Conversation with… Joe Pennington
In this latest Conversations interview, we chat with retail leader Joe Pennington about his journey from market stalls in Liverpool to heading up major retail teams.
He also shares how his early love for selling shaped his career, what drives him as a leader, and his thoughts on the challenges and opportunities facing retail today.
Can you tell us a bit about your career journey and what led you into retail?
I have had an amazing career to date and have had the pleasure for working at brands such as Charles Tyrwhitt, ProCook, World Duty Free and Ralph Lauren. My passion for selling and being front of house all started when I was a kid in Liverpool, around ten years old. I’d take ornaments, pots and pans out of the house, pop them in a bag, and sell them on the street corner. My mum wasn’t too pleased when she found out, but I absolutely loved it!
From there, I went on to work on a fashion stall in the market when I was 14, selling jeans to my mates and people from the neighbourhood. I just loved being out front – that buzz of connecting with people, talking, persuading, selling.
When I left school, I joined the Youth Training Scheme – that was my official start in retail. I landed my first full-time job with Burton’s in Church Street, Liverpool, and then moved to London in the early 1990s for my first manager role. I’ve never looked back since.
Subscribe to TRBWhat inspires you most about working in retail, and what keeps you motivated as a leader?
Retail’s a wonderful career choice. The people you work alongside and the energy you create makes for great place to work. The energy you get when everything’s working, the right team, the right product, and customers who are genuinely engaged, is electric.
There’s no better feeling than seeing a customer walk out with a smile and a bag full of goods they’re genuinely pleased with. After all, they’ve taken the trouble to come into a store, the least we can do is make their day a little brighter. That’s the magic that brings customers back in.
As a leader, I get the same buzz when spending time with the team, helping them grow, supporting them to unlock their potential and creating a strategic plan that starts small but has the momentum to move at pace and grow with those involved
How would you describe your leadership style? What makes an effective retail leader today?
My leadership style is rooted in openness and honesty. I believe in giving genuine feedback and coaching the team to fulfil opportunity. I lead from the front and share the highs and the lows and if we fail, we get back up and go again.
Integrity is everything to me, and I expect it from others too. We all get up early, get ready, and show up for work because we want to make a difference. The key is to do it smartly, creatively, and with heart. If you don’t enjoy what you do, there’s just no point coming in.
Looking back, what do you regard as your biggest achievements and lessons learned?
I’ve always loved my “firsts”, including my first store manager role, my first area manager role, my first regional and head of retail positions. Each one taught me something new. None of it happened overnight – it’s been 30 years of graft, fun, and constant learning.
One of the standout chapters was working at Heathrow with World Duty Free for six years. Picture it – 5am, offering travellers a sample of Baileys as they head to their gate, and selling two bottles for £20 before sunrise! You’d be amazed how many people fancy a Baileys at that hour.
Then there was my time at Charles Tyrwhitt, which was a real milestone. I joined just before COVID, and one of my first tasks as a Retail Director was closing 40 stores – that was heart breaking. But the resilience of the team was incredible. We rebuilt, reopened, and came back stronger than ever. The camaraderie that created was huge and the renewed passion to move forward was seen throughout the business.
What do you think are the biggest opportunities and challenges in retail right now?
The biggest challenge, without question, is footfall. If you can’t get people into your stores, you don’t have a business. In the simplest of terms, this is why marketing, storytelling, and the customer experience are so critical. It’s what brings customers back.
Once they’re through the door, it’s about conversion. You need great people who can engage, listen, and create moments that make customers want to buy and increase their basket size.
Whether it’s a small high street store or a 500 person operation at Heathrow, it’s about creating an environment where people thrive. Because when your team loves where they work, your customers feel it too.
Tell us a bit about your home life and family
I’ve got quite the gang! Carlie and I have four wonderful kids but I would say that wouldn’t I. Harry’s 26, Freddie’s 22, Poppy’s 15, and little Primrose is three. All six of us at home and we have two eight-year-old bulldogs to chase after, so it’s a lively house.
Primrose has everyone wrapped around her little finger, of course. The boys’ girlfriends adore her, and Poppy’s brilliant with her too. It’s chaos sometimes but it’s full of love.
What advice would you give to aspiring leaders?
Love what you do, lead with integrity, and never stop learning. Work with the teams, listen to them and hear what your customer wants. Retail rewards energy and authenticity – if you bring both, you’ll go far.
