Meet the new Co-Owner and Commercial Director Simon Leeming

Software solutions can be interpreted as a ‘magic button’ for some businesses. But for Simon, with years of experience in the software industry, the best solutions aren’t so simple. 

As the Co-Owner and Commercial Director at Bespoke Digital Agency, Simon champions the principle of ‘clarity before configuration’. It’s a lesson learned from cutting corners at the start of a project, which ultimately leads to rework and frustration as the initial discovery, process mapping or structural planning was missed. 

“Technology is just the framework. The real value comes from aligning it to the business's actual process.”

In an era where businesses are quick to automate with AI, Simon advocates for a ‘strategy-first’ mindset. He believes the future doesn’t belong to companies with the most tools, but to those who properly integrate AI and the right software across marketing, web and sales. Success lies in creating a digital ecosystem where every digital touchpoint serves a clear, commercial purpose. 

The Enterprise ‘Lightbulb Moment’

The focus on software and process alignment was developed from nearly a decade in enterprise software sales. While Simon enjoyed a successful career, he was exposed to recurring frustrations. Even in large, well-resourced organisations, there were still gaps in how sales and marketing teams communicated. 

“I realised I could provide genuine value by fixing that disconnect”, Simon says. This led him away from sales and into the agency world. Today, that background acts as a ‘commercial lens’ for Bespoke Digital Agency. Simon ensures every decision is rooted in commercial clarity and aligned with the client’s revenue goals. 

Building a Diamond Legacy

The strategic acquisition of Bespoke Digital Agency was the natural next step, allowing the expanded team to lead with their expertise as a Diamond HubSpot Partner. Building on this, Simon and Co-owner Dave Watson have ensured the agency’s technical depth remains focal as they scale. 

This move brought together 25 specialists, collaborating across HubSpot and CRMs, B2B marketing and custom web development. Under Simon's commercial guidance, Bespoke Digital Agency doesn’t just offer services; it provides an engine, designed to handle the sophisticated needs of mid-market and enterprise clients. 

A Supportive Leadership Style 

On a day-to-day basis, Simon supports strategic consulting, new business development and manages the HubSpot partnership. He leads with a style that favours openness and collaboration over corporate formality. To Simon, being supportive and structured isn’t just about internal culture; it’s demonstrating the same capability and trust to clients. Outside of work, Simon is a proud dad to a two-year-old son and a lifelong rugby fan, following Ireland through the Six Nations. 

“Growing this agency and consistently improving what we do means coming to work genuinely never feels like a job.” 

Moving from Uncertainty to Clarity 

Simon’s vision for Bespoke Digital Agency is to be the most credible, trusted and experienced digital partner for mid-sized and enterprise B2B organisations. He wants to help businesses move from digital uncertainty to operational confidence, giving them the infrastructure they need to succeed.

Want to learn more about HubSpot? Chat with Simon today.