The B2B Playbook #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 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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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