Raising Engineers (eBook)

Introduction

Over the years, I’ve had hundreds of conversations with tech startup founders that sound something like this:

“I’ve recently raised some capital and now I need to hire engineers and build a team. How do I attract the right engineers and how do I ensure the team is productive?”

One of the most personally memorable of these conversations was in Austin, Texas in 2014. I met a founder in downtown Austin at a burger joint called Wholly Cow. He had been going around the country looking for other possible locations to expand his engineering team.

“We’ve recently raised $8 million. I’ve got five engineers and the funding to hire more, but growing the team has been a struggle,” the founder told me. “I’m currently flying around the United States meeting with engineering leaders trying to figure out if I need to build a team outside of San Francisco.”

I recognized his pain right away because I’d heard it from hundreds of founders before. Even with a sizable amount of cash available for hiring, putting together a software engineering team is not easy.

I started with the question I ask all founders: “What does your company do?”

His answer would change the next seven years of my life, all the way up to the present day.

“We create work-from-home jobs,” he said.

I knew instantly I wanted to be a part of that. For one thing, this founder already had in place the very first thing I tell founders they need to recruit engineers. He had a clear mission. He could’ve answered, “We sell speech-to-text services” or “We caption movies,” but he knew that was only what his company sold. Instead, he told me why his company existed.

When I heard it, I could instantly feel its power. Work-from-home jobs change people’s lives by allowing them to work where, when, and how they want.

Soon after that, I became the leader of the engineering team for this founder’s company, Rev.com. I’m still there and the mission keeps my motivational fire lit to this day. We’ve built a team that’s grown from a handful of engineers to more than a hundred, with about one-third of those engineers being MIT graduates. I’m pleased to say, this team has powered amazing growth at Rev and the company has gone from startup to success story.

All the key concepts I’ve learned to grow engineering teams at Rev and several other companies are in this book. And if you’re reading this, I’m guessing you know how that founder felt. You already know exactly how precious early investment dollars are. You also grasp that a high-performing engineering team is crucial to the success of a startup and are painfully aware of the flipside: a poor team can wreck a company.

The founders I talk to also typically have the following in common:

• They’re savvy and smart, and their companies have enough promise to have secured serious investment dollars.
• They have anywhere from one to five engineers on board already, and now they need to hire anywhere from five to twenty more (at least to start).
• This is their first time building an engineering team and they’re looking for advice they can trust.

If all this resonates with you, read on. You’ll learn both the high-level concepts plus the concrete strategies I’ve used to build high-performing engineering teams.

My Background in Startups

The super-brief version of my résumé would read something like this: 1995 MIT grad, then a couple of years as a software engineer, followed by leadership roles for more than two decades, including several VP of Engineering positions. But those are titles and roles, and what you care about is this: can you have confidence that what I tell you will help you build a high-performing engineering team?

I believe so. My twenty-five-plus-year career has been exclusively with startups.

One of the most formative experiences happened early in my career in the late 1990s at the now-legendary tech company Trilogy. Alumni from Trilogy have gone on to become founders at Carta, Capital Factory, Mozilla, and other successful companies.

Trilogy was one of the first tech companies to leave California for Austin. I don’t think it’s an exaggeration to say that Austin is a tech mecca today in large part because of Trilogy.

What made it special, however, was not that it was a pioneer in moving to Austin. The difference was in its commitment to building a special culture. Trilogy invested millions in hiring thousands of people who were the right fit for their organization.

I remember being flown to Austin for an interview. They put me on a boat and let me interact with their team. It was eye-opening to see how much people loved working there. It was infectious, and I recall thinking that this was definitely not the standard job hiring process, that the “interviews” were actually fun and gave a true window on what it was like to work there. (And this was the late 1990s, before other companies adopted Trilogy-like hiring strategies.)

Once I came on board, I loved Trilogy even more. No one told me I had to stay up all night and code, but I did it anyway. When you love your work and company that much, you’re happy to do it.

It was a special time, and no doubt some of it was because it was exciting to be young and at a company that was making such a big impact. But it was more than that to me. It also laid the foundation for my journey to discover how to create similar magic at other companies. In many ways, the heart of the ideas you’ll find in this book grew out of that one experience.

Of course, I’ve had many additional experiences since then. I’ve been in the trenches. I understand startup tech companies, and I understand the strategies and methods to help find and hire engineers who are the right fit. I’ve hired hundreds of engineers personally and advised on the hiring of thousands.

In my work with successful startups, I’ve met many of the top-name tech investors. So now after years and years of doing this, my core network includes fifty or so high-end investors who regularly put money into tech startups, and they repeatedly send founders to me for advice on building engineering teams. Through those connections, my view on raising engineering teams has expanded well beyond the startups I’ve been directly involved with.

Having experience specific to startups matters. There’s a somewhat common misunderstanding among founders that the best advice on building engineering teams would come from behemoths like Netflix or Facebook. It’s an understandable misconception because obviously these companies are extraordinarily successful. Why wouldn’t you want to follow the strategies of the biggest and most successful companies?

Setting aside whether you could find someone at one of these companies to advise you, the truth is, it wouldn’t be relevant to where you are now anyway. Huge tech companies are at a completely different stage of their life cycle, and their hiring and recruiting is a different beast altogether.

You need someone who can guide you from a small handful of engineers—maybe even only one—to the next five. And then the next five to ten after that, and so on. My advice is directly relevant to you because it’s been my life’s work to create high-performing engineering teams from scratch—and I’ve done it again and again. Of course, I’ve also made many mistakes along the way. I’ll also tell you what I’ve learned from my missteps so you can avoid them.

As you go through the book, I’ll share specific examples from my experience, particularly my most recent startup adventure at Rev.

I’ve also invested in several startups over the years, and this has given me even wider experience, connections, and contacts. Within the community of tech startups, particularly in Austin, this has snowballed into a reputation for building excellent engineering teams.

After talking with and advising literally hundreds of tech startup founders, I have a good handle on what works (and what doesn’t) for building strong teams. I’m sharing it all in this book.

What This Book Can Do for You

When you’re finished reading this book, you’ll know how to recruit and motivate a high-performing engineering team, and how to optimize your company culture and processes for maximum success.

As you go through this book, you’ll notice certain themes recur in many of the chapters. Two of the most important are implied in the title, Raising Engineers.

One of those ideas is that recruiting and hiring good engineers is only the beginning. Sometimes founders think that building a great team is mostly about hiring. That’s not enough. You also have to “raise” your team the right way. You need to find ways to give your engineers purpose, you need to give them some autonomy, and you’ve got to give them opportunities to master their craft.

Hiring does matter, of course, but if you don’t create a work environment where your engineering team is motivated, and if you don’t optimize the processes they work within, the best recruitment in the world won’t save you.

The other idea embedded in the title is the idea of caring. When parents do a good job of raising a family, it’s because they truly care and they show it. A thread that runs through this entire book is that you need to genuinely care about your team as people and look out for their best interests, too—not just your company’s.

Many of the founders I...