In this episode of Selling the Cloud, we sit down with Josh Hoffman, a seasoned go-to-market leader who has guided sales transformations at Dell, Avaya, Poly, Datto, and now ControlCase. Known for his “sell-with” philosophy, Josh shares what it really means to drive symbiotic outcomes, where sellers, partners, and customers win together.

He unpacks lessons from decades of leading in high-stakes environments, including mergers, market pivots, and rapid scale, and makes the case for consistency, humility, and emotional intelligence in modern sales leadership. From shifting away from zero-sum thinking to building customer-aligned mutual action plans, this episode is a masterclass in outcome-based selling and team-driven success.

What You’ll Learn

• Sell-With vs. Sell-To: Why Josh believes the most successful sellers don’t “close deals”, they solve problems alongside the customer.
• How to Build Mutual Action Plans: Practical ways to bring partners and clients to the same side of the table from day one.
• The Role of AI in Sales Coaching: How Josh’s teams are using AI for prompt writing, context synthesis, and deal prep, without losing the human element.
• Coaching Through Change: Why consistency, not charisma, helps teams thrive through high-pressure acquisitions and pivots.
• From Manufacturing to CRO: Josh’s story of going from putting screws in motherboards at Dell to building global GTM teams, and what shaped him along the way.

Key Topics

• Transforming sales cultures from transactional to consultative
• Teaching sellers to ask better questions, and when to talk less
• Why top sales leaders reduce the distance between themselves and the AE
• Coaching through ambiguity and building career-defining moments
• Why consistent behavior builds trust in times of change
• Using AI to augment, not replace, frontline coaching and prep

Guest Spotlight: Josh Hoffman

Josh Hoffman is the Chief Revenue Officer at ControlCase and a proven sales leader with over two decades of experience building high-performance teams. With a track record of leading in moments of transformation, Josh is passionate about coaching sellers to exceed what they thought was possible, through shared success, customer obsession, and scalable systems of growth.

Resources & Mentions

• Book: The Qualified Sales Leader by John McMahon
• Book: FYI: For Your Improvement by Korn Ferry
• Company: ControlCase (compliance & audit automation)
• AI Tool Mention: Grammarly, prompt engineering
• Leadership Inspiration: Todd Abbott, Mike Jenner, Mark Anderson

🎧 Listen now on Apple Podcasts, Spotify, or wherever you get your podcasts.

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