Being Willing to Take the First Step with Simon Ross

Simon Ross is a marketing specialist with 20 years of experience across agency, tech, and client-side roles. Originally from the UK, he relocated from London to Toronto in 2019, and now calls Canada home, especially after recently becoming a Canadian citizen.

Simon is recognised for his ability to connect the dots between media strategy, insights, activation, and measurement, always keeping the consumer at the centre. His audience-first approach has shaped campaigns across diverse categories and earned him regular features in the trade press, where he shares perspectives ranging from connected TV, first-party data, cookieless future, and emerging platforms (amongst many others.) He has also appeared on TV, offering insights into Canadian viewpoints on TikTok.

Throughout his career, Simon has lived by a principle learned early on: be proactive rather than waiting for direction. This mindset has allowed him to continually reinvent himself, through to his current role as vice president of strategy and insights at Horizon Media Canada.

As a leader, he encourages his teams to do the same, creating space for them to take initiative, build confidence, and grow beyond their defined roles. His belief is simple: be proactive because most people aren’t.

The personal values that define Simon are courage, compassion, and connection.

I’ve been given a lot of advice throughout my career, and the one comment that has stayed with me and shaped the way I approach both work and leadership - be proactive rather than waiting for direction.

A senior colleague once said to me in passing, “In the land of the blind, the one-eyed man is king.” I don’t remember exactly who it was, but the words landed. As I have grown in my career, I began to understand its weight. The message was simple: you don’t need to have all the answers, you just need to be the one willing to take the first step.

I learned this early on, while working at a network agency in London. My role was clearly defined but carried broader responsibilities. At the time, I thought my job was to stay in my lane, follow instructions, and deliver on what was asked of me. But that piece of advice shifted my perspective. I realised that anticipating needs, stepping up with ideas, and taking initiative could open doors that being reactive never would.

This advice has also guided me in continually redefining the roles I’ve taken on throughout my career. I started twenty years ago as an email marketing assistant, moved into digital media, trading, international account management, client-side display media lead, business director, ecommerce and innovation, and now a Vice President Strategy and Insights. At each step, I leaned on proactivity to reinvent myself and stay relevant, which is essential in an industry that is constantly reinventing itself as well.

Today, with the rapid rise of AI in media, that same mindset has pushed me to adapt once again. I have immersed myself in AI tools, testing them in my day-to-day work and exploring how they can enhance our approach. I also took it upon myself to bring these tools into our Toronto office, positioning us to stay ahead. I didn’t wait for someone to ask me to lead on AI; I saw the opportunity and stepped into it, knowing it will be fundamental to our roles in the months and years ahead.

This approach not only shaped how I worked but also gave me the confidence to make bigger life and career decisions, like relocating from London to Toronto. That move was filled with uncertainty, but leaning on the principle of being proactive helped me see it as an opportunity rather than a risk.

In agency life, I have often noticed a gap in proactivity. Those who go the extra mile, even in small ways like sharing an article about a client’s industry or flagging an opportunity before anyone else does, stands out because so few people take the time. It is not about grand gestures; it is about showing care, paying attention, and proving you are invested in the bigger picture.

As I have moved into leadership, I have carried this lesson with me. For me, being proactive is not just about standing out, it is about creating clarity and confidence for others. I often tell my team, “We can swim in whichever swim lanes we want.” It is my way of encouraging them to step outside rigid roles and trust their instincts. Watching them grow into that confidence has been one of the most rewarding parts of my career.

In summary, be proactive because most people aren’t. It does not always require bold moves; often it is the small, consistent actions that set you apart. Whether it is anticipating needs, sharing an idea before being asked, or taking the first step into an emerging area like AI, proactivity signals that you care, that you are engaged, and that you are willing to lead. In my experience, that mindset has opened more doors than any formal title ever could.