Jamie May

Commander
DISC Type : D

Co-Founder at Icebreaker

Greater Sydney Area, Australia

Overview

Jamie is the Managing Director of Outsold, where he builds scalable, full-cycle sales systems for B2B businesses. With a background in Commerce from Western Sydney University, he specializes in creating revenue infrastructure for founders who dislike selling. Colleagues and clients describe him as exceptional, knowledgeable, and approachable.

Outside of his direct sales work, Jamie shows an interest in broader business strategies and cutting-edge science. He follows developments from institutions like the Harvard Business Review and the NASA Glenn Research Center, suggesting a curiosity for both high-level management theory and technological innovation.

Despite being a top sales professional, he has stated, “I have never loved sales. Not once. In fact, I have mostly hated it. ”

Personality Overview

Strong-Willed

Decisive

Very Quick

They like to be in a position where they can control the conversation and terms.  They like to act fast and expect others to do the same. They are not focused on building rapport and relationships.

Topics They Care About

Founder Sales Aversion
His professional focus is on building sales systems for founders who hate selling, addressing their key pain points and taking sales functions off their plate.
Sales as a Service
He founded Outsold as Australia’s first true “sales-as-a-service” agency, offering a full-cycle, outsourced solution from prospecting to closing deals for clients.
Sales Process Design
He has a history of redesigning sales processes to dramatically increase conversion rates, implementing new CRM systems, playbooks, and messaging for clients.

Media Appearances

Jamie has no verified media appearances

Work History

4-2025
Co-Founder at Icebreaker
7-2019
Managing Director/ Fractional Sales Architect at Outsold
6-2019 - 9-2020
State Manager NSW at Asta
2-2018 - 5-2019
APAC Head of Sales at CS Technology Australia now part of Accenture
3-2015 - 1-2017
Closer & sales lead at Avante IT

Education

1999 - 2001
bachelor of commerce from Western Sydney University
Business Management from TAFE NSW

More Information

Social Presence :

Prographics :

Exp : 29 Location : Greater Sydney Area, Australia Job Level : Senior Designation : Co-Founder at Icebreaker
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Insights For Selling To Jamie

During A Call Or A Meeting

DO's

  • Speak about competitive differentiation that your product offers
  • Hold your ground without indulging in one-upmanship
  • Make sure that you circle back fast on any action items, it wins their trust

DONT's

  • Do not back off when challenged, respond with a confident, objective answer instead
  • Don't try too hard to forge relationships with them
  • Avoid being too verbose

When Cold Calling

When Writing An Email

While Negotiating & Closing

    The secret to closing fast with Jamie is

  • Confidence in impact is paramount to them, followed by a sense of achievement and ROI.
  • Will you ever get a clear answer from Jamie

  • If they decide not to go ahead, they will say no without hesitation.

Insights For Deal Planning

    How fast (or slow) will Jamie move?

  • They can take decisions very fast if you manage to convince them.
  • Can Jamie take some risk or not?

  • The risks don’t matter much to them.

You And Jamie

Personality Compatibility


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