In this episode Jack talks with Sherridan Wills (Head of Enablement at Reputation) about the real purpose and power of sales kickoffs. They argue kickoffs are far more than parties — when designed strategically they’re the single most powerful tool for organizational alignment: communicating go-to-market strategy, rolling out new products, and unifying messaging across regions. Sherridan walks through how enablement’s role has matured from event-production to strategic orchestration — building a cross-functional team, defining clear learning objectives tied to business outcomes, and insisting every session be actionable (not just informative).

They dig into practical planning: start with the “why”, invest in high-impact learning (workshops, simulations) over spectacle, and hold presenters to practice and facilitation standards so sessions aren’t “death by PowerPoint.” Sherridan also highlights underrated details — cultural sensitivity, dietary/logistics, pre-work microlearning — that massively affect participant readiness and long-term impact.