3 Insights on Leading a Start-Up Team 

Over the past seven years, I’ve been CEO of two different companies – AXDRAFT and AiSDR.

At both of them, I’ve had six main responsibilities:

• Leading the team and setting priorities
• Spearheading sales
• Building the foundation for customer success
• Providing an initial vision for marketing
• Keeping investors in the loop
• Making sure we had enough money in the bank 😀

And as each company grew in workload and customers, I took a step back from customer success and marketing to focus on leading, sales, and answering any tough questions that come our way.

Reflecting on my 2,555+ days of leading people at two start-ups, here are three things I’ve learned.

1. Culture works when you live and internalize it

At AiSDR, as well as at my first company, we strive to follow three core principles in our work:

During hiring interviews, I can approximate a person’s passion and energy by asking them three questions:

• What motivates them in life?
• Which achievement are they most proud of?
• When was the hardest they ever worked?

A person’s answers shed light on what really matters to that person.

Our leadership team tries to maintain a person’s passion and energy by trying to balance and shift workloads based on the person’s situation. 

If one of our teammates has an off day for some reason, we try to accommodate them while finding someone who can cover. We also do our best to match company needs with individual interests to create ways for people to pursue their passions.

To foster curiosity, each team member has to share “one thing I learned today” at our end-of-day report calls. Ideally, what they learned should relate to their primary responsibilities, but there’s no restriction on what they share so long as it’s new and personally interesting.

2. Cultural fit is a higher priority than skill set at start-ups

On a few different occasions, I’ve seen start-ups miss on a hire so badly that it ended up ruining the entire company.

Start-ups need a team that’s willing to come together and work towards a shared purpose, even if it means some long hours in the process. So when someone joins and starts asking questions like “Why do we have to work such long hours?” or “Why aren’t we paid more?”, things will turn sour pretty quick.

As a CEO of a start-up, there’s only so much you can do to control the situation. At my companies, I’ve done what I can to make sure my employees are well-compensated and that they don’t burn out.

It also happens that sometimes a person just doesn’t seem to mesh well with the rest of the team, even through no fault of their own.

Ultimately, early-stage start-ups are in a delicate position and need a team that’s willing to put in the time and effort. If you have people who detract more than they add, you’ll have to make the hard decision of letting them go.

3. Regular 1-on-1 meetings are critical early on

At both AiSDR and AXDRAFT, I’ve always tried to set up monthly 1:1s with my direct reports, as well as skip-level meetings at the end of the month.

I’m fortunate enough to be able to split meetings with my co-founder Oleg so that he covers half and I cover half. This way we don’t get spread too thin.

Without mincing words, monthly 1:1s can be challenging due to the time requirement, especially if you schedule them at the end of the month when you also have to handle accounting and investor updates. 

Once your team grows beyond 50 people, monthly 1:1s with everyone becomes effectively impossible.

Still, for early-stage start-ups, regular 1:1s is a good way to ensure your team is aligned, any misunderstandings get cleared up, and bottlenecks get removed.

There’s a reason I always call my 1:1s my secret to ultra-fast start-up growth.

Do whatever it takes to stay ‘default alive’

There were a lot of lessons I’ve taken and tried to absorb from my two experiences at Y Combinator. 

But one of the most impactful was the importance of staying default alive.

After all, start-ups regularly fail for many reasons, but so long as there’s money in the bank, you can keep your company alive and doing business.

Our goal at AiSDR is to help companies make growth easier and cheaper by automating sales and marketing with personalization at scale and no need for oversight.

If you want to explore how AiSDR can support your business, set up a time so we can discuss how to help.