In this episode of Revenue Insights, Guy Rubin sits down with Vanessa Metcalf, VP of Global Revenue Enablement at Showpad, to explore the evolving landscape of sales enablement. With over 18 years of experience spanning sales, enablement, and strategic operations, Vanessa offers invaluable insights on measuring enablement effectiveness, driving cross-functional alignment, and leveraging AI to transform go-to-market strategies.

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Vanessa shares how modern enablement is shifting from event-based training to continuous, data-driven development that directly impacts revenue outcomes. Vanessa breaks down her three-level framework for measuring enablement effectiveness—reaction, application, and revenue impact—and explains why enablement functions should report directly to revenue leadership to maintain strategic alignment. She also highlights how AI can automate administrative tasks, giving sellers more customer-facing time, and how data-driven approaches can optimize sales performance while creating sustainable behavioral change.

From building alignment between sales, marketing, and customer success teams to using AI-powered analytics to replicate top-performer behaviors, Vanessa offers practical strategies for revenue leaders seeking to enhance their enablement initiatives and drive measurable business outcomes. Her experience leading enablement at Docebo and now at a leading enablement software company gives her a unique perspective on how organizations can harness data, AI, and a customer-first mindset to achieve sustainable growth. This episode is a must-listen for leaders looking to modernize their enablement strategy and elevate revenue impact.

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 

[07:12] Three-Level Framework for Measuring Enablement Impact
Vanessa Metcalf introduces a practical framework for measuring enablement effectiveness through three distinct levels. The first level focuses on user reaction and adoption metrics like attendance and satisfaction, while the second level examines behavior change and knowledge application through call shadowing and trend analysis. The third level connects these metrics to tangible revenue KPIs that resonate with executives and board members. This framework helps enablement teams move beyond simple "smile and nod" metrics to demonstrate real business impact. For enablement leaders looking to prove their value, implementing this structured approach provides a clear path from program-level metrics to organizational impact.

[15:25] Automating Everything Except Core Selling
Showpad's approach focuses on automating administrative tasks while preserving the human elements of selling. Sales professionals typically spend less than two hours daily on customer-facing activities, with B-players particularly bogged down by administrative work. By leveraging technology to handle CRM updates and other routine tasks, sellers can focus more time on relationship building and value creation. This strategy helps increase customer face time from under 15% to nearly 50% for top performers. The approach has proven particularly effective in improving win rates and shortening sales cycles.

[27:44] AI's Evolution of Enablement Programs
Vanessa describes how AI is transforming traditional event-based enablement into continuous, data-driven development programs. The technology helps identify individual skill gaps and learning needs before they impact performance, moving away from one-size-fits-all approaches. AI-powered tools can analyze thousands of sales calls to identify specific areas where sellers excel or struggle with methodologies like MEDDPICC. This targeted approach allows enablement teams to provide personalized coaching and development at scale. The result is more efficient onboarding and continuous improvement processes that directly impact revenue metrics.

[39:10] Driving Change Through Data Visualization
The discussion reveals how transforming complex data into visual insights drives organizational buy-in and behavior change. When presented with clear visual evidence of how better qualification leads to fewer late-stage losses, both sales teams and executives are more likely to embrace new practices. Rather than forcing change through mandates, showing the direct correlation between specific behaviors and improved outcomes naturally motivates adoption. This data-driven approach has helped companies increase growth from single digits to 30% by making the benefits of change immediately apparent to all stakeholders.