B2B sales for founders: how to run real discovery, align a proof of value, and close without racing to discounts. Outcome: shorter cycles, cleaner handoffs, and deals that stick.

In this episode of the Burn The Playbook Podcast, host Marc Crosby (Digital Rebels Consulting) digs into the WINGS Sales Program with Raz Vicerabin. Raz led revenue teams through IPO at Riskified and now teaches founders the sales fundamentals. We cover mindset shifts, first hires, metrics that matter, and a dead-simple POV alignment that stops deals from dying after the demo. Raz is bringing WINGS to NYC on February 3–4, 2026. (LinkedIn)

What you’ll learn

• Why discovery beats pitching and how to stay in investigator mode
• A 15-minute prep routine that saves wasted meetings
• The POV Alignment: success criteria, effort, economics, green light
• Negotiation basics founders miss and how to anchor high with a pricing ladder
• When to hire your first AE or VP Sales and what must be true
• The two pipeline “cemeteries” and how to build momentum after a demo
• Metrics that matter: stage-to-stage conversion over “big pipeline” vanity

Chapters
00:00 Intro + who is Raz
00:38 Recording at Riverside
01:48 Raz’s path: law, IDF interrogator, first AE
03:21 Builder-to-investigator mindset shift
04:53 The #1 mistake on first calls
06:28 How to prep for discovery
09:22 Teaching sales at universities vs founders
11:34 The WINGS program format
12:14 1:1 consulting vs workshops
13:32 Negotiation influences and ZOPA
15:36 Handling aggressive buyers
17:00 Discount pressure and value gaps
18:25 When to walk from a deal
19:43 Timing the first sales hire
21:05 Bad metrics vs stage conversion
22:25 Why deals get “stuck”
23:13 The POV Alignment framework
27:55 Curiosity as the top trait
29:24 Burn It or Build It: 10 hot takes
41:14 Where to find Raz + NYC dates

Who this helps

• Early-stage founders in B2B or cyber selling into the enterprise
• Technical leaders new to sales who need a practical operating cadence
• Sales leads cleaning up post-demo drift and endless POVs

Guest

• Raz Vicerabin — Founder, WINGS Sales Program for Founders; B2B Sales Lecturer
• Website: https://www.sales-wings.com (Home)
• LinkedIn: https://il.linkedin.com/in/raz-vicerabin (LinkedIn)

Host

• Digital Rebels Consulting — https://DigitalRebelsConsulting.com
• Host: Marc Crosby, Burn The Playbook Podcast

• Website → DigitalRebelsConsulting.com
• Linktree → https://linktr.ee/digitalrebelsconsulting
• Socials → Follow us on LinkedIn www.linkedin.com/in/marcccrosby
• Email → marc@digitalrebelsconsulting.com
• Apple Podcasts → https://podcasts.apple.com/us/podcast/burn-the-playbook/id1828969451
• Burn The Playbook Website → https://www.buzzsprout.com/2522863

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