Revenue Insights Podcast

Eleanor O'Neill: The Hidden Revenue Engine You're Ignoring (Hint: It's Your Customers) 08.05.2026 35мин

In this episode of the Revenue Insights Podcast, host Guy Rubin, Ebsta founder and MD of Revenue Intelligence at Fullcast, sits down with Eleanor O'Neill, Chief Revenue Officer at Mont, a company that operates at the intersection of infrastructure, sustainability, and next-generation software. Eleanor started as an engineer, moved through CIO and CTO roles, led customer organizations and now sits at the center of revenue strategy. This unique journey provided a radically different perspective on what it actually takes to build a modern revenue engine. And here are a few key points from what she has experienced: –If your revenue strategy doesn't start with the customer, your pipeline is already at risk. –If AI isn't embedded into your workflows, you're already behind. –If your RevOps team isn't driving decisions, your CRO is flying blind. Throughout the conversation, Eleanor makes it clear that revenue growth is no longer about activity. It's about alignment, insight, and execution at scale. What You Will Learn From This Podcast Why the future CRO is less "deal closer" and more data-driven orchestrator How Eleanor's technical background reshapes accountability across teams Why the best pipelines don't start with net-new leads—they start with happy customers How customer success fuels expansion, references, and lower churn Why top-performing teams qualify out early and win more because of it The hidden cost of "hope-driven forecasting" How Mont uses AI to analyze thousands of hours of calls and automate reporting Why AI is shifting teams from execution to interpretation and strategy If you're a CRO, RevOps leader, or GTM executive trying to make sense of AI, pipeline quality, and the evolving revenue stack, this conversation will challenge how you think about revenue growth.

Tyler Will: The Death of Seat-Based SaaS: Why AI Changes Everything 01.05.2026 35мин

In this episode of the Revenue Insights Podcast, Guy Rubin, Ebsta founder, MD of Revenue Insights at Fullcast, and host of the Revenue Insights podcast, talks with Tyler Will, VP of Revenue Operations at Intercom, to discuss one of the most aggressive AI pivots in SaaS. Tyler has led revenue operations through global scale at Bain, LinkedIn, and now Intercom where he's helping transform the company into an AI-first customer experience platform powered by Fin, their AI agent launched shortly after ChatGPT. "If you're not ahead of the curve, you don't get to iterate your way into AI," Tyler said. "You have to rip up your entire sales playbook and start over." But what actually breaks when you operationalize AI inside a revenue organization. More importantly, what does it take to rebuild it? We're entering a world where: 80%+ of customer interactions can be handled by AI Sales teams are flooded with more leads—but not more revenue And RevOps is the only function positioned to connect data, process, and execution This episode is your roadmap for navigating that shift. In this episode, learn: Why most companies fail to monetize AI—even when adoption is high How Intercom flipped from "AI as an add-on" to AI as the core product The real role of RevOps in an AI-first business (hint: it's not reporting) Why incentive design—not technology—is the unlock for AI adoption How to rebuild your sales playbook from scratch for agentic workflows The shift from "seat-based SaaS" to outcome-based AI engagement models Why post-sales is now the most complex—and valuable—motion in GTM How AI is reshaping SDR, CSM, and sales engineering roles in real time As Tyler Will makes clear, AI doesn't politely integrate into your existing GTM motion—it stress-tests it. It exposes misaligned incentives, outdated roles, and fragile processes that were never built for autonomous execution. The shift from seat-based SaaS to outcome-based AI is here. And the companies that win won't be the ones experimenting on the edges. They'll be the ones willing to rebuild with RevOps as the core for a strategic engine driving alignment between data, behavior, and growth. Tune in to this episode of the Revenue Insights Podcast with Guy Rubin and Tyler Will to hear what it actually takes to operationalize AI at scale and why the future of revenue belongs to the teams bold enough to start over.

Peter Grant: The GTM Reset No One Is Prepared For 17.04.2026 35мин

In this episode of the Revenue Insights Podcast, host Guy Rubin, Ebsta Founder, MD of Revenue Insights at Fullcast, sits down with Peter Grant, Chief Revenue Officer at You.com, to discuss what it really takes to scale in an AI-first world and why most revenue teams are quietly falling behind. Peter has built his career at the exact moment that industries shift—joining Siebel Systems, Salesforce, and C3.ai before they became category leaders. Now, he's at the forefront of the next transformation and his perspective is that the release of ChatGPT reset GTM entirely. For instance, by layering tools like Claude and Gong into their workflows, leaders can: Break down every customer conversation Track deal progression against reality—not CRM guesswork Identify risk before it shows up in the forecast At You.com, the focus sits squarely on indexed AI agents that answer complex, domain-specific questions. As Peter points out, this is the shift from information retrieval to decision enablement. The 4 Signals That Separate Real AI Companies from Hype Peter breaks down the framework he uses to evaluate AI companies before they break out: People: Can this team actually deliver? Market: Is the pain real or manufactured? Product: Does it create immediate, accurate value? Timing: Can they move faster than the market? Miss one and the whole thing collapses. What You'll Learn in this Episode Guy and Peter explore why: –AI is creating a "performance divide" in Sales –Why SaaS pricing is being rewritten in real time –Why seat-based pricing is losing relevance. Why You Should Listen If you're a: CRO trying to scale in an AI-first market RevOps leader responsible for making AI actually work Founder navigating pricing, positioning, and product-market fit This episode will challenge how you think about growth.

