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Daniel Doubrovkine

aka dB., CTO at artsy.net, fun at playplay.io, NYC

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I recently wrote about dividing CTO and VP of Engineering responsibilities. That post is only useful if you actually have a VP of Engineering. So how does one hire such an animal? Is the process different from hiring any other team member?

What’s Different?

While much of the hiring process remains the same, a VP hire differs from hiring individual contributors, leads or managers in some important ways.

  • The price of getting this hire wrong is higher, because a VP of Engineering inherits the entire Engineering team and can have an out-sized impact on breaking things that work well.
  • The hiring process is more demanding, because it engages folks across all of Engineering and across the entire company.
  • Executive support is more critical, because the budget ask can easily be twice one of a senior individual contributor.

Get Executive Alignment

You must prepare a strong case for hiring any VP-level role. The size of the team may be a good trigger, but a demonstrated need for upgrading management bandwidth is better.

In my case the team was put under significant pressure in 2018, having been reorganized completely around e-commerce goals. A director, who has been with the company from the very beginning, left a few months earlier, along with a couple of other key team members. New managers were hired or promoted and required increased support. Engagement started showing a decline for the first time in many years, as measured by a quarterly survey.

Get Comp Right

Agree on the total compensation target and any recruiting budget or fees with your CFO.

Discuss compensation with any external recruiter, and make sure they believe these numbers are reasonably within market range. Listen carefully when experienced executive recruiters say the numbers are too low, and go back to finance, if necessary, until you feel confident the budget allows for a VP-level hire.

Ongoing Communication

Over-index on communicating about each step of the process.

The Engineering organization and the company Leadership team both have a lot of skin in the hiring of another VP.

At Artsy I provided a tweet-sized status in the company Leadership Team meeting, the Engineering Directors and the Engineering Managers weekly, as well as at the team weekly stand-up as soon as the headcount had been approved. This included all important milestones, from picking and contracting an external recruiting firm to closing a candidate.

Communication with candidates is equally critical. Make sure to set expectations about next steps clearly, do what you say, say what you do. Always have a date for when you are talking to the candidate next and put it on the calendar.

I don’t like to exchange cell phone numbers with an Engineering candidate, and prefer to conduct business over asynchronous communication in e-mail. Texting is the equivalent of pager duty.

Writing a Job Description

Invest time in a great job description.

VP-level job descriptions are often dismissed by candidates as a mere formality, but can become a competitive advantage at the top of the recruiting funnel when well articulated. I prefer a job description that focuses on experience of building and shipping software, managing people and leadership.

At Artsy we sought an individual who earned their Engineering credibility through hands on work.

You are an experienced people manager, team leader, and a practicing full stack software engineer. You have held multiple senior leadership positions, including at least one of Head of Engineering, VP of Engineering or CTO with several managers of managers reporting directly to you. You are fully committed to enabling people to do their best work. You have an impressive track record of leading teams that built complex distributed systems, and you also continue and love coding at work and personal projects, time permitting.

We aimed at protecting and growing our uniquely open culture.

Throughout your career you have lead product engineering over multiple releases and shipped software with the help of an exceptionally strong team. You have created a culture of openness and collaboration across your organization and outside of the company through open-source work. You’re passionate about beautiful code and inspiring products and are looking for an opportunity to build something users love. You set an example for the entire team.

And we decided, ultimately, to concentrate the responsibility of achieving healthy velocity and growth within this critical role.

As Vice President of Engineering you will report to the company Chief Technology Officer and serve a team of Directors that lead product and infrastructure teams. You will be responsible for all software delivery, the Engineering team’s growth through hiring and internally, compensation and goal setting. You will recruit, support, inspire, and scale a culture of craftsmanship, innovation and commitment within Engineering. Together with your team you will make the right strategic decisions in the way we build software, and navigate the balance of delivering an amazing product, investing in the future and paying technical debt.

The job description spelled out responsibilities.

Directly manage several directors and help them enable their teams to do their best work.

Collaborate with the Product and Design organizations to ship software of exceptional quality.

Positively contribute to Artsy culture and represent its values.

Contribute to Artsy’s strong retention by cultivating a happy, motivated, and energized team.

Recognize great work and minimize tensions around mistakes or poor performance.

Source, screen, interview and hire talented Engineering Managers, Directors and Engineers.

Represent and advocate for the team in strategy, planning, product and design meetings.

Facilitate constructive collaboration between teammates, business executives and peers.

Work with multiple organizations to align priorities and build consensus.

Drive implementation of effective engineering processes and policies.

Represent Artsy Engineering and Management inside Artsy and outside in the industry.

Make time to contribute small amounts of code, especially in the open-source community.

And minimum requirements, none of which include such things as college degrees or years of experience.

Leadership of a large (at least 20, ideally 40+), growing team of engineers through several evolutions of > process and organization.

Demonstrated technical depth and significant experience in full stack, distributed systems.

Track record of outstanding people management, ability to influence and engage direct, indirect reports and > peers.

Exceptional written, oral, interpersonal, and presentation skills and an ability to interface with > executive-level management, board of directors, and staff.

Using a Recruiting Firm

Use an external recruiter, but do references on them.

Because of our open-source community engagement, Artsy enjoys a healthy rate of qualified inbound hires and has therefore never used a recruiter for Engineering. Unfortunately, VP-level candidates are often public roles and don’t usually apply online or visibly seek employment. Senior managers often only trust their closest friends with information pertaining to them leaving a current job, severely limiting networking reach. Finally, hiring a VP requires a lot of recruiting overhead and we were simply not equipped to handle it with a small HR team.

A recruiter will represent your brand. Artsy chose Riviera Partners to help us conduct the search and process. I can personally highly recommend them.

