Lessons from 30 years of Milestone with founder, Jay

For International Women’s Day, we sat down with our Managing Director, Jay Roff, to reflect on 30 years of Milestone and her lessons for future female leaders.

You can also read the next interview in this series with Founder Ian Sutton.

What inspired you to start a business more than 30 years ago?

I’d had the idea of one day owning my own business from my college days. In my first few jobs out of college, I didn’t just want to get stuck into the day-to-day work. I also had ideas for how to improve the businesses I worked in, to make them more efficient. But in those days, they didn’t want to listen to a girl.

By my third job, I realised I couldn’t keep working for people who were so dismissive, so around 1991 I bought my own Apple Mac and set up Fish Design.

After a few years working out of my spare room, I met up with an old colleague – Ian – and we started working together more and more. Ian would create all the concepts, and I brought them to life through the design. By 1995, Milestone Creative was born!

What were some of the biggest challenges you faced in the early years?

The biggest one was finding clients – but we had a really good start thanks to an old contact. We grew quite organically, without needing to borrow much money in those early days.

The other challenge was talking to banks. I jumped through a lot of extra hoops just to be able to open up a business bank account. I had to put together business plans, forecasts for growth and so on – and even then, they acted like I wasn’t serious.

But wouldn’t you know it, that initial forecast was pretty much bang on.

Did you have any role models or mentors who guided you?

First of all – my Mum. She had a job in TV; working while she brought up the kids. The idea of a working woman wasn’t alien to me.

Then there was Sister Kevin, the headmistress at my school. Even though I went to a very traditional girls’ school, Sister Kevin was really focused on education for girls – university was a real option for us, and we were encouraged to think about having professions.

In short, if you can see it, you can be it. And that’s true for everyone. It’s difficult to imagine yourself in a role if you’ve never seen anyone like you in that position. It never occurred to me that I couldn’t go into the workplace.

And now, I have the most amazing women working around me. I get warm inside knowing that I work with all these brilliant, creative women.

How do you think Milestone has changed in the last 30 years?

We’ve changed in so many ways, but it’s been very incremental. We have a bigger team, we work with bigger clients, and we have more processes in place to manage it all.

The environment we work in has also changed – from print-first to a digital focus. I’m very proud that we can adapt to what’s out there, asking “can we do that?” and being able to develop our skillset so “yes we can!”.

One thing that’s never changed is our ethos and our essence. I’ve always been adamant that you can run a business while being decent. Treating your staff well, treating your suppliers well, treating everyone in the chain with respect.

And then, how do you think your leadership style has evolved with Milestone?

I’ve had to learn to let go! Over 30 years, I’ve done nearly every job in the agency, I’ve been the designer and the artworker, I’ve been the account manager, I’ve worn the finance, HR, and even the IT hat. So, I know what I’m asking people to do and what problems might come up. As we’ve grown, I’ve learned how to let others take on some of those roles.

What kind of unique perspectives do you think women bring to leadership positions?

The business world is set up from a male perspective, and sometimes it can feel like any other approach is wrong. It’s not wrong. It’s just different.

Milestone is the way that it is because it’s led by a woman. I’m more interested in making sure everyone – employees, suppliers, clients – is treated with respect and care. For example, if we look after our suppliers and pay them on time, they’re more likely to help out when we really need them.

What advice do you have for future female leaders?

Just to have the confidence that, again, just because it’s different, doesn’t mean it’s wrong.

Don’t be afraid to be a woman. You can be kind and considerate – that’s been our role for forever. Those soft skills are equally as important to business.

And bring other women with you. Be the person that opens the doors – there’s space for all of us…for different perspectives.

We’ve been talking a lot about the last 30 years. I’m curious about the next 30. What kind of legacy do you hope to leave behind, and what are you most proud of?

This business is my legacy, and I’m so proud of the amazing team we’ve built. I hope my legacy is that the business carries on this path, with the same values I gave it, and it keeps showing the world what we can do.

And that’s why I was so excited when I found out that the EOT was something we could do. I knew it was the right fit for us immediately. I’ll be leaving the business in the hands of brilliant people who share the same values and worldview.

And lastly, what excites you most about the future of the industry?

I’m just looking forward to seeing what’s next – we don’t know what it is yet! There’s always something new around the corner and who knows what our core business will be in 10-15 years?

When I left college, we didn’t even have computers. A few years down the line, we were in the midst of the Desktop Publishing revolution which was predicted to be the death of the industry. People thought that now they had computers, businesses would be able to make all their leaflets and so on in house. But in the end, you still needed the creatives to make everything look impactful. Computers became the next tool for us to use.

I’m interested to see if that’s where AI’s going. I hope it’s positive, but I fear that it might not be. Then again, I’ve always been an optimist at heart.