The wild story of how I was hired over 3 times at the company I helped start

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In September 2019, I joined a company’s founding team.

Over the following two years, we raised over $1 billion in venture capital.

The company grew to over 1,200 employees, all fully remote, distributed across over a hundred countries around the world.

We were named one of the “fastest-growing startups” in history.

During the heyday, we hired dozens of people every week.

Some weeks there were over 25 new hires. One week, 50 new hires were announced at our company all hands.

One of the mantras at the company was once you were hired, turn around and hire two of your friends. We simply couldn’t hire fast enough.

You were considered a veteran if you worked at the company for six months.

Having joined when it was just the founder and me, when we were pre-revenue, pre-funding, and pre-customers, I couldn’t believe this was happening.

Every day I had to pinch myself to make sure it was real.

It certainly was.

It became very real.

All hypergrowth stories have a dark side.

The first time I was hired over

I was first hired over in July 2020 right before we announced our Series A of $40 million. The company was about 60 people. An investor had joined our board but our founder managed to convince the person, who was a heavyweight GTM leader twice my age and had way more experience scaling startups and building GTM organizations than me, to join full-time as Chief Business Officer.

My role shifted to head of marketing.

I ran the marketing team until we reached 11 people.

In March 2021, we announced our Series C of $400 million. We had reached 410 people working at the company and we were still growing fast. But I was told I would not become Chief Marketing Officer.

The second time I was hired over

When the CMO was hired, I moved over to replace the head of marketing at a company we had acquired. This company’s marketing team was five people. It lasted for a few months before I was moved to focus on a new project - launching the first enterprise offering of the software.

In November 2021, I came back from family leave and had a choice. I could either stay working where I was or join a new team (another acquisition) that was getting ready to launch a new video conferencing webinar product.

However, this new business unit already had a head of marketing, so it would mean I would need to go another layer down and report to this person.

The third time I was hired over

I chose the role where I believed my skills would best impact the overall business, which meant joining the new business unit and getting hired over for the third time.

I specialize in launching new pre-product-market fit products and it was clear the team was going to need help in this area.

So there I am. A far cry from where I started. I was just a cog in the machine at that point, but at least I enjoyed the people I got to work with (most of the time), I was learning a lot, and gaining a ton of GTM experience. Plus, it didn’t hurt that I still had a large number of stock options.

Meanwhile, the marketing team under the CMO expanded to 45 people as the company reached over 1,000 team members.

I kept my head down and did my best work. I decided I didn’t need to be a “leader.” I didn’t need the recognition. I became the Wolf. I filled gaps, operated more in the background, and let my results speak for themselves.

Six months later, everything changed.

Then the CEO calls me

In May 2022, the CEO called me on a Saturday. We had an hour-long, very candid conversation.

He said a lot of nice words about my work at the company over the years. He told me a massive restructuring of the company is coming. He asked me if would be interested in running marketing across all the products. He also asked if I would run PR again, as serious changes were coming ahead and he would need my help navigating the choppy waters.

I said yes.

Over the next 12 months, the company underwent three rounds of lay offs. The CBO, CMO, and the entire marketing team were cut, as well as hundreds of others.

The rocketship turned into a rollercoaster. Fortunately, most of these former teammates have landed on their feet in great roles at stable companies.

During all this, I was promoted to VP Multiproduct Growth, above my boss. I was grateful and glad to have more influence in the company again.

Through all of this, I easily learned more in two years than what most people learn in 10 years.

I made some hard choices. I lived on stress. I ate a decade’s worth of humble pie and became painfully aware of my weaknesses over and over again.

But I chose to grind it out, operated in my strengths, and made the biggest impact on the business I could, while absorbing many lessons and a ton of experience and connections.

What I’d say to anyone in a similar position

At a hypergrowth startup, it’s really easy to get hired over. If you find yourself in a similar position, this is what I would tell you, based on my experience:

• Don’t take it personally. It stings to get hired over. It feels like you’re being pinned with an official, public badge of corporate inadequacy. Well, it’s not your fault. A 10-person company is different from a 50-person company, which is different from a 150-person company, a 500-person company, a 1,000-person company and so on. Getting hired over at a hypergrowth startup is not in your control (unless you’re a cofounder, but that’s another story). Just because you don’t hyper-scale with the company doesn’t mean you’re not valuable to the company. Find the role where you can make the most impact and just focus on doing good work. If you’re still not happy, don’t be afraid to move on. Do what’s best for you.

• Accept that this one isn’t the home run. The experience you’re getting, or will get, will serve you even more down the road, either at the same company or at your next company. You’re probably in the beginning or middle of your career. You’ll have more at-bats, even if this one doesn’t work out like you hoped. Your experience will be invaluable and you’ll have the awareness to better shape your role for a maximized outcome next time.

• Be very involved in the hiring of your boss. See it as an opportunity to learn from someone you look up to. Hire your mentor and study them. Don’t be defensive or antagonistic. Embrace their leadership and let it rub off on you. So when the decision is made that you won’t get the job, roll up your sleeves and help the team choose someone you want to work for.

There’s a lot more to say on this, and I plan to write more about my experience at this company, but I’ll have to leave it for a future newsletter.

If anyone has questions or wants to talk more about this, I’m open - send me an email or DM me on Twitter.

All the best,

Dave

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