Icebreaker

Warm up your reps before cold calls.

At Outsold, our sales coaching isn’t just theory—it’s built on decades of proven success. Our founder, Jamie May, brings the sharp, real-world strategies honed through My Business Sales Skills Coach—an intensive coaching approach built to unlock immediate results for business owners and sales teams alike.

But the roots go deeper. Jamie’s coaching ethos is shaped by the legacy of Noble May & Associates, a firm built by his father and known for its practical, results-driven business advisory work. This generational foundation means our coaching is not just about confidence or charisma—it’s about commercial outcomes, clear frameworks, and building scalable sales systems that last.

Whether you’re a founder doing sales yourself or leading a growing team, Outsold offers the structured coaching and pitch sharpening to take your sales game from good to unstoppable.

Phase 1: Discovery & Design

(Week 1-2)

Audit sales process, existing pitch material, personas

  1. Interview 1–2 top reps + manager

  2. Identify 2–3 key sales conversations (cold pitch, value prop, objection handling)

Phase 2: AI Training Sprint

(Week 3)

You record/extract versions of:

  • Cold opens / value prop articulation

  • Feature → Benefit mapping

  • Objection-handling

  1. Upload this into Icebreaker

  2. Customise AI to simulate ideal buyer personas

  3. Optional: use voice cloning, if desired

Phase 3: Team Coaching & Tool Integration

(Week 4-5)

Live workshop or remote onboarding of reps

  1. Real-time roleplay with Icebreaker + review of pitch quality

  2. Add Icebreaker into weekly practice rhythm

  3. Feedback loop: improve model with staff interactions

Phase 4: Ongoing Enablement

(Optional Monthly)

Monthly sales coaching, pitch reviews, AI model refinement

  1. Sales manager enablement (analytics, best practice reinforcement)