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.

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.

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.

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.

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.

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.

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]

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]

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.

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.