HARRY O'BRIEN

The Challenge

Harry transitioned from agency sales to SaaS, facing longer and more complex deal cycles without clear RFPs or set buyer journeys.

“Previously I was in agency sales — usually RFP-based with one main stakeholder. In SaaS, I quickly realised single-threaded deals are too vulnerable.”

Used to linear sales processes, he needed to understand how to operate in multi-threaded, evolving SaaS deal environments where ambiguity is the norm.

The Solution

A flexible, consultable framework for running every deal like a pro.

“Even as far as two weeks ago, I was working on a deal and went back to the proposals chapter as a refresher. It’s like a playbook I keep on-hand.”

Harry didn’t just watch the course once — he used it as a live tool. By applying each chapter to real deals, he was able to adapt quickly, strengthen discovery, and master multi-threading with confidence.

“The multi-threading chapter helped me approach stakeholders in a way that doesn’t feel like a hard sell — just the right next step.”

The Impact

Harry closed a multinational deal within just 8 weeks — nearly half the usual cycle — and upsold a second territory into the deal.

“We got to proposals within six weeks. The structure helped us build rapport faster and move with more control.”

The deal size increased significantly, and he now uses the discovery tactics daily to qualify faster, reduce wasted time, and win trust earlier in the process.

“That one question — ‘Can you tell me when this became a problem?’ — has changed my discovery conversations completely.”