Architecting Scalable, AI-Safe Revenue Systems with Pranav Lal, Head of Business Technology at Gusto

In this episode, Jeff is joined by Franco Anzini, a GTM operations executive who has helped scale multiple SaaS companies from $10M to $250M ARR and led organisations through IPO and acquisition.Franco shares what RevOps actually looks like at different stages of growth, and how the role evolves as companies scale. From building the operational foundations in early growth, to creating forecasting discipline before IPO, he explains the systems, data infrastructure, and decision-making frameworks that allow revenue teams to grow sustainably.They also discuss the shift from systems thinking to business impact, the rise of GTM engineering, and why AI initiatives often fail without clean, centralised data.

In this episode, Jeff sits down with Guy Rayer, VP of Revenue Operations at Kontakt.io, to explore how RevOps is evolving in a world of AI, limited TAM, and complex healthcare buying cycles.Guy shares how operating in a concentrated healthcare market, just 300 target health systems representing 80% of the opportunity, fundamentally changes go-to-market strategy. Instead of volume-based outbound, his team leans into depth: account-based execution, persona mapping, proximity strategy, and face-to-face influence at industry events like HIMSS and ViVE.

In this episode, Jeff sits down with Jaap Westrick, Founder of Modern Revenue, to explore the hidden disconnect between finance and go-to-market team, and why compensation plans are often blamed for problems they didn’t create.Drawing on his background in finance and advisory work with 30+ companies, Jaap explains why CRO–CFO misalignment stems from fundamentally different training, incentives, and languages. They unpack why comp plans are usually a symptom of deeper strategic issues - from poor planning cycles and unclear definitions to flawed capacity models and disconnected data strategies.

In this episode, Jeff sits down with Pranav Lal, Head of Business Technology at Gusto, to unpack what it really means to build a commerce engine, not just a tech stack.Drawing on experience from high-growth journeys at Slack, Eventbrite, and Ethos Life, Pav shares hard-won lessons on lead-to-cash architecture, IPO readiness, SOX compliance, and designing systems that scale without drowning in tech debt.

Clark Dixon, VP of Revenue Operations at EverDriven, joins the show to discuss how revenue architecture creates clarity, alignment, and focus across go-to-market teams.EverDriven is a mission-driven company providing modern transportation solutions for K–12 students with unique needs, including those experiencing homelessness or requiring specialised support. Clark shares how the bowtie data model became a powerful unifying framework in his previous roles, transforming disconnected funnels into a single, measurable revenue system.

How do you grow faster while creating fewer opportunities? Alex Kusters explains how Impact Networking redefined its ICP, built a formulaic targeting model, and embraced signal-based selling to drive 114% growth in net-new logos. A masterclass in modern RevOps, mid-market positioning, and building systems people actually want to use.

Jordan Crawford explains the Permissionless Value Prop, a way of combining internal and external data to create outreach that earns attention.- Why most AI SDR tools produce identical messages- The limits of firmographic ICPs- How to define a “paying qualified segment”- Vertical vs. horizontal GTM trade-offs- Where RevOps should start with AI

In this episode, Jeff is joined by Stuart Watson, Head of Revenue Operations at ResolveAI, to unpack how modern AI workflows are changing what’s possible in RevOps.From deploying hundreds of autonomous agents to clean and qualify messy account data, to using Claude Code to cut territories, build internal tools, and replace legacy dashboards, Stuart shares real-world examples of how AI can close data gaps instead of waiting for them to be fixed.The conversation explores why “AI-ready data” doesn’t mean perfect data, how agentic workflows are turning RevOps leaders into digital workforce managers, and what skills will matter most as AI becomes embedded in go-to-market operations.

In this episode, Jeff talks with Pedrum Khosravi, Senior Director of Growth Operations at Paytient, about how to connect GTM work directly to business outcomes. They dig into building a usable revenue model, mapping initiatives to the right KPIs, using AI for enrichment and handoffs in tools like HubSpot, and why RevOps leaders should take more high-upside risks to truly move the needle.

In this episode, Jeff sits down with Colin Brown, VP of Revenue Operations at DDN, to unpack what AI adoption actually looks like in go-to-market teams. From distinguishing AI-supported habits vs. AI-enabled processes to evaluating build vs. buy, Colin shares candid lessons, the tooling he trusts, why custom workflows matter, and the real challenges of change management. A pragmatic, no-fluff look at where AI drives genuine productivity, and where it doesn’t.