What if the root cause of your outbound problem isn’t the people but the system? In this episode, I’m joined by Gerry Hill, VP at ConnectAndSell and creator of Pipeline OS, to cut through the noise around sales development and give you a blueprint for scalable, effective pipeline generation.
Gerry’s seen firsthand how most sales orgs are wasting time, money, and talent by focusing on the wrong things tech stacks over structure, "charisma" over rigour, meetings over behaviour. We talk about how to fix that. From restructuring SDR workflows to leveraging gamification and agile frameworks, Gerry walks us through how to turn your outbound chaos into a repeatable engine for revenue.
If you’re a sales leader fed up with underperformance and overcomplication, this one's for you.
How to build pipeline development systems that actually work
Stop romanticising "sales artistry" and focus on the science: disciplined execution, repeatable process, and tight feedback loops.
Use MECE (Mutually Exclusive, Collectively Exhaustive) thinking to segment work, avoid cross-threading, and drive clarity.
Pre-build the outbound week: define lists, scripts, execution windows, and follow-ups—then let reps iterate and learn.
Shift comp plans to reward behaviours, not just outcomes—introduce a points-based gamified system.
Borrow from agile: treat outbound campaigns like sprints, with reps acting as scrum masters.
Create systems where managers manage again—your process should do the heavy lifting on accountability and clarity.
Timeline summary
[01:45] – The biggest problem in sales leadership? Homogeneity and lack of shared mission.
[03:32] – Why curiosity is the #1 trait Gerry hires for—and how it correlates with top performance.
[05:04] – How to measure curiosity in interviews: chaos, not canned questions.
[06:47] – Why complaints are a gift: they signal engagement and highlight blockers.
[10:13] – Reps don’t need coaches—they need missions, systems and heroes’ journeys.
[13:41] – Pipeline is strategy, not grunt work: why most teams are structuring it wrong.
[14:32] – The power of the MECE framework in outbound design.
[17:16] – Making boring-but-important work fun: points-based comp and behaviour-led incentives.
[20:07] – Pipeline development = agile sprint. Here’s how to run it like software engineering.
[22:33] – Don’t have a system? Then your tech stack is a liability, not a lever.
[26:59] – Real servant leadership is not about being nice. It’s about hard-edged, mission-driven service.
Links & resources
- Gerry Hill on LinkedIn: https://www.linkedin.com/in/beaccurate/
- ConnectAndSell: https://connectandsell.com/
- Pipeline OS: https://connectandsell.com/pipeline-hero/
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