The Best of the Brutal Truth about B2B Sales & Selling - The show focuses on the enterprise Sales Process WHAT IS WORKING TODAY IN LARGE ENTERPRISE SALES
14 snips
Feb 16, 2026 
Jay (JD) Douglas, a 27-year enterprise sales veteran in HR/HCM, shares hard-won wisdom. He talks about building trust with candor, navigating politics in large organizations, mapping complex deals visually, using curiosity to diagnose priorities, working with procurement as an ally, and embracing deliberate practice and failure to win big, complicated deals.
AI Snips
Chapters
Transcript
Episode notes
Checklists Aren't A Process
- Checklists list artifacts but don't show context or next moves in a complex sale.
- Assigning tasks to the customer can backfire because they own the problem, not your sale.
Identify Complex Deals Early
- When a deal involves more than three influencers or multiple departments, treat it as a complex sale.
- Use advanced processes and coaching to close deals $50K+ where doing nothing is the default.
Set Expectations And Be Candid
- Set expectations and be candid about how you operate at the start of a relationship.
- Say what you'll do, invite them to call you out, and show up consistently to build trust.