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

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.

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.

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.

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.

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.