Accelerate Your Path to VPE: Join a Series A Startup

If you’re an engineer looking for larger impact you might have your eyes on an engineering leadership role at a Series A startup. During my seven years as VP on Sequoia’s Human Capital team, I’ve helped dozens of early-stage companies hire their first engineering leader — which means I’ve seen dozens of candidates take risks on Series A roles with a lot of success. I’ve also seen a lot of aspiring VPEs held back from their dream job because they don’t understand the thought process of founders, employees and investors.

This post will take you through two efficient pathways to grow your career from engineering leader to VPE.

Lead the Team of Tomorrow

For a founding team, finding the first engineering leader can be a make-or-break moment. They’ve achieved product market fit, and finally have the funding they need to pursue their goals. Hiring the right person to lead the engineering team through this next phase of growth often makes all the difference for de-risking the company’s future.

Unlike a large organization with a robust engineering leadership structure, a startup only has one chance to get it right. The engineering team will heavily judge the founder’s decision-making abilities based on this one critical leadership hire. Because the stakes are high, few founders are willing to take a bet on an engineering leader who doesn’t have the right track record. They might not say it outright, but the truth is, a Series A company doesn’t need a leader for today’s team. They need someone with proven experience leading a team that’s much larger — the size they hope to be in two years.

How to Gain the Experience You Need

For engineering leaders who already have experience leading a team of 20–40+ people, considering a role leading a team of ~10 might feel like a large step backward. I’d argue that one step back could lead to many steps forward, as the company doubles or triples in size over the next few years. Your guidance through that major inflection point will unlock larger roles with higher-profile startups as you progress in your career. Even then, you are likely to take a step back at some future point, in order to push forward — the cycle continues.

In other words, the career trajectory of a successful VPE — from intern to public company CTO — isn’t linear. You will need to be vigilant to avoid plateaus and you will need to have the courage to take the risks that will help you reach your greater goals.

Path 1: From Tiny Startup to Microsoft

Take one of my favorite examples, Kevin Scott. In 2007, after working as a Senior Engineering Manager at Google for four years, Kevin took a VPE role at a then-tiny startup called AdMob, a role he actively pursued by cold emailing the CEO. Over the next three years, he led the team that built the platform into one of the top mobile advertising networks — and Google’s then third-largest acquisition at $750M. After a second stint at Google, this time as Senior Engineering Director, Kevin became a Senior VPE at a then mid-stage LinkedIn, overseeing all technology, including engineering, operations, IT and security. Shortly after Microsoft acquired LinkedIn in 2016, they promoted Kevin to CTO and he’s held that position since.

If Kevin had stayed at Google, his odds of moving up the ranks from engineer to CTO would have been close to zero. By leaving the security of a large engineering organization for the relative risk of a small, early-stage startup, Kevin proved his ability to grow and lead a team through pivotal inflection points — and earned the opportunity to run engineering at one of the largest and most influential tech companies in the world.

Of course, not every startup will achieve the success that AdMob found and not everyone is Kevin Scott. For most technical leaders, the path to a role like Kevin’s will include multiple “Head of” and VPE roles at small and medium companies that never make it big. But each of those experiences will make you a better leader if you are focused on learning and improving your craft. Think of yourself as a touring musician, building your skills in small venues as you prepare for stardom. You’re never guaranteed a big break, but the more shows you play and the tighter your set, the more likely you are to be discovered as an “overnight” sensation. If you position yourself well, you could have three or four opportunities to lead a growing engineering team at a company with a real chance of commercial success — and to find one that eventually breaks through.

Path 2: Stay the Course or Jump to High-growth?

In 2014 I had a conversation with a great Engineering Director for a then-pre-IPO company. She was excited about her current role but was eager to play on a larger stage as “the” VPE at the next big company, so she asked me to connect her with potential opportunities. She had many of the qualities that our portfolio companies value in technical and people leadership, but she was only considering companies with engineering orgs nearly double the size of her current 20-person team. We had a great discussion and I shared that she would certainly be considered for a VPE role in many companies, but likely not at the caliber of company she had her mind set on. The higher the profile of the startup, the greater risk aversion the founders will have to an unproven leader. In most cases, like this one, it wasn’t a matter of ability holding her back, it was a lack of demonstrated success at that next level of growth.

To help her reach her goals, I suggested two paths: she could join a small startup looking to double or triple in size, or she could stay the course at her rapidly scaling company and acquire the bonafides she needed to reach the next level. Both are valid, with benefits and tradeoffs. Her current role was a faster path to demonstrating larger team management skills. At a small company, an engineering leader might spend years hiring 30 engineers — or never get there at all if the business falters. Whereas a high-growth company could shift 30 existing engineers under that same leader in 1–3 months. On the other hand, if she chose an early smaller startup, she would gain valuable experience learning how to personally recruit without the safety-net of a big brand, how to motivate and level her emerging org without the assistance of formal HR, and she would almost certainly contribute directly at the C-level toward the company’s success. She chose to stay at her rapidly scaling company and, two years later, was promoted to VP of Engineering.

Three Top Qualities of Exceptional Series A VPEs

Truly exceptional VPE candidates have more than just experience. Here are three top qualities Series A companies look for:

• Ability to control outcomes despite uncertainty. There’s no way around it; startup life is rarely predictable. Can you still deliver product reliably in this environment? Can you demonstrate good judgment under shifting conditions? Are you structured in your decision-making? Founders want to feel confident that you have a method that will help you succeed.
• Ability to grow a team. The team you’ll be growing and managing needs a leader who believes in them — and who can help them mitigate the risk of burnout. Are you able to make and back up personal commitments to career growth across the org?
• Ability to communicate well. The best VPEs have strong relationships with their colleagues in sales, marketing and product management. They understand needs across the organization and can translate those needs into engineering deliverables that will support business goals. They are good storytellers, helping the team understand the “why” behind a new or changing focus, and ensuring everyone feels connected to the company’s goals and understands their impact.

Making Your Case: Include a “Why” When You Interview

Even if you check every box for an exceptional Series A VPE, you won’t get far unless the founders recognize your qualifications. Many of the early/seed stage founders we work with have never interviewed a VPE before, so I recommend that candidates include a “why” with every answer. If someone asks if you’ve managed managers, for example, don’t just say yes and describe the project and the team size. Volunteer an explanation of why you built layers into your org and how you gave autonomy to those you led while still ensuring that product was reliably delivered. Share how you determined your objectives and how you met them. In other words, always look to give your potential colleagues a deeper understanding of how you think.

While a role as a startup’s first engineering leader can provide exciting opportunities, it’s not a job that will fall into your lap. You need to actively cultivate qualities and demonstrate experience solving issues at the next career level to ensure you are a founder’s surest bet.

If you’re interested in learning more about VPE roles within the Sequoia community please contact Theresa Lee.

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This blog post was originally published on LinkedIn and was inspired by a panel Bret Reckard participated in at the 2019 SFELC Summit.