The Revenue Dilemma

Tony Capasso
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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 obvious and solve the real problems blocking your next wave of growth, this podcast is for you.

Episodes

  1. Mar 5

    #6: Breakthrough Brief: AI Isn’t Replacing Your Sales Team (And It Shouldn’t) with Matt Dornfeld

    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 infrastructure, this conversation explores what actually drives revenue growth — and why orchestration, not automation alone, may be the real AI opportunity in sales. If you’re leading a revenue team, building AI workflows, or trying to figure out where to place your bets, this episode brings clarity to the noise. About: Matt Dornfeld is a senior technology leader focused on AI, automation, and strategic partnerships in ecommerce and enterprise tech. He currently serves as Senior Director, Global AI Go-To-Market (GTM) across BigCommerce, Feedonomics and Makeswift, where he drives unified AI-led commercial strategy and revenue enablement. Previously, he led global technology partnerships at Feedonomics, building integrations and alliances with major commerce platforms including Amazon, Google, Meta, Microsoft and TikTok. Matt helps companies scale smarter with AI and automation while shaping modern ecommerce growth and partner ecosystems.  Matt on Linkedin Tony Capasso on ⁠Linkedin⁠ OnProfit ⁠Website⁠ Revenue Dilemma ⁠Website⁠

    9 min

  2. Feb 19

    #5: The Hidden Drag on Growth No One’s Naming with Allie Garfinkle

    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 that “everyone has a grand opera inside of them” — and unpacks how deep listening, presence, and thoughtfully-applied tension can unlock truth in interviews, leadership, and company-building. You’ll hear: Why post-Covid behavior changes are still distorting growth and hiring What’s actually broken in talent assessment (and why old “signals” don’t work) Why the “AI bubble” take is lazy — and the better question to ask Customer devotion as the real moat (and the red flag question she always asks) Why ARR can mislead — and how to interrogate metrics that matter (hint: slope) About: Allie Garfinkle is a senior writer at Fortune, covering venture capital and startups. She writes Fortune’s weekday dealmaking newsletter Term Sheet, hosts the Term Sheet Podcast, and co-chairs Fortune Brainstorm, the community and event series behind Fortune’s Brainstorm gatherings. She has previously covered Big Tech at Yahoo Finance (print and broadcast), began her career across outlets including Financial Times Specialist / The Deal and Forbes, and has contributed to business documentary production for PBS Frontline. Allie on Linkedin Tony Capasso on ⁠Linkedin⁠ OnProfit ⁠Website⁠ Revenue Dilemma ⁠Website⁠ The Revenue Dilemma on ⁠Linkedin⁠ The Revenue Dilemma on ⁠Youtube⁠, ⁠Spotify⁠, ⁠Apple

    41 min

  3. Feb 12

    #4: Love Over Fear: Leading Through the Biggest Tech Shift with Brett A. Hurt

    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 explains why enterprises are stuck in fear and inertia, how to rebuild customer acquisition for an agent-driven world, and why “leading through love” is a competitive advantage in periods of massive change. You’ll hear stories and frameworks — including: Why the web browser era is ending and “agents acting on your behalf” are beginningThe new SEO race: how brands get discovered when humans aren’t clickingWhy GenAI adoption stalls in the enterprise (fear, incentives, governance, and change resistance)A practical model for creating internal pull: identifying “builders,” removing bottlenecks, and automating low-leverage workHow AI can drive margin expansion and unlock more creativity in teams — if leaders push for capability, not complianceWhat personalization should look like now (and why most outreach is getting worse, not better)Brett’s bigger thesis: why our biggest risk isn’t the tech — it’s the fear-based mindset that controls how we use itIt’s a candid conversation for founders, operators, revenue leaders, and executives trying to stay relevant — and win — as the customer journey becomes automated. About Brett Hurt: Brett A. Hurt is a serial entrepreneur, investor, and author based in Austin. He founded Coremetrics (web analytics), acquired by IBM in 2010, and co-founded Bazaarvoice, which he led as CEO through its 2012 IPO and subsequent growth. He later co-founded and served as CEO of data.world (data catalog and governance), which ServiceNow agreed to acquire in 2025. Brett is the creator of The Entrepreneur’s Essentials and directs proceeds to support female entrepreneurs at UT Austin’s Kendra Scott Women’s Entrepreneurial Leadership Institute. He also hosts the Love Conquers Fear podcast and leads the Love Conquers Fear holding company focused on technology, consciousness, and the “Age of Abundance for All.” Brett A. Hurt on Linkedin Brett’s podcast: Love Conquers Fear Tony Capasso on ⁠Linkedin⁠ OnProfit ⁠Website⁠ Revenue Dilemma ⁠Website⁠ The Revenue Dilemma on ⁠Linkedin⁠ The Revenue Dilemma on ⁠Youtube⁠, ⁠Spotify⁠, ⁠Apple

    1h 15m

  4. Jan 28

    #3: The Revenue Algorithm: How Great Operators Build Enterprise Value in Software with Sam Monti

