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An Interview with Oliver Pickup

by | Feb 16, 2022 | Interviews,

Oliver Pickup

Oliver Pickup

Key Topics:Future of Work, Cybersecurity, Cryptocurrencies, Freelancers
Location:United Kingdom

Oliver is a London-based, multi-award-winning technology and business journalist. He has written for the Financial Times, The Times, DidiDay, The Telegraph, Wall Street Journal, among many other publications.

Oliver has recently featured in Onalytica's Who's Who in The Future of Work Report.

How did you get to become an expert in your key topics?

I started out in sports journalism, in the mid-2000s, and loved reporting human-led stories about boundary-breaking people and teams. When children soon followed marriage my weekends became family-focused, meaning I swapped the sports beat for the tech beat. As a father, I have a vested interest in knowing about the technology trends of today that could shape tomorrow, good or bad. I feel privileged to have been a freelance tech and business writer since 2014. Essentially, I’m still writing about boundary-breaking people and teams.

What sub-topics are you most passionate about?

My general curiosity has taken me deep into the worlds of cryptocurrencies, supply chain, virtual reality, blockchain, cybersecurity, and artificial intelligence (don’t look up “Slaughterbots”). It’s been an honour to chronicle the tech and social trends accelerated by the pandemic, and from my front-row seat I’ve been able to discover how the future of work might look and feel – metaverse happy hours, four- or even three-day working weeks, better support for freelancers, and much more.

Who influences you within these topics?

When it comes to remote working, Darren Murph, GitLab’s head of remote, is always brilliant. I’ve featured Darren, a true future-of-work pioneer, in many articles. Bruce Daisley, who is behind the Eat Sleep Work Repeat podcast, also is high up on my go-to list of thought leaders in this space. MaryLou Costa, a fellow UK freelance journalist, is someone I follow closely, as she is fantastic on women’s policies, gender equality, and diversity. There are many others, too, but these three sit top of the tree for me.

What do you think the future holds in this space?

The future of work is important for everyone in employment today and our children. The latter are likely to look back and wonder why their parents commuted, worked 9-to-5, ticked off 40 hours (or more) of work a week, and didn’t do more to save the planet.

What brands are leading the way in this space?

Darren Murph’s GitLab, which has been fully remote for almost a decade. Also, HubSpot, which was named the best place to work in 2019 according to Glassdoor for good reason. I’m always impressed by Estonian mobility company Bolt, and the way Estonians generally approach technology and collaboration. Collective Benefits, which is aiming to build the freelancers’ safety net of insurance, is also making great strides.

If a brand wanted to work with you, which activities would you be most interested in collaborating on?


I would be open-minded about any and all collaborations. I love hosting and moderating (virtual or physical) roundtables and podcasts, but happy to help with whitepapers, speaking opportunities, and video interviews.

What are your passions outside of work?

Sport remains a passion, and Tuesday nights kicking a football with fellow dads is a weekly highlight. I’m also a DJ: DJ Boat Floaters – see my Mixcloud profile. But most of my time is spent tending to my two small children, from whom I learn the most.

What would be the best way for a brand to contact you?