Leo Cutler on Scaling eCommerce Inside Large Organisations
In this conversation, he explores how early brand and ecommerce operations roles shaped his leadership approach, and shares practical insights on experimentation, stakeholder influence and scaling ecommerce within complex organisations.
Your Career
How did your early roles in brand marketing and ecommerce ops shape the ecommerce leader you are today?
I was fortunate to start out in traditional brand marketing; that perspective, I think, has prevented me from developing 'ecommerce tunnel vision.' I’ve always viewed a brand’s presence as similar to an orchestra, consumers interact with dozens of touchpoints, and ecommerce is just one vital instrument that must play in tune and in time with the rest.
My time in ecommerce operations then gave me an 'under the hood' look at the business. It provided a deep understanding of the functions behind the storefront, the things the consumer doesn't see, but which must work harmoniously to fulfil the brand promise and proposition. I feel that dual background allows me to work with a creative strategic lens and operational discipline.
Was there a defining moment that changed how you think about ecommerce?
Early in my career probably what hooked me in was the start-up mentality within a large organisation. Testing things, failing fast, learning fast. It is such a fast-moving discipline of digital marketing that you’re constantly trying to move with the speed on the innovation that is going on around you, new trends in checkout experiences, BNPL, Live Shopping & Social commerce, AR to name a few.
What part of your early career are you most grateful for — and why?
My time at Acushnet for the FootJoy brand, working with people that were at the top of their game both on the brand marketing side and in ecommerce. At the time I didn’t realise just what an experience I was getting but I am still living by a lot of the principles that company and those colleagues instilled in me at that time.
Scaling Ecommerce Inside Large Organisations
What are the realities of driving ecommerce innovation inside a legacy organisation?
Driving ecommerce innovation within a legacy organization is a balancing act between global scale and local agility. The reality is that you are often navigating centralised website budgets and a "one-size-fits-all" global web architecture that wasn't necessarily built for the needs of a specific market. You ‘ll face brand guidelines designed for a pre-digital era, requiring your own interpretation with the hope of modernising those standards for a high-conversion, competitive ecommerce landscape. Speed to market can be slower due to necessary layers of governance, however I’ve found that this friction makes the role more strategic. Unlike a small startup where "moving fast" is the default, moving the needle in a legacy environment requires true cross-functional influence and stakeholder management. Because the stakes are higher and the scale is massive, the successes feel far more rewarding; when you finally land a breakthrough, the impact feels real.
What role does experimentation play when commercial pressure is high?
When commercial pressure is high, the instinct is often to retreat to what’s 'safe,' but for me that’s when experimentation becomes most critical. It’s a matter of principle: you need to protect the resource and time for testing and learning because that is the best engine you have for innovation.
The key to doing this under pressure is what I call 'small-circuit testing.' By isolating segments whether it’s a specific section of your CRM database, a portion of web traffic, or an ad set in a paid social campaign, you can de-risk the process. You aren't gambling with the whole success of your project, website or budget; you’re using data to build a roadmap. This approach allows you to fail small and fast, while ensuring that when you do scale a 'next step,' it is backed by evidence rather than just intuition. In a legacy environment, data-driven experimentation is the best way to turn high-pressure 'guesses' into high-impact growth."
If building an ecommerce function from scratch, what would you prioritise first — and why?
If I’m building an ecommerce function from scratch, the priority is probably not the platform, it’s the strategy. That starts with what’s the objective for ecommerce in your business? Is it to complement your existing revenue streams, is it for incremental sales, what percentage of your turnover, or you may simply want to meet your consumers where they shop. From there you can carve out the strategic pillars that are going to get you there. These pillars help day to day decision making align with specific commercial outcomes. Get the strategy right and that keeps things feeling purposeful throughout the year.
Quick-Fire Questions
Podcast, playlist or silence when working?
Music or one of the many Spurs podcasts.
Desktop or mobile shopper?
Big purchases, e.g new bikes, home appliances etc are desktop, more impulsive things I’ll use mobile.
Dark mode or light mode?
Dark mode, save the battery.
One skill you’re currently improving?
Learning about AI, it’s obviously a big focus at BSH and as a country ambassador for AI, I’m trying to learn more.
Best piece of career advice you’ve received?
“It’s easy to start lots of projects, the best marketers get things over the line”, my first manager Russ said that, and I think about it all the time.
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