Mastering Sales Leadership

About Mastering Sales Leadership

Mastering Sales Leadership is the B2B podcast for CROs, VP Sales, and revenue leaders who want sharper forecasts, smarter pipelines, and real talk about scaling sales organizations. Host Bill Kantor is the founder and CEO of Funnelcast and operator who has scaled sales teams past $200M in revenue. Every episode challenges conventional sales wisdom and replaces it with evidence-based frameworks, practical operating experience, and the honest stories behind what works (and what doesn't). Subscribe if you're serious about revenue and tired of forecasts that just report the obvious. 🔗 Learn more: funnelcast.com

Publisher

Bill Kantor

Category

business

Language

en

Explicit

No

First episode

10 Jul 2026

Latest episode

2 Nov 2026

Latest episodes

9 episodes in the feed.

1. 

   2 Nov 2026

   How to Build the Next Generation of Sales Leaders

   Great sales leaders don’t just build successful teams. They develop people who can eventually outperform them. Bill Kantor sits down with Tim O’Neil, Chief Revenue Officer at Matillion, four-time CRO, and creator of Pavilion’s CRO School. Tim shares lessons from scaling Alation from roughly $30 million to $160 million in three years and explains why developing future leaders matters more than personal recognition. Key Discussion Points 02:20 – Why Great Leaders Focus on Developing Others 04:30 – Hiring People Who Are Better Than You 07:30 – Finding the Right Mentor and Shared Values 12:40 – Why Solving Problems Beats Asking for Promotions 15:00 – How to Ask Your Manager to Coach You 18:30 – Building a Five-Year Career Roadmap 23:30 – Recognizing and Avoiding Organizational Toxicity 25:30 – Separating Facts from Opinions in Annual Planning 30:00 – Tim’s Journey Into Sales Leadership 34:30 – Negotiation Lessons From a Green Beret 35:30 – The “Tens and Ones” Framework for Win-Win Deals 39:30 – Connecting With Tim and Learning About Matillion Tim also shares a powerful negotiation framework he learned from Paul Weinman, a Green Beret and experienced contract negotiator who survived two plane hijackings. His approach reveals why the best negotiators focus on understanding what matters most to both sides. 👍 Like the epsiode if you found a useful leadership lesson.🔔 Subscribe for more conversations about sales leadership, revenue growth, and building high-performance teams.💬 Share your biggest takeaway in the comments. #MasteringSalesLeadership #SalesLeadership #RevenueLeadership #CRO #B2BSales #LeadershipDevelopment #Negotiation #Matillion

2. 

   19 Oct 2026

   How a RevOps Background Creates a Top-Performing CRO

   How does stepping into the CRO seat from Revenue Operations—rather than direct sales—change the way you scale a business? In this episode of Mastering Sales Leadership, host Bill Kantor sits down with Ryan Milligan, CRO at QuotaPath. Ryan shares how transitioning from RevOps to CRO shapes a quantitative, system-driven approach to durable revenue growth, sales team productivity, and compensation design. He reveals why headcount-driven scaling is dead, how to build predictive retention models based on usage data, and how incentive structures drive multi-year relationships. Key Discussion Points 00:02:00—Defining Durable Growth & The RevOps-to-CRO Transition 00:06:04—Transitioning from RevOps to Sales Leadership 00:08:15—Leading Sellers Without Ever Carrying a Quota 00:11:04—Why Headcount-Driven Sales Scaling is Dead 00:14:15—Centralizing Sales, Marketing, and CS to Avoid Friction 00:16:30—Bow-Tie Diagnostics: Market Problem vs. People Problem 00:24:30—Leveraging AI for Context Sharing & Automated Business Cases 00:31:00—Predictive Retention Modeling & Rep Engagement 00:35:00—Reconciling Board Expectations with Realistic Bottoms-Up Plans 00:37:01—From The New York Times Crosswords to CRO 00:42:30—How Comp Plans Actively Shape Revenue Want to build a predictable, scalable revenue engine for your sales organization? Watch the full conversation to learn the exact frameworks Ryan uses to align sales, marketing, and CS while maximizing per-rep efficiency. Don't forget to: 👍 Like this video 🔔 Subscribe for more authentic conversations 💬 Comment with your biggest takeaway 🔗 Share with someone who needs to hear this #SalesLeadership #RevOps #CRO #B2BSales #QuotaPath #SalesForecasting #CompPlans #MasteringSalesLeadership

3. 

