At Flexa, we believe that every career journey is unique, and we’re excited to launch our Career Spotlight series to celebrate the diverse paths that have shaped our team. In this series, we’re inviting our employees to share their personal stories, insights, and experiences. From how they got started to the challenges they’ve overcome and the lessons they’ve learned along the way. Whether it’s a journey from commercial operations to co-founder or from developer to team lead, we hope these stories inspire others to see the possibilities within their own career journeys. Stay tuned as we explore what it’s really like to work at Flexa through the eyes of the people who make it all happen.

Starting a business like Flexa is no small feat, and Maurice O’Brien has been instrumental in turning the vision into reality from day one. From laying the groundwork to steering the business through the challenges of scaling, his journey offers invaluable insights for anyone aspiring to become a founder.

Hi Maurice. What inspired you to start Flexa, and how did the idea take shape?

Flexa actually began as a pub conversation! Molly and I were talking about the lack of transparency in the workplace, and how great employers could overcome this by being crystal clear about what their working environment looked like. 

I had worked as an MD at a FTSE100 firm which had embraced hybrid working (long before Covid!) and I’d seen first-hand the benefits this had brought in terms of talent attraction and retention. Molly saw things from the opposite side: due to her autoimmune condition, she desperately needed to understand what the working environment would be like at a prospective employer.

We chewed on the idea for a while, until Molly bought me a whiteboard and told me “you’ll never get started if you don’t write it down!”, and thus Flexa was born.

What skills from your previous commercial and finance roles have been most useful in your journey to becoming a founder at Flexa?

There are definitely a ton of transferable skills that I was able to bring from the corporate world into a startup. From the financial side, it’s very valuable having a co-founder in the team who is innately close to the numbers and how the business is growing (not to mention cost control)!

From the more commercial side, I previously worked as a “General Manager”, overseeing many parts of a business and ensuring a broad range of teams were tightly aligned. Being a true generalist is enormously helpful when running a startup, as it feels natural to context switch between marketing, product, finance, ops, etc.

How do you balance being a visionary for the company with the day-to-day realities of running a business?

I think this is one of the most challenging aspects of running a business. In a corporate role, once you get to the ‘visionary’ stage, the day-to-day bits are inevitably somewhat behind you. When it comes to a startup, you need to set strategy whilst also being “in the weeds” when necessary (e.g. I still look after our accounts and our legal contracts). 

One thing that has definitely helped here is having a co-founding team with a broad skill set. Molly loves the visionary / brand building stuff - so she leads on that!

What’s been the most rewarding part of watching Flexa grow?

I’m really proud of the team and culture that we’ve built here. 

For a startup that began with 3 founders in 2020, we’ve managed to build an incredibly talented team, underpinned by a genuinely awesome culture…. and we’ve done that largely remotely!

More than anything, this is a reflection of practicing what we preach. We’re super intentional in describing what it’s like to work here (e.g. it’s flexible, but it’s hard work) and that has led to true talent alignment. 

How do you define success for yourself and for Flexa?

The ultimate success for Flexa would be that it becomes a ubiquitous household name, such that jobseekers would query why a company wasn’t on Flexa.

Success for myself is being a part of that, and eventually getting some time back to chill out with Molly and our dog!

What’s one lesson you’ve learned as a co-founder that you’d share with someone starting out?

Take advice with an enormous pinch of salt, especially from people who have not been in your position. Everyone has an opinion, but not everyone is right, and you know your business better than anyone.

Caveat: if everyone is telling you the same thing, stop and think why - you’re probably wrong (or, less likely, a genius)! 

What’s the hardest part of being a co-founder that people often overlook?

Decision fatigue is the most overlooked factor. Everyone knows that being a co-founder is onerous, stressful, etc, but decision fatigue is the piece that creeps up on you. 

There are an enormous number of minor decisions to be made on any given day, and that eventually becomes exhausting. As a result, I try to minimise decision making in my personal life!

If you could go back and give yourself one piece of advice when starting Flexa, what would it be?

It’s quite hard to narrow it down to one piece of advice.
From a people perspective, it took us a while to work out the types of skills, attributes and attitudes we needed to hire for. I wish I’d known this from the start.

What advice would you give to professionals who are considering transitioning from a commercial or finance career to becoming a founder?

Dip your toe in the water first. Making the leap is challenging, and the opportunity cost can be substantial (i.e. you will usually earn a lot less money as a founder). It’s also risky, especially if you have dependents.

Personally, I worked 3 days a week as a contracting consultant whilst getting Flexa off the ground and raising our first funding round. I only went full time on Flexa once we were comfortable enough to do so. 

Share your career journey with us

Everyone’s career story is unique, and we’d love to hear yours. How did you get to where you are today? What challenges did you overcome, and what lessons have shaped your path? Whether your journey has been a straight road or a winding one, your story could inspire others to embrace their own career adventures.