Editorial

Women in Digital: Karen Holden 

Karen Holden, managing director of Allin1 Advisory, shares her unconventional route into law and technology, and why resilience, human oversight and greater support for women will be critical as AI and other emerging technologies reshape the industry.

Posted 7 September 2026 by Christine Horton


Did you enjoy school?

I genuinely did not just socially, but I loved my academic studies too. Apparently, from the age of eight, I wrote in my schoolbooks that I was going to be a solicitor. Some things really don’t change!

What qualifications do you have?

I have a degree in Law and Psychology, a Master’s in Criminology from Cambridge, the Legal Practice Course, and I’m a regulated solicitor. I now specialise in advising technology businesses across areas including AI, Web3, and emerging regulation.

Has your career path been a smooth transition, a rocky road, or a combination of both?

Definitely a combination. Funding fell through into my Master’s, so, I couldn’t go straight into law afterwards I had to study part time whilst working. I spent five years in a senior crime analyst role instead. It wasn’t the path I’d planned, but it opened my eyes to a completely different world, and I genuinely believe it shaped the entrepreneur and the person I am today.

Interestingly, that analytical background has stayed with me throughout my career. Over 25 years on, I was already working with profiling systems designed to bring greater efficiency and insight into the civil service, and I have carried that analytical approach into the technology sector. My career has evolved alongside technology from autonomous vehicles and drones, into cryptocurrency and blockchain, and now into AI, Web3 and digital security.

Setting up a law firm has certainly had its rocky moments: a recession, Covid, and constantly having to evolve to keep pace with technology. It’s a fast-paced, traditionally male-dominated industry, and doing things differently has been fun, but disruption comes with its own challenges too – from staffing to the usual pressures every growing business faces. Looking back, it’s honestly been a bit of everything.

What is the best career advice you can give to others?

Don’t be afraid to challenge yourself, and if you make a mistake, learn from it, pick yourself up, and use it to grow. We’re often too fearful to put ourselves forward or risk getting something wrong, but it’s usually those moments that teach us the most. That resilience is what makes a great entrepreneur, and it’s exactly what makes a fantastic employee too.

If you had to pick one mentor who has had the biggest influence on you, who would it be?

It might sound like a cliché, but it’s my mother. She worked several jobs to get me through university and never once questioned why she was doing it. I watched her resilience first-hand she was often treated unfairly, but it never dented her determination, and she never complained. She never pushed me to do anything; instead, she encouraged. That difference has stayed with me.

Where do you draw inspiration from?

Mostly from myself if I see something that could be done better, I want to challenge myself to do it. I need to feel excited and energised by what I’m doing, or I get restless. Beyond that, I draw inspiration from my family, especially my son, who represents the new generation; from clients bringing genuinely innovative technology into their businesses; and from the sheer breadth of experiences this career gives me.

I am particularly inspired by businesses that are genuinely pioneering – whether that is in sports technology, medtech, AI-driven products, or other emerging areas like avatars. Being able to work alongside organisations at the forefront of innovation, often from their early stages, and help them navigate the legal and commercial challenges of scaling is incredibly rewarding.

What is the biggest challenge you have faced to date?

Growing a business, like anyone will tell you, comes with real tests trusting staff, managing cash flow, weighing up opportunities. There are always ups and downs, and it’s particularly difficult when you don’t come from an entrepreneurial family; you don’t have that built-in foundation others might. I persisted through it, and I still do. If I’m honest, dealing with a difficult landlord nearly caused real damage to the business but we pushed through and survived, and that’s probably been the hardest challenge of my career so far.

What qualities do you feel make a good leader?

Leading by example, rather than simply delegating and expecting others to do work you wouldn’t do yourself. Being there when someone makes a mistake, to support rather than criticise. Offering advice when guidance is needed, and motivation when confidence is lacking. It’s not a perfect approach, but it’s the one I take and it’s served me well.

From a work viewpoint, what has the last 12 months been like?

We took the decision to rebrand, as we’ve outgrown being a small, niche City practice, and we’ve also moved offices. That meant a complete overhaul of our marketing and resourcing, which has been genuinely challenging.

Over the last year, we have continued to work with businesses operating at the cutting edge of technology, including those developing AI solutions, autonomous technology, blockchain and Web3 products. Our role is often helping ambitious businesses understand the legal framework around innovation, ensuring they are investment-ready, protected and able to scale responsibly.

It’s constant evolution, but that is what makes working in technology so exciting.

That said, alongside the challenge has come real excitement a new outlook, new staff, new clients, and a real sense that London is booming and busy again. It’s an exciting time to be building something new.

What would you say are the biggest tech-based challenges we face today?

Everyone assumes AI is replacing jobs, but in reality it’s creating a different set of problems. People are over-relying on it and using it badly, which in some ways makes our jobs harder but it also makes human oversight more valuable than ever.

Cybersecurity is a major issue for businesses across the board, so we’re heavily involved in governance and education around it – every business now needs an extra layer of protection built in.

A significant challenge across emerging technologies is also navigating regulation. Many businesses are innovating faster than legislation can keep up. We work with clients to navigate regulatory requirements, draft and negotiate contracts, address liability issues, and put appropriate protections in place particularly where regulation exists but is still developing. This is an area where we have developed particular expertise across AI, autonomous vehicles, drones, Web3 and other emerging technologies.

There’s also a shift towards remote working and heavier AI use, which brings real efficiency gains, but I do think training, social skills, empathy, and understanding can suffer as a result. That’s a real drawback we need to stay conscious of.

What can be done to encourage more women into the industry?

I think honesty is key about the opportunities, yes, but also the drawbacks and the realistic route to get there. Some people are intimidated and simply don’t believe the industry is open to them. We need to be more collaborative and supportive, opening doors and helping each other.

Technology is creating opportunities in areas that did not exist a generation ago, including AI, digital security and emerging technologies. We need more women to recognise that they can be part of shaping these industries, not just participating in them.

Events, educational webinars, and honest literature really help not just by showcasing the opportunities and career paths available, but by being open about the mistakes people have made along the way. Mistakes are human; they build resilience. Nobody should be afraid to take that chance.

Give us a fact about you that most people wouldn’t know.

In 2018, I was one of 100 women awarded the Freedom of the City of London in recognition of equality work I’m genuinely passionate about including work on LGBT sector equality and supporting female founders. It means I can take part in some wonderful City traditions and events, which feels like a lovely, unexpected honour for a tech-focused lawyer to hold.

I also did my thesis on serial killers which stood me well in my first career profiling criminals for the Met Police and assisting in crime analysis and intelligence.

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