would need to be “approved” by him given his co-founder status. Needless to say, that search went nowhere until they changed that

Product Management
In most cases, your VPE will be a peer to your VP of Product Management, so you need to hire a VPE who respects the role and knows how to work well with a Product Management team.

Ask candidates about their previous experiences with Product Managers, how they’ve built productive working relationships, and what processes they’ve used to collaborate across PM, Design, and Engineering. Be wary of candidates who have baggage and negativity towards Product Management.

You might find a candidate who wants to run both Engineering and Product Management. If you go down this path, be aware that there are very few leaders who can do both jobs well, and you should be honestly convinced that combining the groups is the right org structure for your company and not something you are doing to convince that VPE to join.

The VP of Engineering should report to the CEO: both the VPE and the CEO will be more effective, and most VPE candidates will steer clear of roles that do not report to the CEO.

Most of all, you should settle these decisions before you start to recruit so that you can write a compelling job description and not send mixed messages to candidates. If you have any internal disagreements on structure and role, solve them before you start to engage candidates.

An “impressive” resumes might not be impressive for you

You are going to take months to recruit this person, give them a large equity stake in your company, and the cost of getting it wrong is high, so it’s tempting to look for candidates with conventionally strong resumes, with items like:

  • Works at a top company like Google, Facebook, or Amazon.
  • Manages a large team.
  • Works on products that drive 10s of millions of revenue.
  • Works with cutting edge technology.
  • Degree from an impressive school.

These might seem like a can’t-lose proposition, but they can lead you seriously astray. It’s easy to find stories of startups who hired an executive who “looked great on paper” but turned out to be a total failure when transplanted into the startup.

The most basic principle of recruiting is this: you don’t hire a candidate to reward them for a job well done in their previous position. You hire them because you think they will excel at the job that you need done at your company. If you are a high-growth startup, this would be items like:

  • Growing a team — recruiting great engineers is the most important and most difficult part of the VPE job. It requires hours of Zoom calls and coffee shop conversations spent convincing great engineers to leave their stable job, take a pay cut, and join your startup. A manager from a larger company like Google may have never done this if they relied on internal transfers or tapping into the stream of new hires provided by the Recruiting department. It’s easier to convince someone to join Google than to convince someone not to join Google.
  • Product invention — startups don’t manage mature products in established markets. Most are struggling to find product/market fit, to hold onto it, and to rapidly innovate to stay ahead of the competitors. You need someone who enjoys shipping quickly and iterating, emphasizes agility, gives lot of decision-making authority to empowered product teams, and is willing to do the occasional unnatural act to win a big deal.
  • Constant change — every month is different at a startup. New team members, new products, more funding, more growth. You want a VPE who accepts the constant churn and change and does not have a bias towards keeping the team at a steady state. Most people claim they want a dynamic environment, but look carefully at your candidate’s background to see if that is truly the case. A startup can change more in a year than a big company might in ten years, and great startups VPEs enjoy that.

The earlier stage you are, the more you should bias your search towards candidates who have experience at high growth startups, where their time was spent solving the problems that your startup needs solved.

You might find an exception, where you find a great candidate who is tired of working at a large company and wants to jump into a startup career, but you should evaluate these candidates carefully. Do they really understand what startup success requires? Do they understand that most startups fail, and even the ones that succeed are often a mess? Do they understand which of their skills will and will not translate? Are they willing to take a pay cut?

One good rule is that a candidate should have already decided to join a startup at your stage before you try to recruit them. If you find yourself trying to close a candidate who is comparing your offer to an offer from Facebook, you are probably both wasting your time — that’s a person who hasn’t decided what they what to do with their life and should hit the pause button on their search until they do.

You are hiring an executive

Every executive job, including the VP of Engineering has two responsibilities:

  • Managing their function — including hiring the team, developing them, coaching or moving out underperformers, putting the right processes and structures in place, and executing like crazy.
  • Serving as a member of the the executive team — including strategic planning, helping the CEO, collaborating with the other executives, helping manage the board and investors, interfacing with key customers, participating in financings, and navigating an eventual acquisition or IPO.

Some startups make the mistake of assuming the VPE is going to spend their time hunkered down in the lab with the Engineers while the functions that are closer to revenue, like the VP of Sales or Marketing, will spend their time with the CEO, customers, and board. This isn’t the case, and you won‘t attract a good VPE if you don’t expect them to be part of the action.

When you interview potential VPEs, you should:

  • Have them meet your entire executive team.
  • Ask lots of questions about their working relationships with other executives in the past.
  • Evaluate their ability to contribute to the kind of strategic challenges that your company has.
  • Find out what they know about sales, marketing, finance, business development and, (especially) product management and design. They are not going to be experts in everything obviously, but they should have a healthy respect and curiosity for the other parts of the business.
  • Have a dinner, drinks, or other event with the executive team where you socialize with the candidate and get to know them out of the office.

As with any executive hire, you want someone who arrives at your company in the morning asking how they can help the company succeed. You don’t want someone who feels their role is to “advocate for Engineering” or to fight for as much budget as possible. Those are a big-company behaviors that hurt startups.

It’s going to be expensive

A VP hire can take several months and require dozens of hours of interviews from some of the busiest and most valuable people at your company. And it’s very common to get several months into a VP search, come close to making an offer to a candidate, having it fall through, then going back to square one and starting over.

Depending on your locale, you will probably want to use an executive recruiter to maximize your chance of finding the best candidate in the shortest amount of time. Rates vary by locale, and you should negotiate, but your reaction is going to be, “wow — that’s expensive!” It’s usually worth it.

You are going to pay this person a lot and give them a lot of equity. Get familiar with the market in your locale, and plan to make a healthy offer once you find a candidate who blows you away. Don’t overpay — you don’t want a mercenary candidate to join you just because you were the highest offer they received, but you also do not want to look for a discount VPE. You usually get what you pay for.

And remember that the cost of a bad executive hire is enormous — they can drive away some of your best people, bring in a set of mediocre hires that need to be replaced, and make bad decisions that spend months to unwind. A bad executive hire can literally kill a startup. Don’t rely on interviews alone when hiring a VP — they are unreliable. Plan to check up to 15–20 references of people who have worked with and for that person before, and make sure they rave about the candidate.

And of course, if after a few months of working with your new VPE, you realize you made a bad hire, waste no time asking that person to leave and starting the whole process over. It’s not that uncommon, and it’s way cheaper than the alternative.

Hang in there

Most of all, be aware that executive searches have ups and down. You’ll have moments where the pipeline is bare and it seems you’ll never find your dream VP. You’ll have moments where your dream candidate falls through. You’ll have moments when you are tempted to make an offer to a ‘meh’ candidate just to get the search over with. Don’t.

Hang in there — it’s a process, and it takes time, but great people are out there, and you’ll find one.

Good luck!



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Michael Wolfe

Michael Wolfe

Co-founder, Gladly. Advisor at Point Nine Capital. Five startups. Endurance athlete, SF dweller. Quora addict. Fanboy.