The B2B Playbook podcast

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

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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 calendar


If 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 oversight


If you care about predictable revenue, commercial common sense, and long-term alignment – this one’s essential.


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🔗 Links + CTAs

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00:00 Why Revenue Leaders Are Losing Confidence in Their Forecast

04:40 FOMO vs FOBO: Why Buyers Are Frozen

08:10 Is Your Pipeline Fake?

11:20 Revenue Retention Is Changing Sales Behaviour

14:00 Why Commercial Handover Is Broken

16:20 The Smash-and-Grab Sales Problem

19:50 The 2x2 Coaching Framework

22:30 Toxic High Performers

25:00 What Good Behaviour Looks Like

29:30 Why Training Fails

31:00 The Kirkpatrick Model

33:10 Specialisation in Sales Teams

36:10 Thinking Like a Franchise Owner

39:40 You Are Your Calendar

42:10 Growth Mindset in Revenue Teams

48:20 SaaS vs Software With a Service

54:30 Crossing the Chasm

01:00:10 Revenue Enablement Society

01:04:00 The Art and Science of Leadership


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S08 E219 - The B2B Playbook

#b2b #b2bmarketing #digitalmarketing #demandgeneration #salesleadership #salesadvice #revenueenablement

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