Pro tip: let the CFO or the COO negotiate the recruiter retainer and fees. Bad cop, good cop. They are also just better at it.

Hiring Process

It’s your responsibility as the hiring manager to own the candidate and to keep them engaged, and not HR’s.

At Artsy, half the executive-level candidates at the top of the funnel came from the team’s personal networks and the other half via the search firm. I had to make a list of “ideal” candidates and discuss various desired attributes with the recruiter.

External candidates engaged via a recruiter pitch, then were connected with me for an informational. Internal candidates first met with me, then were connected with the external firm.

The Informational

An informational with a VP-level candidate is typically a tour of the office, followed by a lunch or a long coffee. The goal is to get the individual excited about the opportunity, get acquainted with their future manager, to align expectations and get an early feel of what it would be like to work together.

Pro tip: you never get a chance to make a first impression, so make sure you don’t have a meeting directly following the informational. Having all the time in the world for the candidate signals overall low stress, general patience and thoughtfulness.

My informational often sounds like a sales pitch to most candidates, but it is also an actual interview. I spend at least 30 minutes before meeting anyone to go over their resume, read the recruiter’s material, research any externally available information, and prepare a list of questions to unearth potential red flags.

During these meetings I offer a deep dive into the company history and businesses. I deliver a map of the team structure, software, systems, engineering practices and articulate company values.

Speaking of red flags, I had rejected more than one VP candidate during the informational by simply saying that I don’t believe we have a good match, because ….

Follow-Up

Follow-up to an informational with an e-mail, thanking the candidate and outlining next steps.

Make it extra personal by highlighting what they said about the opportunity, attempting to underscore why this this job could be the absolute best choice for them.

I also like to include a handy and up-to-date GMail canned response that includes links to various topics I talk about during any informational. It’s a rabbit hole that will start you in the Artsy README and take you through some exciting company milestones to my personal blog.

Pro tip: while the next step is always meeting the CEO, move faster by also scheduling a first round of onsite interviews in parallel.

Onsite Interviews

I ensure that the candidate meets both their future direct reports and all members of the executive team by giving them a list of people and asking them to sort names and people functions in the order of their preference.

45-minute interviews are directed and focus on every aspect of the job description, ranging from technical ability to collaboration, scored against company values. At Artsy these are Art x Science, Openness, Positive Energy, Quality Worthy of Art and People are Paramount. All the data goes into Greenhouse. I also debrief any VP-level interview (where the interviewer is another VP) in-person.

The way Artsy interviews any Engineer is best described in this blog post, and it surely applies to VP of Engineering candidates.

References

The most accurate predictor of future job performance is past job performance, not how well someone can perform in an interview. Therefore references are used to calculate an NPS score for the candidate based on questions such as Please rank the candidate in your team and explain what separates them from #1.. The final hiring decision at the company is designed to be 50% one’s interview and 50% references and is ultimately made entirely by the hiring manager.

I typically ask the CEO and the internal recruiter to do at least one reference call, and take the rest.

Choosing a Candidate

Build a framework for choosing a candidate and write up answers to important questions using the feedback from the interviews and notes from references.

  • What are the candidate’s biggest strengths?
  • How does the candidate align with company values?
  • Why is the candidate a great fit for the company and the team in its current state?
  • What will the candidate bring to Engineering leadership?
  • What kind of manager is the candidate?
  • Will the candidate work well with people at the company?
  • Will the Engineering team work well with the candidate?
  • What will the candidate’s interaction with product collaborators look like?
  • Does the candidate have technical credibility?
  • How does the candidate understand and work with business?
  • Is the candidate customer focused?
  • Would the candidate be a good public voice for the Engineering brand?
  • Why did the candidate leave their previous job?
  • What are the cons and flags?

Share this document with everyone on the Engineering team, the Leadership team, other VPs and anyone who has had a chance to interact with the candidate. Ask for feedback and strong opinions.

Make a Decision

Ideally, all candidates have gone through the process together and arrive to the decision point at the same time. In practice this never happens, but occasionally more than one candidate is at the finish line.

Apartment hunting in New York exhibits similar scarce supply and high demand aspects as hiring a VP of Engineering. My broker has always advised to take the first great option and I have always followed that smart advice. Decide which candidate you want and reject everyone else in the final stages of the process. Do not pick one candidate and let another candidate hang in the final stages - a good candidate will easily sense that you are doing this, and that they are not the preferred hire. You will damage an important relationship and they will not take the job.

Tell the candidate in person or on the phone that you are making them an offer and why.

This is not a done deal. Pro tip: tell the candidate that you’re excited for the possibility or opportunity of working together. Everything can still go wrong from here.

Offer and Closing

Because you got alignment in the early stage of the process you already have compensation numbers at hand. Discuss these with the recruiter, involve the CFO and produce an offer.

Senior candidates will always want to understand the equity portion of the offer. From here the CFO should be available and make hiring your VP, their priority. The CFO is empowered to make quick decisions around equity and is typically an experienced negotiator. Let them do the negotiating, but watch out that the numbers fit within your compensation framework.

In the past I have seen runaway offers that literally “throw money” at the candidate until they accept. I don’t believe that is an effective strategy. I recommend not negotiating cash and having some flexibility in equity, including trading some equity for cash and vice-versa. Exercise restraint and never signal to a candidate that you are desperate to close them or that the company needs them more than they want to work at the company.

That said, sometimes the recruiter will signal that a candidate is willing to say yes to a specific compensation number, a sign on bonus, a relocation or equity package. Do everything within reason to be able to just say yes.

Congratulations

Congratulations, two and a half months from first intro to closing, you have a fantastic VP of Engineering!