Working in startups has taught me that hiring the right people isn’t about finding the most polished CV. It’s about finding people who can thrive when things are uncertain.
Priorities change weekly. Roles evolve faster than job descriptions. What mattered last quarter might be irrelevant by next. In this kind of environment, you can’t just hire for experience, you have to hire for adaptability, curiosity and initiative.
Our industry is well known for its thriving start up culture but recruiting for these fledgling businesses does come with challenges, the business - even though it is scaling fast doesn’t yet have a reputation or credentials candidates may seek comfort and job certainty in. But they also offer opportunity well beyond big, established players.
Startups don't need specialists. They need shapeshifters.
In a big company, roles are clearly defined. Everyone knows their lane. But in a startup, those lanes blur fast and that’s the beauty of it.
I look for what’s often called ‘T-shaped talent’. These are people with deep expertise in one area (the vertical part of the T) but enough breadth to stretch across others (the horizontal part). Maybe it’s a marketer who understands data, or an engineer who enjoys sitting in on customer interviews.
That mix of depth and flexibility means they can jump in wherever they’re needed, which is essential when you’re building something fast with a small team.
Technical skills are easy to assess. Curiosity isn’t, but it’s often what sets the great hires apart from the good ones.
Over the years, a few candidates have stood out because they didn’t just apply; they showed me how they thought. One made a short video about the value she could add to realestate.com, back when video applications were almost unheard of. It showed creativity, confidence and genuine passion for the brand.
Another documented her journey moving countries and how she used Rome2Rio for every leg of the trip. That insight told me two things: she was resourceful and she truly understood the product from a customer’s point of view.
Those examples stuck with me because they weren’t about experience. They were about mindset. These candidates found ways to demonstrate curiosity and initiative before they’d even joined the team.
Startups aren’t for everyone, and that’s okay. But I’ve learned to look out for candidates who rely too heavily on structure or hierarchy.
People coming from large, established organisations often struggle when the guardrails disappear. When I interview, I ask situational questions to see how candidates respond to ambiguity:
How do you handle conflicting priorities?
What do you do when you disagree with your manager?
Tell me about a time you had to make progress without clear direction
Their answers tell me a lot about how they’ll cope in a fast-moving environment. The people who thrive in startups don’t wait to be told what to do. They figure it out as they go.
If I had to give one piece of advice to someone joining a startup for the first time, it would be this: get involved.
The best people I’ve worked with are the ones who throw themselves in, ask questions and take the time to understand how the whole business works, not just their bit of it.
Startups are full of people who are open to explaining what they do. Even if you have no background in something like data or product, asking questions gives you a better appreciation for how it all connects. That curiosity is how you learn fast, not fail fast.
Experience helps, but adaptability wins. Startups grow because of people who are curious, creative and brave enough to take initiative before being asked.
The best hires don’t wait for the playbook, they help write it.
