Jamie May in

Jamie May

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Co-Founder at Icebreaker
📍 Greater Sydney Area, Australia

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. ”

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Experience
29 Years
Current Role
Co-Founder
Job Level
Senior
Location
Greater Sydney Area, Australia
Personality Overview

How Jamie shows up

Communication Style
Decision Approach
Work Preference

Behavioral traits and communication patterns that shape how this person evaluates opportunities, builds trust, and makes decisions in professional settings.

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Priorities

Topics Jamie cares 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.
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Career

Work history

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

Media appearances

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Education
1999 - 2001
bachelor of commerce
Western Sydney University
Business Management
TAFE NSW
Social presence
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Behavioral profile

DISC profile (public)

DISC behavioral profile

Dominance, influence, steadiness, and calculativeness scores with guidance on how this person prefers to communicate and decide.

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