Caleb Shepard: From intern to director

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Caleb Shepard might be just 25 years old, but his list of accomplishments reads more like someone two decades his senior.

The born and raised Durbanite is one of two media directors at The Digital Media Collective (TDMC), and he is currently leading the digital agency’s new Cape Town office. Besides also being an award-winning photographer who has had his work published in Africa Geographic, Caleb was recently named as a finalist in TransUnion’s respected Rising Star Awards. We talk to Caleb about his path to success and industry insights.

Congratulations on being named a finalist in the Transunion Rising Stars Awards which recognise, celebrate, and connect young individuals who possess exceptional talent in their respective fields. Tell us a bit more about this.

I’m really honoured to be nominated for the award. They have been running for 12 years now and there were more than 750 nominees, so I am very excited to be named as a finalist in the Media and Advertising Category. The Rising Star Programme is a wonderful opportunity to be part of a community of like-minded young professionals and entrepreneurs who are mentored and developed with the aim of enabling them to become influential opinion leaders and role models for future generations.

Let’s talk about your role at TDMC and your journey with them from intern to director.

I was fortunate to get an internship with TDMC in 2016 during my gap year after I matriculated from Westville Boys’ High School. I spent the first part of my gap year travelling in Africa and the UK, along with a stint in the Eastern Cape ring-barking alien invasive vegetation. I have always been a keen photographer and videographer – I won an international photography award when I was 18 after I entered photographs from a life-changing trip to Namibia with my family. The prize was an incredible trip to Serengeti – I took my father with me and got to experience the wildlife and unique culture there. As fate would have it, it was my photographic skills that secured my internship at TDMC working in their design department photographing and deep-etching product shots.

I have always been both creative and good with numbers, so I decided to enrol for my BCom specialising in Digital Marketing at Vega, while at the same time continuing to intern with TDMC. During those three years of working and studying I had the flexibility to move across all three departments within the business – creative, web development and media – giving me a great overview of how things worked.

When I finished my degree there wasn’t a place for me in the creative arm of the business, so I spoke to TDMC’s Managing Director, Cheryl Ingram, about taking up a role in the Media division as it tied in with my degree. She agreed, and this offered me a completely new experience, managing client expectations and buying media on their behalf. I learnt a lot about myself during this time and spent many long hours trying to keep my head above water. I grew from an account executive into an account manager, managing a growing list of clients. I really enjoyed working with diverse clients in different fields and gaining an understanding of the complexities of their businesses and their unique challenges. I began pivoting into a strategist role, doing slightly less implementation with more focus on helping the team unpack the clients’ key objectives and defining a media strategy.

Two years ago, I was made Joint Director of the Media arm of the business. My Media Co-Director Melissa Humphry and I are responsible for a team of 35 and we take care of all digital strategy, paid media, data analytics and reporting, and currently service more than 120 clients a month.

At the end of June this year, I moved from our Durban Head Office to set up our new office in Cape Town. I had already been travelling back and forth to Cape Town for the last two-and-a-half years every month for a week seeing my main client, who is one of South Africa’s biggest e-commerce spenders, managing their R6 million per month budget. Although I had got used to living out of a suitcase, it made sense for us to set up an office in Cape Town as it is home to many of SA’s big e-commerce brands. We are currently a team of eight and our client list is growing rapidly – we already have 28 clients in our Cape Town portfolio.

For me, my journey from intern to director is testament to the impact of seizing opportunities, embracing constant learning, and adapting to change within the ever-evolving realm of digital marketing. 

What have been some of your biggest successes during your time at TDMC?

Facebook recently published a case study I conducted for them showcasing the successful use of Meta’s Advantage+ shopping campaigns to maximise ad performance for the South African division of one of the world’s leading adventure footwear, equipment and apparel brands. The results showed that this solution, coupled with business-as-usual campaigns, led to incremental conversion lift and improved efficiencies. It was a privilege to have my work showcased on this global platform. I was also very proud to be invited to take part in a key Meta event last year where I was a member of a guest panel sharing my insights, learnings and recommendations around paid media strategies.

For me, another great achievement is seeing the excellent results we are getting for our global accounts, and the growth in this area.

Who mentored you and what are some of the invaluable lessons you have learnt along the way?

I am naturally inquisitive and curious – I’m a learner and strategiser. I was employee number eight at TDMC – we have now grown to a 50+ strong team – so I spent a lot of time self-learning and self-teaching to gain an understanding of the business as we developed.

Cheryl is a firm believer in exposing people to all aspects of the business at a young age. She would include me in big client meetings giving me valuable insights into how to conduct business at a high level and how to problem solve. I learnt so much about the importance of building relationships with clients and people and I will forever be grateful for that.

How does being a digital native play into your success?

As a digital native I am not scared to test and learn. And this plays directly into my role in digital marketing – in this industry you can’t be afraid of change, and you must be able to adapt quickly. There isn’t a single day when there isn’t a change on one of the platforms we are working on, and we quickly need to figure out a way to work with that. I also have an inherent faith in data – data never lies!