Tera Gillen: Sustainable Growth, Revenue Retention & the Human Side of Sales 10.04.2026 25мин

In this episode of the Revenue Insights Podcast, host Guy Rubin sits down with Tera Gillen, Vice President of Global Operations at Atlantic Growth Solutions, for a deep, practical conversation on what sustainable growth really looks like in modern B2B organizations. With a career spanning leadership roles at Skillsoft, Docebo, and now Atlantic Growth Solutions, Tera brings a rare blend of operational rigor and human-centered leadership. Together, Guy and Tera explore how aligning people, process, and technology is the key to predictable growth—without burning out your teams or alienating your customers. From redefining ICP through the voice of the customer, to building retention engines driven by executive-level engagement, this episode is packed with real-world insights for sales leaders, RevOps professionals, and customer success teams navigating growth in an AI-driven world. Key takeaways: ✔ Growth starts with listening to your customers ✔ Retention is driven by engagement, not just usage ✔ Data matters—but context and storytelling matter more ✔ The best RevOps teams power the entire executive strategy ✔ Sustainable growth is built by empowering people, not exhausting them Whether you're a CRO, RevOps leader, sales manager, or founder, this conversation will challenge how you think about growth, retention, and leadership heading into 2026.

Mike Huffaker: The Hidden SaaS Opportunity Inside Dentistry 06.03.2026 34мин

In this episode of the Revenue Insights Podcast, host Guy Rubin, Ebsta founder and MD of Revenue Intelligence at Fullcast, sits down with Mike Huffaker, Chief Revenue Officer at Planet DDS and host of The Dental Economist Show. Mike's journey into SaaS leadership didn't start in technology. Instead, it started by selling high-end Italian shoes to retailers like Neiman Marcus and Nordstrom. But when he looked around Silicon Valley and realized tech was reshaping the world, he took a leap that would redefine his career. After breaking into SaaS through an early-stage startup, Mike quickly rose through the ranks building remote sales teams, opening multiple offices, and scaling organizations from scratch. Today, as CRO at Planet DDS, he leads a rapidly growing revenue organization that has helped scale the company from $12M ARR to more than $100M. In this conversation, Mike shares the leadership mindset that fueled that growth, why curiosity is the most underrated trait in sales, how listening deeply to customers creates category leadership, and why many assumptions about career ceilings in tech are simply wrong. If you're a sales leader, founder, or revenue operator, this episode reveals how great leaders turn curiosity into growth, build loyal customers, and scale SaaS companies in unexpected industries.

Why 52% of New Revenue Now Comes From Existing Customers | Ben O Mathuin 09.10.2025 38мин

In this episode, Ben O'Mathuin shares how to transform Customer Success from a retention function into a strategic revenue engine. Learn how to align Sales and CS, coach CSMs for commercial impact, and drive predictable growth from existing accounts.

This VP Grew Revenue from $15M to $45M Using These Sales Strategies | Mikey Abts 25.09.2025 40мин

Discover how Recast Software's VP of Sales, Mikey Abts, is redefining sales-generated opportunities. In this episode of Revenue Insights, learn how to move beyond traditional BDR models with freemium strategies, AI-driven qualification, and relationship-focused selling to drive consistent revenue growth. [The Revenue Insights Podcast is sponsored by Mailtrap. Try Mailtrap for free: https://l.rw.rw/revenue_insights_3]

Why 75% of Sales Deals Fail (And How AI Can Fix It) | Vanessa Metcalf 18.09.2025 44мин

Explore how Vanessa Metcalf, VP of Global Revenue Enablement at Showpad, joins host Guy Rubin on the Revenue Insights podcast to discuss leveraging data, AI, and strategic alignment to transform sales enablement, drive measurable revenue impact, and create sustainable behavioral change. [The Revenue Insights Podcast is sponsored by Mailtrap. Try Mailtrap for free: Mailtrap.io]

The AI Sales Revolution: Why B-Players Won't Survive the Next 3 Years | Daryl Weldon 02.09.2025 35мин

In this week's eisode of Revenue Insights, Adam Roberts sits down with Daryl Weldon, VP of Sales at Verisys, to discuss her journey from clinician to sales leader and the keys to building high-performing, trust-based teams in today's AI-driven sales landscape.

Why 69% of Workers Don't Engage & How Revenue Leaders Can Fix It | Greg Leos 14.08.2025 40мин

In this episode of Revenue Insights, Greg Leos, Payments Division Leader at Weave, unpacks the critical breakdown in employer-employee trust and its impact on revenue growth, talent retention, and workplace performance. Drawing on over two decades of global revenue leadership, he shares actionable strategies for building authentic cultures, balancing performance with respect, and creating environments where top performers thrive.

