Top 7 Mistakes When Hiring Senior Executives for Early-Stage Startup

I've seen it happen too many times. A founder raises a nice seed round or big Series A and feels the pressure to "professionalize" the team, bring in people that “been there, done that before”...

I've seen it happen too many times. A founder raises a nice seed round or big Series A and feels the pressure to "professionalize" the team, bring in people that “been there, done that before” and rushes to hire a few senior managers / VPs. Six to twelve months later, they're all gone (and big portion of your seed funding is gone too).

Having been on both sides of this equation—bootstrapping to $1M ARR before raising capital and then scaling to multiple markets and crossing $5M in ARR —I've learned some painful lessons about bringing senior talent into early-stage companies.

Here are 7 mistakes you're probably making when hiring execs for your startup:

1. Being impressed by big company logos

Sometimes due to imposter syndrome, we become mesmerised by candidates with Big Co logos. It's an especially common trap, when you are a first time founder and never worked for a big tech company, then you might think “omg if they worked at Google/Uber/Facebook they really need to know how to grow tech business”.

It's typically a trap (or a gamble), because it's nearly impossible to identify who actually drove success at that company versus who was just along for the ride. There's a high chance you're recruiting a passenger, not a driver.

The person who "led growth at Google" might have simply been riding the wave of a monopoly business model. Their impressive LinkedIn profile doesn't tell you if they built the car or just enjoyed the view from the backseat.

2. Vague expectations and goals

I set up straightforward but detailed 30/60/90 day expectations plus quite a simple list of good/bad examples of behaviours/attitudes. This helps me evaluate these people after short periods of time, which is otherwise incredibly difficult in case of senior positions.

Without clear success metrics, you'll find yourself six months in wondering why that expensive hire hasn't "moved the needle" yet—and they'll be wondering why you're not happy with their "strategic thinking" and "foundational work."

3. The army they need to get anything done

Some senior folks can't accomplish anything on their own and need to hire ~5 people to deliver results. While this might be fine for you, make sure you know exactly who this person will need to actually get anything done.

This happens so often it's almost comical. Your shiny new CMO's first request is for a content marketing manager, performance marketer, brand designer, copywriter, and marketing ops specialist—before they've proven a single channel works for your business.

4. Pushing for big decisions too early

Since this is probably your highest-paid team member, I understand why you want to see your investment paying off quickly, but there's nothing worse than a newly joined exec making a catastrophic decision in the first month. It destroys trust and respect within the team.

Sometimes, it's impossible to recover after such a misstep in the early days. And it's remarkably easy to fail because they lack the company context needed to make sound judgments. Give them time to learn before they burn.

5. The "I want to get my hands dirty again" myth

"I've managed 100 people for the last 3 years, but I really want to play early-stage again and do work myself or manage a team of 3."

While this might sound genuine, I've never seen it actually work out. Once someone becomes accustomed to delegating everything, they rarely rediscover the joy of execution. Their muscle memory for doing the work themselves is very, very little.

6. For a person with a hammer, everything looks like a nail

If you bring in someone who managed a business where 90% of traffic came from paid channels, don't expect them to build a robust organic SEO strategy for your company. People typically clone what worked for them previously: "It's how we did it at XYZ". You will be really surprised, how much they stick to known territory.

Their playbook might be impressive, but if it doesn't match your market, timing, and business model (the holy trinity!), it's worthless.

7. Delegation vs. abdication

Delegation is not abdication. There's a ladder of delegation. Always start your relationship with a brand new direct report with the first level and never ever skip levels.

Make it explicitly clear that it's not micromanagement, but simply progressing through the delegation ladder appropriately. It's extremely difficult to move back to lower levels of delegation if you start too high.

Once you begin getting into details later (because you're unhappy with results), you'll inevitably be labeled a micromanager. Trust me on this one.

Happy hiring!