Inspiring Women: Vicky Critchley – Rewriting the Rules with Empathy, Courage and a Little Healthy Competition

Some conversations feel effortless from the start. My chat with Vicky Critchley, CEO of TrulySMB and Entrepreneur of the Year 2024, was exactly that.

Her story is one of resilience and reinvention; a woman who learned early on that sometimes the best way to lead is to quietly rewrite the rules. She has built a career, and a company, powered by empathy, authenticity and a streak of healthy competitiveness.

Vicky tells me she owes her start in technology to her dad, who once read in The Sun that computers were going to be “the next big thing.”

“He told me to sign up for a computer course,” she smiles. “I had no clue what that meant – I hadn’t even done computers at A level.”

So she did what seems true to Vicky’s style: she jumped straight in. Nottingham Trent, Computer Science, the only woman on the course.

I ask how that felt.

“At the time, I didn’t really think about it,” she says. “I just got on with it. Looking back now, I probably should have noticed, but I didn’t. I was just doing my thing.”

That sense of determination and quiet self-assurance seems to follow her everywhere.

Her early career took her from the UK to Australia, and later to Silicon Valley – an experience she still describes as “very cool,” but one that came with its lessons.

“It was before the dotcom bust,” she says. “We spent money on silly things. It taught me a lot about what not to do when I eventually ran my own business. The tech industry can feel like its own planet sometimes, but it’s still a business with people at its heart.”

Even then, female role models were rare. “I didn’t really think about it at the time,” she admits. “I was just competitive – probably with myself more than anyone else.”

Years later, when she began leading her own business, that reflection shaped the kind of leader she wanted to be.

“There were things that happened when I was younger that were totally out of order. If I’d been a man, they wouldn’t have happened. So when I became a leader, I decided that stops here.”

Motherhood brought another defining moment. She recalls being told by a former boss that her career was “over” and that she needed a “lifestyle job.”

“I think I actually believed him for a while,” she says reflectively. “I spent a long time thinking I wasn’t doing work very well, and I wasn’t being a mum very well either.”

It’s a sentiment I understand – and I’m sure many mothers do too.

“But I love what I do,” she continues. “I love working. It took time to realise he was completely wrong.”

That experience stayed with her. It made her want to create something different for the women – and men – who now work for her.

“Show a little heart in leadership, and you’ll always get more back in return.”

At TrulySMB, empathy isn’t a policy; it’s a daily practice.  “It’s about understanding that everyone’s got their own thing going on,” she explains. “People have lives outside of work. When you recognise that, they give you their best.”

Vicky believes the Covid pandemic played a big part in reshaping how people show up at work.

“Before, people had a work persona and a home persona,” she says. “Covid merged those together. Suddenly, we were all in each other’s homes. It made us more real.”

And in Vicky’s world, being real matters.

“You shouldn’t have to be two different people. Be yourself at work, and you’ll do your best work.”

Her approach runs deep, from flexibility to fairness. When I ask about pay equity, she looks almost puzzled.

“We don’t have a gender pay gap. I pay people for their skills, not their gender. I don’t even know what a pay gap means – it shouldn’t exist.”

“Empathy and ambition aren’t opposites; they’re what make leadership work.”

When we move to the topic of AI, her voice lifts slightly. The self-confessed “tech nerd” in her makes an appearance.

“It’s the most exciting time I’ve ever seen in technology,” she says. “The pace of change is unbelievable. But I want small businesses to benefit from it, not get left behind.”

TrulySMB helps SMEs navigate technology in practical, affordable ways.

“We’re not about selling big, expensive projects,” she explains. “We want small businesses to punch above their weight – to use AI to save time, grow faster and compete with the big players.”

She’s particularly passionate about freeing people from repetitive work.

“If AI can do your spreadsheets, that gives you an hour back to think, create, lead. That’s what excites me.”

“I’m a nerd, but a nerd who believes tech should make life better for people.”

Outside of work, Vicky channels her competitiveness through fitness. She competes in Hyrox events and uses exercise as her way to switch off.

“I’m competitive, probably to a petty level,” she smiles. “But it’s me versus me. Fitness gives me space to switch off from work. You can’t think about emails when you’re sprinting.”

That same focus runs through her leadership – pushing limits, staying grounded, always learning.

Before we finish, I ask the question we put to every woman in this series: who inspires you?

She pauses, laughs, then says, “Can I be really pathetic?”

Of course.

“It’s my husband, Brett,” she says. “He’s one of the most empathetic people I know. He’s always been successful... but more than that, he leads with heart.”

It’s a simple answer, but somehow the perfect one.

Speaking with Vicky is a reminder that empathy – wherever it lives – is what truly changes the game. It’s what helps people build careers that feel fulfilling, not consuming.

They say it takes a village to raise a child. Maybe that village looks different now. Maybe it’s the people we work alongside each day – the colleagues, the mentors, the leaders who make space for us to be human.

A huge thank you to Vicky for her time and openness in sharing her story.

You can watch the full interview on YouTube https://youtu.be/4tKI0P71EM8

and discover more about TrulySMB. https://trulysmb.co.uk/