How High-Growth Companies Nail Sales Qualification 31.07.2025 9мин

Discover proven sales qualification strategies in this greatest hits episode of Revenue Insights. Learn how top revenue leaders implement MEDDIC and Acxiom frameworks to improve pipeline quality, drive adoption, and close bigger deals.

Why Only 1 in 5 Reps Hit Quota—And How Data-Driven Leaders Fix It | Dieter Heren 03.07.2025 34мин

In this episode of Revenue Insights, Adam Roberts chats with Popl VP of Sales Dieter Heren about evolving from RevOps to sales leadership, using AI without losing human connection, consolidating tech stacks, and building data-driven, efficient revenue teams.

How Pavilion Scaled to 10,000 Members—Without Traditional Marketing | Sam Jacobs 19.06.2025 42мин

In this episode of Revenue Insights, host Guy Rubin speaks with Sam Jacobs, Founder and CEO of Pavilion, about the evolving challenges of B2B sales and revenue leadership. Sam explains why the SaaS playbook is no longer effective, how AI is reshaping go-to-market strategies, and why customer retention is now the true growth driver. They dive into data-backed approaches for building resilient revenue teams, pushing back on unrealistic targets, and thriving in an increasingly volatile market.

Why Traditional Pipeline Management Is Dead with Kyle Morden 29.05.2025 44мин

In this episode of Revenue Insights, host Guy Rubin speaks with Kyle Morden, VP of Sales at HiHello, Inc., about how AI and data-driven strategies are transforming modern sales. Kyle shares why 44% of sales contacts never make it to CRM—and what that means for pipeline accuracy and team efficiency. They explore how sales leaders can strike the right balance between automation and authentic human connection to drive long-term customer relationships.

Why Channel Partners Drive 3X Higher Win Rates—The Hidden Data with Alex Rich 15.05.2025 34мин

In this episode of Revenue Insights, host Guy Rubin sits down with Alex Rich, VP of Sales North America at GitGuardian, to discuss how focused channel partnerships can drive scalable revenue. Alex shares his "Focus Partner Model," insights on avoiding channel conflict, and why well-supported partner managers can outperform individual reps. Perfect for sales leaders looking to turn partnerships into a core growth engine.

The Data-Driven Sales Turnaround: 37% Growth in Under 12 Months ft. Shianne Sampson 08.05.2025 34мин

In this episode of Revenue Insights, host Guy Rubin talks with Shianne Sampson, Global VP of Sales at Eventbrite, about turning around underperforming sales teams through data-driven leadership and culture-first coaching. Discover how side-by-side coaching, clear expectations, and tough personnel decisions can create a high-performance sales culture built for sustainable success.

Why Top Sales Leaders Get Coaching Wrong—And How an Olympian Fixes It with Matt Hemingway 17.04.2025 46мин

In this episode of Revenue Insights, host Guy Rubin talks with Matt Hemingway, VP of Sales & Operations at Axcient and Olympic silver medalist, about applying disciplined coaching and culture-first leadership to build high-performing sales teams. Learn how the SPAC framework, strategic hiring, and internal promotion drive sustainable revenue growth.

The Untold Truth of RevOps—How Only 20% of Teams Drive 80% of Impact with Ian Wessel 10.04.2025 38мин

In this episode of Revenue Insights, host Guy Rubin, CEO of Ebsta, sits down with Ian Wessel, VP of Revenue Operations and Strategy at Monta, to discuss how RevOps drives business transformation. Ian shares insights on proving ROI, aligning cross-functional teams, and leveraging data for strategic decision-making. With over 17 years of experience across companies like Salesforce and Intercom, he offers practical strategies for scaling revenue operations and connecting GTM execution to measurable outcomes.

How Top Performers Handle Objections 80% Earlier—And Win More Deals with Hervé Timsit 03.04.2025 41мин

In this episode of Revenue Insights, host Guy Rubin, CEO of Ebsta, sits down with Hervé Timsit, Chief Revenue Officer at EDB, to explore the evolving landscape of enterprise software sales. Hervé shares insights on leading global sales teams, implementing data-driven strategies, and the critical role of the MEDDIC methodology in modern sales processes. He also discusses how AI and analytics are reshaping sales qualification, customer engagement, and revenue optimization. With over 17 years of experience in enterprise software, Hervé provides actionable takeaways for sales leaders looking to scale their teams and drive growth in an increasingly competitive market.

Why Your ICP is Wrong—And How to Fix It with Dan Sylvester 27.03.2025 38мин

In this episode of Revenue Insights, host Adam Roberts, Sales Director at Ebsta, speaks with Dan Sylvester about the evolving dynamics of B2B sales and customer success. Dan shares insights on aligning value across teams, balancing automation with human engagement, and redefining ideal customer profiles for sustainable growth. With extensive experience in revenue leadership, he specializes in optimizing customer journeys, scaling high-value activities, and driving measurable outcomes. This episode offers key takeaways for revenue leaders looking to enhance sales efficiency, improve customer advocacy, and adopt smarter growth strategies.