Closing Enterprise Deals Without Losing Your Calendar or Soul | Ben Sheppard

I felt like I was watching an action packed short movie with serious suspense… With Ben Sheppard (strategic advisor, coach, and fractional operator), we explore life, leadership, and business from the inside out, and what it takes to close meaningful enterprise deals without losing yourself, your calendar, or your conviction.

Ben has well and truly lived the founder journey from seed to Series D and brings a rare mix of fearlessness, structure and humanity. We talked about creating environments where teams think clearly, move with intention, and stop confusing constant motion with progress. One of my favourite ideas was his leadership communication rhythm: early week is for identifying the real problem, midweek is for building clean solutions. Simple, and powerful.

Through the Bee Formless™ methodology, we explored:

LEARN (Letting go)
✨ Perspective under pressure: how unfamiliar environments and early challenges reveal what matters most.
✨ Founder reality: staying calm inside chaos when everything feels urgent and undefined.

UNLEARN (Reimagine and reshape)
✨ Enterprise deals without theatre: how clarity and precision outperform panic and last-minute scrambling.
✨ Courage as a sales skill: building confidence through reps, not perfection.

RELEARN (Test and implement)
✨ Founder support that actually helps: fractional coaching that strengthens decisions, not dependence.
✨ AI and LLMs: what founders must understand to use them wisely without losing judgment in 2026.

ACTIVE RECOVERY (Reflect and reset)
✨ Founder stamina: sustaining energy through change without disappearing into the business.
✨ Reality check rhythms: practices that keep perspective when the work becomes all-consuming.

About Ben Sheppard
Ben Sheppard is a strategic advisor, coach, and fractional operator who helps founders close enterprise customers and raise capital. He has advised organizations including Bloomberg Philanthropies and the Rockefeller Foundation, writes the Founder Insights newsletter, and works hands-on with startups via bensheppard.xyz.

Where to find more from Ben
🌐 Website: https://bensheppard.xyz/
🔗 LinkedIn:   / txshep  
📰 Newsletter: https://sheppardb.substack.com/about

Where could you tighten your week so you spend less time reacting and more time solving the real problem?

If you’re navigating transition or friction and you’re ready to reshape your life, leadership, or business from the inside out, book a complimentary 60-minute Bee Formless™ Diagnostic.
This is a deep clarity session and often the first step into the Bee Formless™ methodology.
Book here: https://calendly.com/beeformless/prog...

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