#219: Salesforce legend Phil Cleary on Why Sales Forecasts Are Breaking in 2026, and why Revenue Enablement Fails Without Commercial Architecture

Revenue leaders don’t trust their pipeline anymore.In this episode, we sit down with Phil Cleary – 20+ year Salesforce veteran and co-lead of the Revenue Enablement Society – to unpack what’s really happening inside revenue teams right now.We break down why forecasts are slipping, why pipeline feels fabricated, and why traditional sales training isn’t fixing behaviour.This is a deep dive into revenue enablement strategy at the leadership level.We cover:+ Why buyers are frozen (FOBO from FOMO)+ The 2x2 coaching model every sales leader should use+ Why “software with a service” is the future of SaaS+ How behaviour, identity, and mindset drive real adoption+ Why you are your calendarIf you lead sales, marketing, or revenue teams – this conversation will challenge how you think about enablement.Tune in and learn:+ How to fix forecast uncertainty+ How to build behaviour-led performance+ How to align revenue teams around real commercial oversightIf you care about predictable revenue, commercial common sense, and long-term alignment – this one’s essential.-----------------------------------------------------🔗 Links + CTAs-----------------------------------------------------🎓 Join our Demand Generation Program: https://theb2bplaybook.com/demand-generation-course🧠 Learn how to drive revenue across your organisation with CRO School: https://theb2bplaybook.com/cro-school💼 Need help running your own LinkedIn Thought Leadership Ads? https://theb2bplaybook.com/linkedin-ads-agency-----------------------------------------------------SUBSCRIBE to our channel: / @theb2bplaybook SUBSCRIBE to our newsletter: https://theb2bplaybook.com/newsletterGET the latest CONTENT: https://theb2bplaybook.com/-----------------------------------------------------00:00 Why Revenue Leaders Are Losing Confidence in Their Forecast04:40 FOMO vs FOBO: Why Buyers Are Frozen08:10 Is Your Pipeline Fake?11:20 Revenue Retention Is Changing Sales Behaviour14:00 Why Commercial Handover Is Broken16:20 The Smash-and-Grab Sales Problem19:50 The 2x2 Coaching Framework22:30 Toxic High Performers25:00 What Good Behaviour Looks Like29:30 Why Training Fails31:00 The Kirkpatrick Model33:10 Specialisation in Sales Teams36:10 Thinking Like a Franchise Owner39:40 You Are Your Calendar42:10 Growth Mindset in Revenue Teams48:20 SaaS vs Software With a Service54:30 Crossing the Chasm01:00:10 Revenue Enablement Society01:04:00 The Art and Science of Leadership-----------------------------------------------------👥 Are you a B2B marketer in a small team??💰 Need to bring in more revenue for your company (so sales and your boss love you??)Get the:🔹 strategy🔹 templates🔹 toolsSo you have everything you need to drive more revenue for your brand.See why other B2B marketers like you love The B2B IncubatorCheck out: https://theb2bplaybook.com/demand-generation-courseS08 E219 - The B2B Playbook#b2b #b2bmarketing #digitalmarketing #demandgeneration #salesleadership #salesadvice #revenueenablement