Mums in Tech ft. Hollye Kirkcaldy

As part of our ‘Mums in Tech’ series, we caught up with Hollye Kirkcaldy, Founder & CEO of Venture Upstream.

The purpose of our 'MotherBoard’ content series is to highlight incredible working mums within tech & data, as well as individuals and businesses that are supportive and progressive within their approach to creating more inclusive tech & data teams for women.


Firstly, can you please introduce yourself and tell us a bit about your current role? 

I’m Hollye Kirkcaldy, Founder and CEO of Venture Upstream. We advise tech-for-good start-ups and charities across the South West on commercial and communications strategy. Our mission is to put purpose-driven organisations in the best possible position to attract new sources of funding, including corporate partnerships and investment. 

I’m a journalist originally, and then worked for years at big communications agencies on campaigns for brands like Heineken and Adidas. I started consulting for some European start-ups, got hooked on the tech world and went in-house a few years ago as Chief Commercial Officer at an ad tech company going through that challenging start-up-to-scale-up journey. When I decided it was time for a change earlier this year, I realised that I could combine my learnings from that tech funding rollercoaster with my experience as a comms specialist to really help others so Venture Upstream was born.

If you could sum up what it’s like being a working mum in tech in one sentence, what would it be? 

Most days, it’s like being a perennially exhausted circus performer trying desperately to keep plates spinning in the air while simultaneously juggling full washing baskets with your feet - when it goes to plan, it’s incredibly rewarding and when it doesn’t, you just pick up the pieces and go again.  


“Most days, it’s like being a perennially exhausted circus performer trying desperately to keep plates spinning in the air while simultaneously juggling full washing baskets with your feet - when it goes to plan, it’s incredibly rewarding and when it doesn’t, you just pick up the pieces and go again.”


How do you find the balance between your career and motherhood? 

I’m not really sure I’ve managed to find that elusive balance yet, but arguably I’m getting a little closer now that my children are a little older and I have more flexibility as a business owner. I also have a husband who takes on far more than his fair share of the constant juggling, which helps!

Admittedly, part of my problem is self-inflicted - I find it almost impossible to say no to people or things that interest me personally, so I usually end up taking on far too much. I do have my red lines though, and one of those is to never miss my kids’ school events like sports day and class assemblies. The wave and smile you get when they see you is worth every single hour of working late.

What has been your greatest challenge as a working mother in tech? 

Like most working mums, I imagine, I find I’m never really able to throw myself 100% into work like perhaps I used to do before having my kids. Before children, I could be entirely selfish with my career, work long hours if I needed to, travel for work without really thinking about anybody else. Now, my working day fits around the school run and all the other family life commitments, so I work in shorter, more concentrated bursts – it can be incredibly productive but it also makes it difficult to properly get your head into something complex when you have to keep coming back to it several times. But actually, there is a positive side to all this – I now have a broader sense of perspective than I’ve ever had before, and am very well aware that work simply isn’t the be all and end all. That thought alone keeps me sane.


“I say all the time that there is nobody more productive than a working mum. I get things done because I have to - there’s very little room in a busy day for procrastination. ”


What skills have you developed as a mother that have helped your work life? 

I say all the time that there is nobody more productive than a working mum. I get things done because I have to - there’s very little room in a busy day for procrastination. I’m now more organised than ever, largely thanks to an obsession with writing to-do lists to stop the little things falling through the gaps.

When you were returning to work, what one thing helped you / would have helped you the most? 

When I returned to work after having my first child, we were incredibly lucky to have a vast amount of family support – my parents and my husband’s parents would tag team looking after our daughter on non-nursery days so I could work full time. It was still difficult at times, particularly when all your carefully curated plans fall to pieces when your child brings home yet another nursery bug, but I honestly couldn’t have done it without that support.

I started a new job after returning from maternity leave with my second child but this time chose to work part-time. What helped was that the company I worked for completely bought into the idea that it didn’t really matter where or when you did the job, as long as you did it well and achieved what you needed to achieve. Their rejection of ‘presenteeism’ allowed me to flex my time to both do my job and be a mum, and I’m incredibly grateful for that.


“Don’t lose yourself while striving to be all things to all people, children included. ”


What do you feel should be the top priority for employers who want to support working mothers better? 

A positive approach to flexible working, be that working from home or working part-time hours. It really does make an enormous difference when you’re treated like a grown-up and trusted to make the right decisions which work for you, your family and obviously the business itself.

Any final words of advice for other mothers in the Tech Industry? 

Don’t lose yourself while striving to be all things to all people, children included.


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