   5 Oct 2026

   From Growth at All Costs to Profitable Scale

   What does it take to build a predictable, scalable revenue organization across changing market dynamics? Bill Kantor sits down with Mark Rosenthal to explore how sales leaders manage board dynamics, burn rates, and capital strategy under pressure. Mark also shares lessons from his experience building revenue organizations from $1M to over $100M. He also talks about managing board expectations across different ownership structures. And talks about how to  implement the core systems needed to guide sales teams through transition. Key Discussion Points 02:00—Venture Capital Dynamics & Growth at All Costs 08:30—Managing Capital Strategy, Capacity, & Burn Rates 11:00—Hiring Discipline: Why Bad Hires Cost More Than No Hires 15:00—Navigating Family Office Ownership & Board Governance 27:00—Private Equity Partnerships & Operating Frameworks 31:00—From Radio Ad IC to Strategic CRO 34:00—IC vs. CRO Mindset & Top-Line Stewardship 41:00—Ground-Level Leadership & The Factory Floor Approach 50:00—The 5 Ts Framework for Turnarounds & Transition If you're building a revenue organization for the next stage of growth, this conversation offers practical lessons on creating the systems, discipline, and leadership needed to scale. 👍 Like this episode🔔 Subscribe for more authentic conversations💬 Comment with your biggest takeaway📤 Share it with someone who needs to hear it #MasteringSalesLeadership #SalesLeadership #RevenueLeadership #CRO #RevOps #B2BSales #GTM #Forecasting #Leadership

4. 

   22 Sept 2026

   From Product-Market Fit to Go-to-Market Fit

   What does it take to build a predictable, scalable revenue organization? Bill Kantor sits down with Leor Teichmann to explore how AI is changing sales execution, deal management, and the role of the modern CRO. Leor also shares lessons from his experience building revenue organizations, managing board expectations, and creating the systems needed to turn growth into something more predictable and repeatable. Key Discussion Points 02:00—AI and Deal Health 09:00—Revenue Operating Cadence 18:00—AI-Powered Meeting Preparation 25:00—Building the Right GTM System 27:00—Product-Market Fit vs. Go-to-Market Fit 29:00—Board Expectations and Predictable Revenue 32:00—The Evolving CRO Role 35:00—Systems Thinking in Revenue Leadership 41:00—Leor's Journey Into Sales Leadership If you're building a revenue organization for the next stage of growth, this conversation offers practical lessons on creating the systems, discipline, and leadership needed to scale. Don't forget to: 👍 Like this episode if you find it insightful 🔔 Subscribe for more authentic conversations 💬 Comment with your biggest takeaway 📤 Share it with someone who needs to hear it #MasteringSalesLeadership #SalesLeadership #RevenueLeadership #CRO #RevOps #B2BSales #GTM #AI #Leadership

5. 

   7 Sept 2026

   The Power of No

   What does it really take to transform a sales organization? Bill Kantor sits down with Per Caroe to unpack how he helped Netcore increase its average deal size by 10X. Per shares what he learned about qualifying opportunities, improving lead quality, changing the ideal customer profile, building outbound discipline, and turning ambitious revenue targets into achievable goals. He also draws on his experience at IBM and across his sales career to share practical lessons on leadership, accountability, and building sales teams that perform consistently. Key Discussion Points 02:00 – Transforming Netcore's sales organization08:00 – Rethinking the sales approach15:00 – Improving lead quality and deal size20:00 – Building a disciplined outbound process30:00 – How experience changes the way you sell40:00 – Expanding beyond the existing ICP48:00 – Breaking down big revenue targets52:00 – Creating consistency in sales58:00 – The power of listening Watch the full episode to hear Per's lessons on building a stronger, more focused sales organization. 👍 Like this video🔔 Subscribe for more authentic conversations💬 Comment with your biggest takeaway📤 Share it with someone who needs to hear it #Funnelcast #SalesLeadership #B2BSales #SalesStrategy #SalesManagement #Leadership

6. 

