In this episode, Josh shares how he manages a global portfolio of 170,000 customers by combining data-driven rigor with clear-eyed coaching. He unpacks Asana’s Red Renewals System, a process that flags enterprise churn risk up to a year in advance, giving teams the runway to act before it’s too late.

Alex Raymond is joined by Brent Adamson, the co-author of The Challenger Sale, The Challenger Customer, and The Framemaking Sale, and the co-founder of A to B Insight, to discuss why decision confidence drives stronger outcomes than product features or supplier claims.

Alex Raymond sits down with Jennifer Pinter, a seasoned expert in account management software, to talk about what separates successful tech stacks from the ones that never gain traction.

Bad forecasts don’t just miss targets. They influence hiring plans, budgets, and boardroom confidence. Former Chief Revenue Officer Cliff Unger joins Alex Raymond to share how account managers can build the accuracy and credibility that drive both company growth and personal career impact.

Alex Raymond is joined by Carl Smith, the founder of The Bureau, to explore how the account management role has evolved from being a reactive liaison into one of the most strategic positions inside an agency.

Account managers who want a seat at the executive table need to master the art of growing revenue by owning client relationships, not just managing them. Alex Raymond and Mike Rapp, Chief Revenue Officer at IntelePeer, talk through what it takes to make that leap.

Kristy Devantier, the Managing Director at TaleWind Digital (formerly WorkerBee.TV), joins Alex Raymond for a conversation about what really changes when account managers have the right structure and clarity in their role.

Alex Raymond is joined by Craig Rosenberg, the Chief Platform Officer at Scale Venture Partners and the co-host of The Transaction, for a conversation about why account management continues to be under-resourced, undertrained, and underleveraged despite its direct impact on retention, expansion, and long-term revenue

Too many account managers confuse being liked with being effective and it’s costing them renewals, influence, and growth. Chad Horenfeldt, the VP of Customer Success at Siena AI and author of “The Strategic Customer Success Manager,” joins Alex Raymond to talk about the people-pleaser trap and how to break out of it.