Crossing the chasm: from operator to 10 Years at Up
By James Burrows, Managing Partner, The Up Group
A little over 10 years ago, I was asked a question that changed the direction of my career.
Clare, Up's Founder and CEO, uttered the now fateful words "Have you ever considered a career in search?"
I hadn't. I was an operator, a builder. I'd spent the previous 15 years building businesses, raising money, scaling revenue teams, entering new countries and regions, and navigating the highs and lows that come with working inside 24/7 fast-growth, VC- and PE-backed companies in Europe and USA. Search felt like a different world entirely.
But the more I sat with the question, the more it made sense.
Where I came from
My career started in the world of media and advertising — on the creative side of multi-national ad agencies like JWT, Publicis and what was RKCR at the time — where I developed a genuine passion for brands, and the commercial dynamics that sit behind them. It was both a lot of fun and an exceptional period of learning, but my instinct was always to be closer to the product, the revenue line, the growth challenge, and most importantly the people that wanted to also build companies.
In 2000, I made the leap. I co-founded Espotting, which grew to become Europe's largest pay-per-click business (and luckily before Google had launched AdWords). Over five years, we raised over $20m from seed through to Series C, built teams across eight countries in Europe, and eventually sold the business to a US competitor who wanted the number one player in Europe. It was an extraordinary ride, and one that taught me more about leadership, hiring, and organisational dynamics than anything I'd encountered before. I lead a team of 150+ with zero management experience (for which I apologise profusely to each and every one of them). Crucially, it also taught me how much the wrong hires can set a business back.
What followed was a series of senior operator roles — CEO, CCO and CRO — across early-stage and PE-backed businesses in London and New York, all going through periods of rapid growth. The same fundamental challenge kept coming up: getting the right leaders in the right seats at the right moment of the journey.
Why search — and why Up
When Clare asked me that question in 2016, I recognised something in Up that I hadn't seen elsewhere. This wasn't a firm that treated leadership hiring as a transactional process. It was one built on judgement, long-term relationships, and a genuine understanding of what organisations actually need at different stages of growth.
That last part mattered most to me. Because having sat in the rooms where those decisions get made - having been a co-founder sweating over a CRO hire, or the CEO working out what kind of commercial leader the business needed to scale into a new market - I knew how much was riding on getting it right. I also knew how rarely the person helping you had ever felt that weight themselves.
That's the operator advantage. Not just pattern recognition across industries and growth stages, though that's real and valuable. It's the ability to sit with a founder or a board and understand the decision they're actually facing — not just the brief they've written, but the anxiety behind it, the trade-offs they haven't articulated yet, the difference between what they think they need and what will actually move the business forward.
Ten years on
A decade in, my team and I specialise across B2B, with expertise across the core sub-sectors within Software/SaaS, FinTech, AI, Media & Advertising and also building leadership teams for PE and VC funds - I still think of every search as the kind of problem I used to have to solve from the other side.
One thing I've noticed over the past few years is how durable this kind of work is. As AI reshapes workflows, organisational design, industries and our economies, the ability to read people, understand organisations, and exercise human judgement becomes even more valuable.
A final thought
Across my entire career so far, I regularly re-calibrated my views on what gets me up in the morning and gives me energy - and the answer is people. Being a connector, being curious about what makes people tick, understanding what they get out of bed for and building long-term relationships with people I actually know and understand.
So, if you've had a career as an operator and found yourself wondering whether there's a different kind of challenge out there, we'd love to talk to you.
We're actively looking to bring more operators into Up. People who've built things, led teams, sat in the uncomfortable chair. People who are curious about other people and drawn to the strategic side of organisational growth. People who are nervous to try something new altogether by stretching themselves into the (un)comfort zone, and have the commitment, desire and mindset to do what it takes to make it work.
One of the best things that has ever happened to me is being asked that question. So if you're curious, I’d be very happy to pass on the favour.
Get in touch with James at [email protected] or connect on LinkedIn