   24 Aug 2026

   Stop Selling and Start Educating: Marc Friend on Sales Transformation

   Selling isn't always the answer. Marc Friend, CEO of Sift, explains why the best sales teams focus on education, disciplined execution, and earning customer trust. He shares practical lessons on transforming sales organizations, improving alignment, and building sustainable growth. Whether you lead sales, RevOps, or an entire business, you'll find actionable insights throughout this conversation. Key Discussion Points 00:00 - Introduction and Marc's leadership journey02:03 - From engineer to CEO04:17 - The three types of selling09:23 - Building a disciplined sales process12:08 - Why education beats selling13:08 - Leading business transformation16:47 - Communication drives alignment20:03 - Setting achievable growth plans26:24 - Creating sustainable growth31:10 - GFOC: Get in Front of Customers If this conversation challenged your thinking: 👍 Like this video to support more conversations with revenue leaders. 🔔 Subscribe for practical insights on sales leadership and forecasting. 💬 Comment with your biggest takeaway. 📤 Share this with someone leading a growing sales team. #MasteringSalesLeadership #SalesLeadership #SalesTransformation #RevenueLeadership #B2BSales #CustomerSuccess #GoToMarket #Leadership #Podcast

7. 

   10 Aug 2026

   Transform a Sales Organization Without Breaking It

   Leading one major transformation is difficult. Leading three at the same time is another challenge entirely. In this episode of Mastering Sales Leadership, Bill Kantor speaks with Luis Brito, CRO of ALLPLAN, about leading simultaneous business model, commercial, and sales transformations. Luis shares practical lessons on moving from perpetual licensing to subscriptions, redesigning sales organizations, aligning incentives, and leading teams through uncertainty. Key Discussion Points 01:58 The three simultaneous transformations 03:37 Why subscription changes everything 07:28 Building the transition strategy 13:09 Creating a global commercial organization 18:45 Redesigning the sales model 25:09 Lessons learned leading transformation 39:20 Leadership principles that build commitment If you're responsible for forecasting, scaling revenue, or leading organizational change, this conversation offers practical insights you can apply immediately. If this conversation resonates with you: 👍 Like this episode. 🔔 Subscribe for more conversations with today's top B2B revenue leaders. 💬 Share the biggest lesson you've learned about leading change. 📤 Share this episode with someone responsible for scaling a sales organization. #MasteringSalesLeadership #SalesLeadership #RevenueLeadership #CRO #SalesTransformation #RevenueOperations #CustomerSuccess #Leadership

8. 

   27 Jul 2026

   Why Most Sales Forecasts Fail (And What Great Revenue Leaders Do Instead)

   What if the sales forecasting methods we've accepted for years are actually limiting growth? In the first episode of Mastering Sales Leadership, Bill Kantor shares why he launched the podcast, the forecasting myths he believes hold sales teams back, and why better decisions—not bigger pipelines—drive better results. If you're a CRO, sales leader, RevOps executive, or anyone responsible for predictable growth, this conversation will challenge how you think about forecasting and sales performance. Key Discussion Points 00:00:57—Why this podcast exists 00:02—The problem with traditional forecasting 00:03—Why bigger pipelines aren't better 00:06—What you'll learn from future guests 00:10—Can leaders share their competitive advantage? 00:19—People buy for their reasons—not yours 00:25—Why Funnelcast takes a contrarian approach 00:27—Forecast accuracy vs. revenue growth 00:36—Bill's journey into sales analytics 00:48—Where to follow the podcast If you're responsible for forecasting revenue, managing growth, or leading a sales organization, this podcast is built for you. Don't forget to:👍 Like this video if it challenged your thinking.🔔 Subscribe for more conversations with top revenue leaders.💬 Comment with your biggest takeaway.🔗 Share this with another sales leader. #SalesLeadership #SalesForecasting #RevOps #RevenueOperations #B2BSales #RevenueGrowth #Leadership #MasteringSalesLeadership

9. 

   10 Jul 2026

   Let's Talk About the Numbers that the Board Doesn't See

   Every growth company sets a number. Someone has to own it. Behind every "aggressive growth target" is a sales leader making impossible calls in real time with a board watching, a team depending on them, and no guarantee the math will work out. Some quarters they nail it. Some quarters they don't. Almost no one talks about what that actually feels like, or what it takes to lead through it. This show is a series of honest conversations with the people who live inside that pressure—CROs, sales leaders, RevOps and finance leaders—about the moments that shaped how they lead. Not case studies. Not frameworks. Just what's actually true about leading revenue, told by the people who've done it. Because the number is never really about the number. It's about who you become chasing it. Tune in with Bill Kantor to learn more about mastering sales leadership and more. #SalesLeadership #RevenueLeadership #CRO #RevOps #B2BSales #GTM #NewPodcast #BusinessPodcast #SalesPodcast #LeadershipPodcast

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