An e-commerce business with excellent retention and a costly acquisition problem brought me in for a two-day innovation hackathon. The approach combined the Strategy Choice Cascade with Design Thinking to move the team beyond surface-level marketing tactics and toward genuine strategic differentiation, with the winning concepts feeding into the medium-term product roadmap.
The retention numbers in this business were strong. A clear majority of first-time customers returned for a second purchase, and once customers reached the fifth order they tended to stay. The acquisition numbers told a different story. The cost to acquire a customer was high, the business did not break even on a customer until the fourth or fifth purchase, and there was a heavy dependence on paid search competing against a trusted high-street competitor with brand recognition the business could not match.
A previous offsite had generated marketing tactics. The team had landed on the view that tactics were not enough, and that what was needed was strategic differentiation. Blue ocean thinking, in their own framing. Genuine reasons for a customer to choose this business over the alternative, and a way to pull them in that did not rely on paying more for the same search keywords.
The brief was a two-day hackathon for two competing teams of five, one from each of the business's two technology platforms. The output to be reviewed by the most senior leader in the room at the close of day two.
I combined Roger Martin's Strategy Choice Cascade with Design Thinking. The cascade gave the teams a strategic spine, five questions that forced honest answers about where to play and how to win. Design Thinking gave them a way to translate those answers into prototypes a customer could actually see and use.
Day one was about strategic thinking, with no idea generation in the morning. I opened with a Beginner's Mind session: fresh outsider perspective on the customer journey, deliberately questioning the things the team had stopped noticing. What customers tolerated about the current experience but should not have to. The morning then worked through target audience, ambition level, and how-to-win framing. Only after lunch did the teams move into How Might We statements, rapid-fire ideation, idea collisions, and the stress test I use to separate strong concepts from popular ones: what would have to be true for this idea to win?
Day one closed with each team holding a single key concept brief, ready for prototyping.
Day two moved to prototype development. Two rounds of building, with refinement between them, and an informal walk-through by senior leaders late morning. The focus was Wizard of Oz prototypes: clickable, scrollable, full customer journeys that simulated the experience without needing the technology underneath. A technical developer pool was available as consultants for feasibility questions. Final presentations to the most senior leader in the room closed the second day, with a small prize for the winning team.
The hackathon delivered two prototyped concepts, each grounded in a Strategy Choice Cascade answer, each tested against the what would have to be true question. The winning ideas were committed into the medium-term product roadmap with a defined path forward: customer journey validation through user testing, wireframing and specification, resource assessment against the current backlog, and project initiation dependent on idea type and dependencies.
Beyond the concepts themselves, the hackathon shifted how the teams thought about acquisition. The frame moved from marketing tactic to strategic choice. From cost-per-click to reasons-to-switch. From a red ocean of search bidding to a blue ocean of customer experience design.
The reason the Strategy Choice Cascade pairs so well with Design Thinking in an acquisition context is that the two frameworks discipline each other. The cascade stops Design Thinking drifting into customer empathy without strategic implications. Design Thinking stops the cascade ending in a slide deck nobody can act on. Together, by the end of day one, the teams had a single concept each that was both strategically grounded and prototypable.
For digitally native businesses with strong retention and weak acquisition, the move is rarely a new acquisition channel. It is a strategic re-frame of why someone would choose you in the first place, surfaced through customer experience design and tested against the discipline of what would have to be true. That re-frame is the work this format is built for.
Most work like this starts with a 30-minute call to understand the team, the context, and what good would look like. From there we agree the shape of the work together.
