A Sign of Progress

I just wrapped my thirteenth quarter at Teleport.

I still remember the days of walking into a tiny office with a mini-fridge and chasing down mini-deals. I grinned from ear to ear the first time our CEO gave me a shoutout in Slack. It might’ve been a $12k deal, but I felt like a million bucks.

A couple of quarters in, we weren’t growing fast enough to grab the attention of top-tier VCs. But, our customers loved the product, and we were building with sheer intensity. Over several quarters we steadily improved every aspect of our game. Finally, in mid-2020, the momentum was palpable. Suddenly, the most recognizable cloud companies were paying $100k+ for our software and expanding their usage.

Hiring also became easier. In the pre-traction days, one of the first managers I hired quit after his first week. His tenure was shorter than the hiring process. A-players were now asking if we had any roles available after receiving a rejection email. They just wanted a seat on the rocketship.

After a successful rebrand, we started posting our best numbers quarter after quarter and grew the revenue team to 70+. We were suddenly cool. At least, according to Gartner.

I didn’t think things could get any better. Our reps were making money, and we were hitting all of our numbers. So I was taken aback when our CEO told me it was time for us to start looking for a CRO aka my new boss. I still remember asking him, “why?” I don’t remember what his answer was. There was too much adrenaline and uncertainty to filter through. I was plagued with questions like:

What if they bring in a CRO who blows things up and kills the culture?

Am I even going to be allowed in board meetings anymore?

I felt like things couldn’t be going any better on the revenue team, and “if it ain’t broke, don’t fix it,” right?

The truth is my initial reaction was purely ego-driven. Virtually every aspect of our sales function could be improved. You can always be growing faster. After all, 3x YoY growth is table-stakes in this game, and companies like Deel are going from $5 to $50 Million ARR in one year.

I started feeling a lot better about the CRO search after I had some time to digest it. Here’s what I knew for sure:

  • The founders at Teleport always had my back. They genuinely cared, and always acted in the best interest of their employees.

  • I could learn a lot from a CRO. Up to this point, all of my learning was “on-the-job,” and working with a more experienced leader would help me grow.

  • Our executive team was relatively inexperienced for our stage, and since Teleport was my first time building + scaling a hyper-growth startup, we would benefit from a more seasoned sales leader on board, especially when raising our next round.

I could either help our CEO recruit our CRO or sit there sulking about the fact that I didn’t get to be the next Chris Degnan.

When I decided to get involved in the recruitment process, I knew exactly who to reach out to. This person had been my most valuable mentor over the last couple of years and was always willing to hop on a call to discuss things like territory planning and comp structures. I figured it would be a long shot since he was already running a sales team, but I went for it anyway.

Our texts quickly escalated to Zoom interviews, culminating in a presentation that sealed the deal.

I couldn’t be more excited to build the next phase of Teleport with our new CRO. But, what I’m most thrilled about is the ability to play good cop, bad cop with him when we start rolling out changes some AE’s will surely dislike. Like increasing quotas.

“Don’t get upset at me folks. This is all coming from our new CRO.” 🙂

In all seriousness, next time your boss says it’s time to hire someone with more experience than you, don’t assume you’ve done something wrong. View it as a sign of progress and acknowledge there’s always room for improvement.  Focus on what’s best for your team and don’t succumb to ego-driven thoughts like needing to have the fanciest title. What got you this far is a commitment to building a great company. Having a new leader on your team shouldn’t change that. In fact, it can increase your chances of doing so. It’s time to adapt and commit to setting up your new leader for success. If you do it right, and your heart is in the right place, there’s no telling how far you can go together.

It’s time to build the next phase of the company.