Five questions with Lyndsey Simpson, founder of 55/Redefined

Every week, Ambition A.M. passes the pen (or keyboard) to those eager to share the unfiltered stories fuelling Britain’s entrepreneurial spirit.

This week, we spotlight Lyndsey Simpson, founder and chief executive of 55/Redefined, an employer-focused brand championing age diversity in the workplace.

Simpson founded 55/Redefined in 2021 when she found herself fed up with ‘ageism’ in the workplace – why was everyone so against age diversity? The mix of skill sets within generations might just be where the magic happens.

One of the nominees for Veuve Clicquot’s Bold Future Award, Simpson gives us a sneak peek into what she’s learned on her journey to changing the workplace.

Why did you start your business?

Back in 2018, I took a call from Natwest. My contact there was in a fix. They had to get a massive regulatory review underway quickly, and they needed bankers—from the 90s! At the time, I was running a large recruitment and HR outsourcing company, so I was in the business of solving HR headaches.

I still had my phone and contact book from my years as business development director at Barclays, so I went into private investigator mode and called everyone I knew from those days. In eight weeks, I had traced and hired 400 people out of retirement.

It gave me the spark of an idea to build an age-diverse jobs and talent marketplace for over-50s, which led to Jobs/Redefined being launched. And when I began researching data on our ageing population, changing human needs and the growing skills gap, I soon realised this was a massive opportunity – I was staring at a megatrend!

This led to our other two businesses, Life/Redefined and Work/Redefined, being launched to solve the gap in the market.

What is your biggest accomplishment (to date) as a female founder?

Walking into the boardrooms of some of the world’s largest corporations (where the majority of executives were men) and persuading them that not only were they missing out on older talent but that focussing on over-50s talent and consumers would actually give them a competitive advantage in the long-term, future-proofing their businesses.

I then had the satisfaction of seeing them completely change their business strategies as a result of our interventions.

What do you hope to achieve next?

I want to create solutions that serve the needs of real people and companies. So this year we’re launching a product that empowers people in midlife and helps them create a plan for this next new phase of working life, as well as solving a range of mission-critical issues that large companies targeting this demographic are experiencing.

My hope is that our new software-as-a-service (SaaS) solution will transport us into new international markets.

What is the biggest challenge you’ve faced?

It was 2008! I was a first-time entrepreneur at the recruitment firm The Curve Group when we hit a recession.

I quickly found that being brilliant at what you did, with a fabulous team and delighted customers, just wasn’t enough. In that tough climate, you can’t create markets. You just have to adapt and pivot quickly to the changing landscape.

The lessons I learned during that period made me a better leader and entrepreneur, and my business became stronger and more diverse. However, it was, without a doubt, the most challenging time of my career.

How do you define success?

Finding Ikigai. This is a Japanese concept where you combine what you’re good at with what you love, with what the world needs and with what you can be paid for.

I’ve been lucky that I have often experienced three out of four of these in my career, but now, I am in my Ikigai flow, with all four having big ticks and without ever having had to compromise.