The Revenue Dilemma

AI SDRs are everywhere — but are they actually working? In this episode, we unpack the growing hype around AI-driven outbound sales and why simply increasing activity won’t fix a broken pipeline. Instead of replacing humans, our guest argues for augmenting them — and explains why most organizations are solving the wrong problem. From market readiness and product-market fit to messaging and data in...

What if the biggest growth constraint in your business isn’t your product, pricing, or pipeline — but the unspoken shifts in how people work, buy, and build after Covid? In this episode of The Revenue Dilemma , Tony sits down with Allie Garfinkle (Fortune Senior Writer) for a masterclass in perspective from one of the sharpest pattern-recognizers in tech. The conversation starts with Allie’s idea...

In this episode, Brett A. Hurt joins us for a wide-ranging masterclass on what’s about to break in go-to-market — as AI agents begin to replace web browsers, rewrite “search,” and fundamentally change how companies reach customers. Drawing on decades building and scaling category-defining software companies — and most recently leading data.world through its acquisition by ServiceNow — Brett explai...

In this episode, Sam Monti joins us for a masterclass on building enterprise value in software businesses — from scaling recurring revenue and structuring sales compensation to executing disciplined M&A and shaping high-performance cultures inside private-equity-backed companies. Drawing on decades of operating experience across industrial, SaaS, MarTech, legal tech, and supply chain software...

In this episode, Jim Stoneham joins us to unpack what product-led growth really looks like in practice — and where human intervention still matters most. Drawing from his experience at New Relic, Stripe, Yahoo, and now SignalFire, Jim shares how deep product instrumentation, trigger-based engagement, and focused ICPs create outsized impact across sales, marketing, and customer success. We also exp...

In this episode, host  Tony  sits down with  Carla Piñeyro Sublett , a seasoned Fortune 50 marketing and go-to-market executive turned coach and organizational transformation leader. Carla pulls back the curtain on why the biggest barriers to growth in today’s organizations aren’t product, lead gen, or even competition —  they’re the way we lead people and define success . She challenges the outda...

What if you were leaving 20% of your revenue on the table? Hosted by a four-time CRO Tony Capasso, who has scaled growth-stage companies to $1B+, The Revenue Dilemma unpacks the hard truths behind revenue growth. The untapped opportunities, the invisible psychological roadblocks, and the real strategies that separate stalled companies from soaring ones. If you're ready to move beyond the obvio...