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Rory Underwood - from winger to Wingman

| Duncan & Toplis | 13 February 2023

Best known for being England’s record international rugby union try scorer and making 236 appearances for Leicester Tigers, Rory Underwood has since forged a successful career in business. 

He has over 20 years of experience working with businesses across a variety of sectors and he is the founder of Wingman, a performance consultancy business specialising in high-performance environments. Duncan & Toplis has worked with Wingman to provide support with bookkeeping and VAT for a number of years. 

A unique perspective on business

Rory is uniquely placed to talk about building a successful team thanks to his outstanding rugby career, his 18 years as an RAF fast jets pilot, and his experience running his own business. Rory said: 

“In some ways, it's easier in a sporting and a military context to clarify the target or the direction. You either want to win a game in rugby or hit a particular target for example in the RAF. When you’re a business you need to decide your goals, whether it is to hit your growth target or something else. Sometimes it's not clear. 

“In business, there are lots of people who have got a rough idea of their general direction, and a rough idea of what they have to do, but the link between the direction and what they do, isn't always there. So that in essence is what we're trying to provide at Wingman. 

“I've run and started two businesses, and I've spent the last 23 years talking to all types and shapes of businesses about high-performance environments. So I've got three strings to my bow now as an ex-rugby international, an ex-fast jet pilot, and now as a business consultant with nearly 25 years of experience.”

From winger to Wingman

Rugby union fans will remember Rory as one of England’s greatest-ever wingers throughout his distinguished career. As a player during rugby union’s amateur era, Rory’s day job involved a very different type of wing as a fast jets pilot for the Royal Air Force. 

After retiring from the air force, Rory set up a company with two colleagues from the forces. Staying with the company for 10 years, Rory decided to take the plunge and start his own business, Wingman, in 2008. He said: 

“The financial crash in 2008 put a real challenge on various things and it seemed like an opportune time to go on my own and spread my wings. I wanted to use that time to start small and grow, so I set up Wingman. 

“The biggest impediment to businesses creating high-performance environments is that they often have a nice strategy, but they don’t always know how to implement it. 

“Fundamentally what we're trying to look at is how to create clarity and simplicity of language and communication of business priorities, as well as cross-functional relationships and collaborative ways of working. That is what creates a high-performance environment. So that's what we do - we're a strategy consultancy and we enable organisations to deliver their strategies.”

A high-performance partnership

Duncan & Toplis and Wingman have been working together over the last few years, with Duncan & Toplis providing bookkeeping and VAT support for Rory’s business.

Talking about his relationship with Duncan & Toplis, Rory said: 

“I have known Duncan & Toplis for many years and when the time came to look for some additional financial support, it seemed a sensible thing to ask Duncan & Toplis.

“The people we deal with at Duncan & Toplis are both approachable and helpful. It was all set up really quickly and if there is an issue you can approach them and it gets sorted out. Overall, we have a great relationship with Duncan & Toplis and we are very happy with the way things are going.”

Before working with Duncan & Toplis, Wingman manually filled in a spreadsheet they’d send to their accountants. They wanted help to streamline their processes, and have someone on hand to ensure everything was being done correctly. 

To do this, Rory’s Duncan & Toplis adviser helped Wingman to get set up using accounting software Xero and the cashflow tool, Fluidly. 

Rory said: “The biggest thing a company or an owner should know is the numbers, but I was struggling to get my head around the difference between accounting and cash flow.

“Getting set up on Fluidly has allowed us to look forward 12 months to see what our cash flow is like, and to think more strategically and plan how we want to invest or pull the purse strings in - whatever needs to be done.”


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