In this episode of Revenue Insights, host Guy Rubin, CEO of Ebsta, sits down with Ian Wessel, Vice President of Revenue Operations and Strategy at Monta, to explore the strategic evolution of RevOps and its impact on business transformation. With over 17 years of experience across industries like real estate, public accounting, Salesforce, and Intercom, Ian shares how revenue operations can drive measurable outcomes through data, enablement, and cross-functional alignment.

From proving RevOps ROI to implementing consistent deal review processes and optimizing sales enablement, Ian breaks down what it takes to connect operational work to strategic business goals. He dives into frameworks like “Hug vs. Handshake” for seamless team transitions, the role of AI in sales efficiency, and the importance of maintaining data quality in an evolving tech landscape.

Whether you're a RevOps leader aiming to demonstrate impact or a business executive focused on GTM performance, this episode is packed with practical insights to help you scale revenue operations effectively.

Ebsta is a revenue intelligence platform that helps B2B sales teams drive predictable growth by leveraging relationship and activity data. With real-time insights into pipeline health and sales performance, Ebsta empowers leaders to make informed, data-backed decisions. Find out more: https://www.ebsta.com/get-a-demo

Data-Driven Deal Discovery Requirements
Ian shares a critical insight about enterprise deals requiring at least 5 hours of thorough discovery to have any chance of closing successfully. He explains that surface-level qualification using standard frameworks like MEDDPIC isn't enough for complex, high-value opportunities in the $10-20M range. Rather than relying on lightweight discovery sessions of 1-2 hours, top performers dig deep into technical requirements and business needs through extended discovery. By visualizing this data on deal size and discovery time correlation, RevOps teams can make a compelling case to leadership about the importance of proper qualification. The clear relationship between discovery investment and win rates provides an evidence-based approach to improving sales effectiveness.

The "Hug vs Handshake" Handoff Model
Ian introduces a powerful framework for improving coordination between pre-sales and post-sales teams to prevent customer churn. He emphasizes that the handoff between teams should be a "hug, not a handshake" - meaning deeper engagement and knowledge transfer rather than basic information sharing. This approach helps prevent accounts from becoming problematic immediately after closing due to misaligned expectations or missing implementation requirements. Regular deal reviews with both pre and post-sales teams present allow for early identification of potential issues. The model creates shared accountability across the entire customer journey rather than siloed responsibility.

Proving RevOps Value Through Closed Loop Reporting
Ian outlines a systematic approach to demonstrating RevOps' strategic value by connecting initiatives to measurable business outcomes. He explains that while RevOps teams often receive praise, quantifying their impact is crucial, especially when headcount decisions are being made. The key is establishing clear KPIs aligned to company goals, mapping specific RevOps activities to those metrics, and religiously tracking progress. By closing the feedback loop through consistent reporting on results versus targets, RevOps can prove its worth beyond tactical execution. This data-driven approach helps secure RevOps' seat at the strategic table.

Balancing AI Automation with Human Expertise
Ian provides an important perspective on the evolving role of AI in revenue operations, cautioning against over-reliance on automation. While acknowledging AI's value, he emphasizes that many core RevOps functions still require deep analysis and human judgment to identify root causes that AI can only surface. The key is finding the right balance where AI handles routine tasks while RevOps professionals focus on strategic problem-solving. This hybrid approach allows teams to leverage technology while maintaining the strategic thinking that drives business transformation.