Want to be a startup’s first business hire?

First business hires at a startup are stem cells. Typically, a startup gets to 3–10 engineers before they look for their first GTM role. And for good reasons:

1. Founder-led sales & customer success is not just effective, it’s essential. Founders (typically CEOs) need to hear from prospects directly, and early adopters love co-creating with founders, not be sold to.
2. There’s no playbook yet. This makes it hard to define a clear role you can jump into and be effective at.
3. The product may not be ready yet. You’ll want to ensure that the team can actually do more with a GTM hire, and you won’t feel frustrated waiting.

However, after their first few customers, B2B startup CEOs need leverage. While every startup’s needs are differently split across sales, marketing and customer success, CEOs are essentially looking to hire their right hands.

They will mostly view you through the lens of: “can you make me more productive?”

“Why should I care about startups?”

There’s a very timely discussion with Amplitude founder Spenser Skates sparked by their recent IPO on early hires. The classic startups vs big tech post is here. TL;DR: Startups are one of the fastest ways of accumulating career capital.

I have lived this, as employee # 5 at Instabase, and seeing it grow from no customers to a $xB valuation. I got some invaluable lessons along the way, and some street cred to boot.

“What are startups looking for?”

Of course there’s variability here, but some common traits founders like:

1. Jack of all trades. Sometimes, you’ll have 1–2 primary responsibilities but almost always you’ll be doing something you hadn’t done before.
2. Execution and creativity. Speed is a startup’s biggest advantage, and they’re looking for hustlers that can do more with less.
3. Can-do attitude. A startup is a place for mostly-optimists, or realists that figure out how to punch through walls.
4. Independence. You won’t have 6 months to ramp up, and while you’ll get support you will get far less direction than you’re used to.

“How should I evaluate startups?”

Use your own judgement, here’s how I approached my decision.

Think like an investor. Time is your most valuable asset, so you want to make sure you’re investing well. Think about:

1. Strength of the founders and founder-market fit.
2. What does success look like for the company?
3. What are the biggest existential risks?
4. What is the growth trajectory so far?

Think about how well you are aligned.

1. Do you believe in the narrative and the vision?
2. Will the role allow you to explore or exploit your natural strengths?
3. Will the culture allow you to thrive?
4. Are you comfortable with their current runway and your compensation package?

“I think I want to join xyz. How can I ensure success?”

1. Do you have a 30–60–90 day plan for me? Here’s ours, for example. I highly recommend you get clarity here. It’s less about a role/title and more about ensuring the company knows what you will be responsible for and that you can prove it to them.
2. What is the level of seniority expected? Most early startup roles have a mix of strategy and execution. You should align on whether you’re going to come in and make x hires or if the startup is expecting you to do the work yourself for 6–12 months. This is an underrated failure mode I’ve seen at every job I’ve had.
3. How will I be supported? Since your job will likely need you to do more than you have previous experience with, you should ask about the best ways to get yourself that support. Mentorship, training and even the right tools can go a long way.
4. If it doesn’t work out in 6 months, why? This illuminates your biggest potential sources of failure, and gives you a prioritized list of what to iron out first.

LogicLoop is looking for our first business hire! I made this guide to share with candidates, and if you have a friend looking to join a startup, share it with them.

Feel free to email me at hi@getlogicloop.com if you want to talk about startups, data and operations.