Lessons From My First 5 Years at a Tech Unicorn

Tech startups come in many forms: Bootstrapped, lifestyle, VC-backed, courting acquisition. And then there are unicorns – privately held tech companies that, through grit, luck, or magic, grow to be worth over $1 billion.

In my first five years at Outreach, it grew from a team of about 20 to more than 700. Taming a unicorn takes a unique approach. It’s not all rainbows, but if you push through, the experience will give you a whole new approach to business. Here’s a year by year breakdown of what I learned from my time working at one.

Year 1: Find your five

There is a saying that you are the amalgamated average of the five people you spend the most time with. That’s also true of the workplace. As the company scales, you’ll have a chance to work on many teams. I recommend it, especially if your goal is to run part of a SaaS company one day.

When I started at Outreach, I wanted the sexy title. After the first year, I realized it wasn’t about your role but the people you spent the most time with and what you learned from them. Start with a great boss, and you’ll likely end up around great people.

Your boss should be your internal champion. Seek out a great boss, and you’ll have someone fighting to get you whatever title you want.

Year 2: Hire the A+ generalist

In our second year, we were starting to scale. I’d sit in three to five interviews per week, and I learned a lot about hiring for a startup.

Looking back at many of the employees that did well, they all had a “get it done” attitude. Nothing was impossible, except for in engineering. To this day, these are the questions that guide what I look for in non-engineer hires.

• Do they have the motivation to tackle anything thrown at them?
• Can they bring others up with them?
• When others around them succeed, do they get jealous or are happy for them?
• Can they take a simple concept and execute on it?

What doesn’t matter is where they went to school, their major, their total years of experience, or their previous company. The A+ generalist will always win.

Year 3: Consider your inputs

I have an electrical engineering degree and studied signals and systems. Here’s a simple concept that stuck with me:

Input equals output.

If you input jerks, you output jerk culture. If you input only white, male, middle-class thinkers, you’ll struggle to get truly creative ideas out of them. But if you input great people, you’ll get great things.

The culture is the DNA of the company. It drives not only what you do but how you execute it. Let’s look at the 80/20 rule for culture – that who you choose to hire (while maybe only 20 percent of business decisions) impacts 80 percent of how well your company does.

I once asked Costco founder Jim Sinegal about his secret sauce. He said: “Hire good people, and they’ll do good things.”

Have you ever been to Costco and met a mean employee? Yeah, me neither. It’s surprising – considering they have to deal with people ramming carts into each other all day.

Jim’s tone made it sound like common sense. He didn’t even have to think about it.

Year 4: Unicorns don’t always live in rainbows

Most of what you see about Unicorn startups is the sexy stuff – funding announcements, Forbes and LinkedIn awards, famous hires, and Forrester Wave mentions.

Here’s the 1 percent you don’t hear about:

• Great friends and mentors will leave your company.
• You’ll have bad bosses as well as good.
• Poor hires will get through the door.
• Startups are still trying to figure it out.
• People will overthink a lot of business basics to sound smart.

You’ll see the same problems at a unicorn company as you see at any other company, and consistency is rare. People, processes, and rules have to change as a company grows. You can either complain about it or see through the changes as a team player. It’ll all be worth it!

Year 5: Have strong opinions, loosely held

We’ve hired Ivy League grads, PhDs, and “world-famous” award-winning people throughout the years. No one has all of the answers. We are all trying to figure it out, but that doesn’t mean you are indifferent.

Have an opinion, take a stance, and bring your perspective, but understand that what’s worked in the past may not work now. Instead, I learned to live in Unicorn Land by Paul Saffo’s adage: “Strong opinions, weakly held.”

This means you should have your opinions but treat them as hypotheses. With this mindset, you allow others the opportunity to prove you wrong as quickly as possible, overcome your own biases, and become more decisive because you’re building the muscle of making more decisions, more often. With this approach, we’ve built a diverse culture that creates a safe place for people to speak up—and you might, too.

Here’s the TL;DR:

1. Surround yourself with great people you can learn from.
2. Want to ensure a successful hire? Hire the A+ generalist.
3. Culture is 20 percent of the pie that will lead to 80 percent of your company’s success.
4. Understand that 99 percent of what you see online is the sexy stuff. Unicorns also have their problems.
5. Have strong opinions but hold them loosely.

With all this in mind, should you join a unicorn company? My answer is unequivocally yes, and this is why: You’ll be given more opportunities and can explore multiple career options. You’ll have a greater sense of accomplishment and resume bullets people dream of having. Working in Unicorn Land is like a mini MBA. Most importantly, you’ll learn how to build.