What It Really Takes to Be a CIO in a PE-Backed Tech Business

Insights from Rob Hesmondhalgh, former CIO of Lineup Systems - a global media sales & revenue management software company, which delivered an 8x return on investment through a successful PE-backed exit.

In the latest episode of Diary of a CIO, our host Sarah Pawson sat down with Rob Hesmondhalgh, a seasoned CIO whose career spans everything from software engineering to strategic leadership at Siemens, and most recently as CIO at Lineup Systems through to a successful private equity exit. What followed was one of the most honest, practical conversations we've had on the show.

Here are the key takeaways.

1. The CIO Is a Business Role - Not Just a Technology Role

Rob's most emphatic point: if you're a CIO in an investor-backed tech company, your primary job is value creation, not keeping the lights on. Investors have clear commercial expectations, and as the most senior technology person in the business, that responsibility sits with you.

His advice? Get close to the numbers. Understand the P&L, cash flow, and how the business recognises revenue and cost. Spend time with finance, sales, and every team that drives commercial outcomes. And don't be afraid to say "I don't understand, can you explain it again?" That kind of intellectual humility, he argues, is a superpower at the top.

2. Leadership Is About Creating Momentum

You can't be everywhere at once. Rob's philosophy is that great leaders build enough momentum that the organisation moves in the right direction even when you're not in the room. That means:

• Communicating a clear and compelling vision, not just what you're trying to achieve, but why
• Helping every individual understand how their work connects to the bigger picture
• Maintaining honest, transparent communication with regular feedback on progress
• Trusting your team to make the right calls when you're not there

3. Working Towards Exit Requires a Different Gear

When a sale is on the horizon, the scrutiny on your technology estate increases dramatically. Buyers look hard at risk, technical debt, platform longevity, organisational dependencies, security posture. Rob describes building a structured 12-month plan, prioritised by risk and value, tracked at board level every single month.

The lesson: don't wait for a sale process to get your house in order. Every CIO should be running that kind of risk and value balancing act continuously - the PE environment just makes the stakes more visible.

4. Move Faster Than You Think You Can

"Don't let perfect be the enemy of progress" came up more than once. Rob's view is that teams often under-estimate how fast they can move and over-index on planning at the expense of doing. His advice: lock down the non-negotiables (security, data privacy, the fundamentals), then run at everything else as fast as possible. Make mistakes. Learn quickly. Keep moving.

5. Outsourcing Is Harder Than It Looks

One of Rob's candid reflections: Lineup tried to outsource development before they were truly ready for it, and paid the price. The relationship with an external development team is fundamentally different from an internal one, it demands crystal-clear articulation of outcomes, strong governance, and a very different style of delegation.

His recommendation: if you haven't done it before, seek advice from someone who has before you start, not after the first difficult quarter.

6. Work-Life Balance Requires Intentional Design

Remote and hybrid work removed the natural buffers that once separated work and home. Rob's answer was to build artificial ones: a Duolingo session before starting the day, blocking out lunch breaks company-wide at Lineup, physically stepping away from screens. For someone who genuinely loves technology and finds himself building agentic AI tools "just for fun" on a weekend, the discipline has to be intentional.

7. AI in 2026: Stop Thinking Tactically, Start Thinking Strategically

Rob's biggest challenge flag for CIOs right now: AI is delivering isolated, tactical wins - a slightly faster workflow here, a bit of saved time there - but those gains aren't showing up on the balance sheet. The shift that's needed is the same one that happened with digital transformation: map your entire value chain and ask where AI can play a structural role across it, end to end.

He also flagged a security risk that many businesses are sleepwalking into: employees routinely feeding commercially sensitive information into public LLMs without understanding that they may be losing control of that data. Education and clear policy are urgently needed.

8. The Cloud Isn't the Only Answer Anymore

The rush to move everything to the cloud has levelled off, and Rob expects the next few years to bring a more considered, hybrid approach to hosting, with some workloads staying in the cloud and others moving back in-house or into more localised infrastructure. Geopolitics, data sovereignty, and the enormous power demands of AI are all driving a fragmentation of where services will be hosted and consumed.

Watch the Full Episode

You can watch Rob's full episode and explore the rest of the Diary of a CIO series on our YouTube channel: Diary of a CIO — YouTube or see below! 

Diary of a CIO is a podcast by Fruition Group — candid conversations with C-Level technology leaders, exploring the journeys, challenges, and decisions behind the strategy. If you'd like to join us as a guest, get in touch with our marketing director at kat.mellor@fruitiongroup.com.