The Fishbowl: Tess Thompson, City Outdoor

The Media Leader’s interview series asks the media industry’s top salespeople revealing questions, drawn from our fishbowl. The questions are drawn at random and contain some tricky posers set by the commercial chiefs themselves.

This week, it’s Tess Thompson, managing director at City Outdoor.

Tess Thompson started her career as a business development manager for digital OOH at Kinetic, becoming a senior account manager in 2008 and account director in 2012.

She later worked at MediaCo in agency sales and business, before moving to Signature Outdoor in 2015 as head of specialist sales.

Thompson joined City Outdoor as national sales director in 2016 and was promoted to managing director this year.

When you were a child, what did you want to be when you grew up?

When I was young, I basically wanted to be Madonna. Any chance I could get, I was dressing up and singing. I was at a performing arts school for most of my childhood and teens — always in shows and pantomimes, and was most happy being on the stage.

At university, I studied English Literature and American Politics, and ultimately wanted to be a current affairs journalist, breaking news stories across the world.

As you can see, both professions are very closely aligned with what I’ve ended up doing!

Who’s your best friend in the industry?

I’m lucky enough to have a good few people I call great friends in the industry, which I guess comes with having been working in it for so long.

My team have become a work family over the last eight years — working so closely together in the way that we do, we have all become a very tight network of friends. We know far too much about one another, to be honest!

Why are you passionate about media?

For a media channel which is the oldest form of advertising, it always amazes me how it keeps evolving and innovating.

Opportunities like programmatic, 3D, augmented reality — it’s a forever-progressing medium. However, for us at City Outdoor, we are also proof that it’s often the simplicity of a bold site in a great location that can really land a campaign and bring an idea to the real world.

I think of our industry and the bounceback we’ve seen since Covid-19 (who could have predicted there would be a time when literally no-one was out of home!) — how specialists and media owners really worked together through the toughest of times as businesses to create the resurgence we are seeing now.

I still maintain that relationships are everything and it’s one of the key reasons I enjoy it so much, so I guess I’m passionate about media because of moments like these.

Describe your leadership style.

At City Outdoor, it’s very collaborative. There’s a very open ethos and real autonomy across the whole team, where everyone’s opinions are considered before bigger decisions are made. This is not always easy to uphold within a larger-scale business, I realise, but it works effectively within our structure.

What clients are you most excited about right now?

We love working with H&M; as a brand, they have managed to always stay on top of their game creatively, from their collections through to their beautiful marketing assets. They’ve always been one of my favourite brands.

JD Sports stands out in 2023. They’ve done a brilliant job at incorporating pop culture within the brand with their recent collaborations with Central Cee and Kano. I have teenagers at home who are equally as passionate about sport and music, so these ads are bang on for them and I can see first hand how this tie-up of sportswear and music artists can really enforce a brand’s identity and the iconic yellow bag.

What’s been your biggest challenge this past year and what are you doing about it?

We are a small business in a large and competitive industry, so we will always have the challenge of punching above our weight.

So keeping our sites front of mind and relevant for all categories of advertisers is essential. 2023 was overall a good year for us, so it’s very much about increasing that level of growth across all agencies and specialists in 2024.

Peer question: Who are your role models?

I don’t really have role models, but I take inspiration from so many people around me. I grew up in the specialist world in the early 2000s, at a time where there were minimal women in senior positions across our industry, and I wish there had been more representation at that level when I was starting out.

It’s been promising to watch this improve over the years across all media and we are now living in a time where companies are considering its people much more than they ever did, helping to create positive work environments and hopefully happier employees.

Ultimately, my inspiration right now within the industry would have to be Steve [Smith], the owner of City Outdoor. I think there are plenty of people who speak a good game about how to run a business and keep employees’ happiness at the centre of their culture, but Steve genuinely does.

There has been 0% turnover of staff in 15 years. It’s a simple formula that if people are happy, feeling rewarded and appreciated within their roles at work, they are going to put in their maximum effort into their work and the business will see the best results.

Question from Davina Barker, sales director, Digital Cinema Media

Peer question: What three guests (dead or alive) would you invite to a dinner party and why?

Michelle and Barack Obama (I can’t choose between them both, so can they come as one?) for my political fix, then Jameela Jamil (I’m a big fan of her podcast) for entertainment and conversation, as I tend to love everything she has to say.  And I’d have to have Prince — just because he’s Prince and forever my music hero.

Question from Nick Shaw, chief revenue officer, Ocean Outdoor

Peer question: What, if anything, is your business planning on doing differently this year?

Unlike many OOH media owners, as a business we are not in the habit of building lots of sites. We are approached about site opportunities all the time and we say no to most of them, as we like to ensure that each location offers a standout opportunity for brands.

It makes it more exciting when we do launch a new site — and we are aiming to bring another one-of-a-kind screen in the summertime. Watch this space!

Question from Richard Bon, UK managing director and Europe commercial lead, Clear Channel

Peer question: When did you fail the hardest and what did you learn from it?

I’ve had many failures within my personal world, but that’s for another day. Failing is part of life’s journey and I really believe that without failure comes a lack of progress — it’s what gives you the experience you need to push on and try again.

I try to tell my kids this on a regular basis, but they live in a generation where there are massive expectations for perfection and it’s not allowing for these important “failures” along the way.

I don’t believe that in our industry there is generally a bad choice to make, but personally I started out within the specialist world both trading and then planning, and I learned some valuable foundational lessons for eight years. But perhaps, looking back, I could have made more changes, taken more risks and got into the sales side of the business sooner, as it’s much better-suited to my skillset.

Again, I don’t really perceive this as failure, more a lesson I look back upon and wonder what potential opportunities I may have missed in those early years. So I’d always encourage people to be less afraid of taking risks, as they’re often the best lessons in life.

Question from Wayne Davison, chief revenue officer, Little Dot Studio

Read more Fishbowl interviews here and see what media’s top salespeople say about working in the industry and what concerns their clients. To suggest an interviewee, contact [email protected].