55/Redefined Founder and CEO, Lyndsey Simpson (c) Veuve Clicquot
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Celebrating Our Founder and CEO, Lyndsey Simpson, Shortlisted for a Veuve Clicquot Bold Women Award

A heady morning in London surrounded by powerful peers, press and the unmistakable clink of champagne glasses, followed by a quick cab ride to pitch to the world’s biggest retailer. It’s par for the course for 55/Redefined’s Founder and CEO, Lyndsey Simpson.

For a woman who’s small in stature (she’s just 4’10”), Lyndsey Simpson is a force of nature who’s hard to ignore. Dogged determination, an unshakable belief in her quest and an inability to be told the word ‘no’ sets Lyndsey apart from her peers. In her forties, while our research tells us that many in her age cohort are considering flexible or part-time working, there’s no slowing down in sight for this powerhouse of a woman.

That’s one of the reasons why Lyndsey, along with four other remarkable women, were shortlisted for the Veuve Clicquot Bold Woman awards (Lyndsey is shortlisted for the Bold Future award celebrating entrepreneurship). The finalists were announced with a media morning in London in late February and a feature in Harpers Bazaar, no less. But the champagne had to be served ‘to go’, as she was on her way to do what she does best, and get senior business leaders to sit up, pay attention and recognise the value of hiring and retaining over-50s workers.

A New (Bold) Future

Since leaving the relative safety of paid employment in 2007 to become an entrepreneur, while it’s been a rollercoaster ride, Simpson wouldn’t change any of it.

The idea for 55/Redefined came about while she was running a talent business. Her clients were struggling to find more experienced talent and usual recruitment channels weren’t working. The discrimination faced by the over-50s was stark, and in sharp contrast to the inclusion agendas of the business world. Simpson set about to change that, and, in 2021, founded the 55/Redefined Group, and set about tackling that last ‘ism’ – ageism – from every angle.

Today, that group of companies includes Life/Redefined, our consumer brand, plus Jobs/Redefined, the UK's first dedicated over-50s jobs board and Work/Redefined, which enables businesses to attract, grow and engage over-50s talent to work for them and over-50s consumers to engage with them.

All In A Day’s Work

Of course, the Bold Future Award isn’t Simpson’s first rodeo. She’s already been recognised in the ‘UK’s Top 35 Businesswomen’ by Management Today and The Sunday Times, and is one of the ‘UK’s 50 Most Inspirational Female Entrepreneurs'.

At the champagne breakfast where the shortlist was announced, many of the UK's key media gathered to hear a short Q&A by each nominee as they told their stories of what made them a Bold Woman nominee.

Now in its 52nd year, the Bold Awards are the longest-running international awards of its kind. Showcasing outstanding UK female entrepreneurship and innovation through key events across the world, Bold by Veuve Clicquot supports women entrepreneurs and gives them a voice, encouraging future generations to be even more audacious. The Bold Woman Awards consist of two categories: the Bold Woman Award and the Bold Future Award. The first recognises a track record of organisational and personal success; the second spotlights up-and-coming entrepreneurs, which Lynsdey has been shortlisted for.

The winners will walk in the footsteps of some of the most impressive female entrepreneurs including: Professor Dame Sarah Gilbert the inventor of the Oxford AstraZeneca COVID vaccine, Jo Whitfield, CEO of Co-Op Food, Poppy Gustafsson OBE, co-CEO of Darktrace and Tessa Clarke, co-founder and CEO of Olio.

Invitation to the Veuve Clicquot Bold Woman Award announcement

“I hope to inspire today’s 50+ generation and everyone that follows them to be bold, and ignore the societal expectations and limitations placed on work and life based on age. We should start referring to age in levels, because “I’m at Level 45” sounds far more powerful! I can’t wait to master the levels ahead of me!" Lyndsey Simpson.

Advocating For Women (And Men Too!)

And it wasn’t just Lyndsey getting the voice of women heard that day. While she was being feted in the media spotlight, our Chief Strategy Officer, Natalie Hall, was down the road in the hallowed halls of Parliament, giving evidence to the Women and Equalities Commission about the plight of over-50s and the changes that need to be made to get more over-50s back into employment.

The social impact of the 55/Redefined Group is something that has always been on Lyndsey’s radar, and our past groundbreaking reports: “The Unretirement Uprising” and “Shut Out, Forced Out and Overlooked” have both shone a light into the many issues affecting men and women over 50 and the changes that need to happen for older workers to be free from the often-implicit ageism that happens in employment.

But it’s not all about the cause. Work/Redefined is helping businesses understand it’s not just the over-50s who need them. They need the over-50s in their workforce, helping to fill skills gaps and mitigate for a shrinking population. The company’s products and services continue to grow and businesses are starting to realise the business imperative of becoming age-inclusive employers. 55/Redefined also continues to grow its global presence. In 2023, the company was brought into the MasterCard Start Path startup engagement programme, the second US-based initiative that has seen the company grow its presence internationally. (55/Redefined has also participated in the Accenture Partnership Fund.)

World domination? When you're a Bold Woman, It’s all in a day’s work.

Q&A With Lyndsey Simpson:

A quick life motto you swear by?

What goes around, comes around.

The last book that left a lasting impact on you?

Gentelligence, published in 2021. It’s US in focus, but globally applicable and considers the impacts of a multigenerational workforce.

What’s your best hack for clear thinking in the boardroom?

My Remarkable notepad for preparing and reviewing my previous board notes and movement to a power tune with the volume up loud! My current favourites are ‘Trustfall’ by Pink and ‘Girl of Fire’ by Alicia Keys.

What’s your golden rule for public speaking?

Embrace the silent pause & repeat the key message twice to land it.

What’s the most rewarding part of your job?

Having people write to me from around the world, sharing that we have changed their minds or lives for the better.

And the most memorable leadership lesson you’ve learned so far?

Always hire for what you need tomorrow and not what you need today.

One productivity hack that keeps you on top of your game?

Time is my most valuable commodity. I don’t waste it on activities that I can pay someone better to do it, and I know that I'm not saving money by using more time.

The advice that you’d give to your younger self starting in the business world?

Create your own CRM system with every contact you meet and maintain it like your future depends on it.

What unique skills do you think women bring to the table in a business environment?

I don’t think it’s as linear as all women or all men. But in my experience with the brilliant businesswomen I’ve worked with, they have a level of emotional intuition that shines through and a ‘get sh*t done’ type of productivity, as they are as busy outside of work as in it.

The winner of the Veuve Clicquot Bold Future Award will be announced on the 13th of June, at the Royal Opera House, London.