From Demandware to Breckenridge: Harvey Bierman on TCO, Shopify & The Agency Squeeze”

Inside the SaaS trenches, culture, and why agencies must climb the value chain to survive.

In this Struggle Bus ride, Vinny O’Brien welcomes e-commerce veteran Harvey Bierman — former CEO of Red Van, CDO of Christy Sports, and one of Demandware’s early evangelists — who’s swapped boardrooms for the mountains of Breckenridge. Together they rewind to 2010’s SaaS gamble and fast-forward to today’s Shopify-driven utility model. Harvey’s take on Total Cost of Ownership, agency risk, and fragile “brands” built overnight is as candid as it gets.

Expect a brutally honest, culture-first look at how commerce is changing — and what agencies and brands need to do now if they want to stay on the bus.

• 🚦 Demandware Origins: How four progressive college towns shaped global e-commerce (Burton, Columbia, Deckers/UGG, Crocs).

• 💡 Shopify as Utility: Why the lights-on model is brilliant for merchants but disruptive for agencies.

• 💸 TCO is a Zero-Sum Game: Harvey’s contrarian view on the “Total Cost of Ownership” metric.

• ⚠️ Agency Squeeze: How AI and platform simplification kill low-value work — and where agencies must move (strategy, UX, innovation).

• 🌱 Brands Without Roots: Why low barriers to entry make the industry fragile and why values still matter.

• 🤖 Agentic Commerce: It’s just a blank until smart operators fill it with meaning — and intermediaries are most at risk.

• 🎶 Harvey’s Career Anthem: “Crazy” by Seal — the perfect Struggle Bus mood.

📩 Connect with Harvey on LinkedIn https://www.linkedin.com/in/hlbierman/
💌 Subscribe to The Struggle Bus for future episodes

Thanks to our community partner - Evolve Commerce Club

Sponsored by:Omnisend⁠ - The smartest, simplest and most cost productive way to run email marketing.⁠

Eurobase ⁠ - Ireland's best kept ecomm secret. Perfecting Global shipping for over 30 years. Making complex look simple. Stupid look good.⁠ De Minimis problems? Contact Julie Colclough

Strike Digital⁠ Irelands most Human agency.