    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 — and leadership roles at companies like Epicor, Lithium/WP Engine, and Vista-backed platforms — Sam breaks down his simple but powerful “revenue algorithm,” explains why most companies leave millions on the table, and shares hard-earned lessons from more than 30 acquisitions. You’ll hear stories from his time inside PE portfolio companies and public enterprises — including: Why net revenue retention is the single most important growth lever in software businessesHow to design commission plans that actually maximize enterprise valueThe “Moneyball” approach to acquisitions — and why smaller, strategic targets often outperform splashy dealsWhat most buyers get wrong about culture integration after an acquisitionWhen to build vs. buy product capabilities — and how to avoid costly engineering detoursWhy great boards, meritocratic cultures, and operational rigor outperform flashy mission statementsHow Sam thinks about legacy, board service, and teaching the next generation of operatorsIt’s a candid, tactical conversation for revenue leaders, CFOs, founders, and private-equity operators focused on bending the growth curve — without overcomplicating what really drives value. About Sam: Sam Monti is a veteran software operator and executive with decades of experience scaling private-equity-backed and public companies. He has held senior leadership roles at Epicor, Lithium/WP Engine, and multiple Vista-backed platforms, and has led or supported more than 30 acquisitions across SaaS, MarTech, supply chain, industrial, and legal technology. Known for his practical, value-creation mindset, Sam focuses on improving net revenue retention, sharpening go-to-market execution, and building durable operating cultures. Sam Monti on Linkedin Tony Capasso on ⁠Linkedin⁠ OnProfit ⁠Website⁠ Revenue Dilemma ⁠Website⁠ The Revenue Dilemma on ⁠Linkedin⁠ The Revenue Dilemma on ⁠Youtube⁠, ⁠Spotify⁠, ⁠Apple

    1h 29m

  5. Jan 21

    #2: The Hidden Signals That Drive Growth with Jim Stoneham

    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 explore where AI is genuinely adding leverage today, how to avoid waiting for “perfect” data, and why focus — not scale — is often the missing ingredient for founders and revenue leaders. You’ll hear stories from his work across product, growth, and go-to-market at companies like Yahoo, New Relic, Stripe, and SignalFire — including: Why product-led growth fails without human judgment — and where people still create the biggest leverage.How trigger-based product signals outperform generic funnels in sales and marketing.What most teams get wrong about data readiness — and why waiting for “perfect” data slows growth.Where AI is actually useful today in GTM — and where it creates noise instead of impact.Why focus beats scale when building durable go-to-market systems. About Jim: Jim Stoneham is a Partner at SignalFire, where he works closely with founders on go-to-market strategy, product-led growth, and scaling revenue organizations. Prior to SignalFire, Jim held senior leadership roles at companies including New Relic, Stripe, and Yahoo, where he helped build and scale growth, product, and GTM teams through periods of rapid expansion. With a background spanning product, growth, and sales, Jim brings a deeply cross-functional perspective on how modern SaaS companies succeed — combining data, human insight, and disciplined focus. Jim Stoneham on Linkedin Tony Capasso on ⁠Linkedin⁠ OnProfit ⁠Website⁠ Revenue Dilemma ⁠Website⁠ The Revenue Dilemma on ⁠Linkedin⁠ The Revenue Dilemma on ⁠Youtube⁠, ⁠Spotify⁠, ⁠Apple

    59 min

  6. Jan 13

    #1: Making It Easier to Buy: The Growth Lever No One Invests In with Carla Piñeyro Sublett

    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 outdated, fear-based, siloed ways companies operate and explains how creating psychological safety, real inquiry, and customer-first thinking unlocks performance and growth. You’ll hear stories from her time leading global teams at companies like IBM, National Instruments (NI), Rackspace, and Dell — including: Why fear and pressure don’t drive growth — and what does.How making it easy for customers to buy is one of the most overlooked levers for revenue.What real cross-functional alignment looks like in high-growth companies.How even big, well-meaning organizations can fail by focusing on activity over impact.The vital link between personal wellbeing, emotional awareness, and leadership effectiveness.Carla also shares perspectives on modern leadership, the importance of self-inquiry, and how leaders can break free from traditional norms to create healthier, more productive workplaces. About Carla: Carla Piñeyro Sublett is a former Fortune 50 marketing and growth executive turned leadership coach and organizational transformation expert. She has led global teams at IBM, Dell, Rackspace, and National Instruments, driving brand reinvention, go-to-market strategy, and sustainable growth. Today, Carla helps leaders move beyond fear-based, siloed cultures to build organizations rooted in trust, inquiry, and real customer impact. Carla’s podcast lets go there Carla’s Website Tony Capasso on ⁠Linkedin⁠ OnProfit ⁠Website⁠ Revenue Dilemma ⁠Website⁠ The Revenue Dilemma on ⁠Linkedin⁠ The Revenue Dilemma on ⁠Youtube⁠, ⁠Spotify⁠, ⁠Apple

    1h 10m

  7. Season 1 Trailer

    Trailer: Welcome to the Revenue Dilemma

    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 obvious and solve the real problems blocking your next wave of growth, this podcast is for you. Tony Capasso on Linkedin OnProfit Website Revenue Dilemma Website The Revenue Dilemma on Linkedin The Revenue Dilemma on Youtube, Spotify, Apple

    1 min

Trailer

About

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 obvious and solve the real problems blocking your next wave of growth, this podcast is for you.

Information

  • Creator
    Tony Capasso
  • Years Active
    2K
  • Episodes
    7
  • Rating
    Clean
  • Copyright
    © Tony Capasso
  • Show Website
    The Revenue Dilemma