The Win Win Advisory Bench
People who've led at the highest levels — and stay engaged because they want to, not because they have to. Our advisors have held the roles they advise on.
Leadership
Charlie Field
Founder & CEO
[PLACEHOLDER: Charlie Field bio — request from Win Win team. Recommend pulling from winwinadvisors.com and cleaning up for tone. Suggested framing: career background, founding story of Win Win, specific industries or companies worked with, areas of expertise across talent/technology/fractional leadership.]
Allison Field
Co-Founder & COO
[PLACEHOLDER: Allison Field bio — request from Win Win team. Recommended framing: operations background, role in building Win Win's delivery infrastructure, specific areas of ownership (training programs, client relationships, team coordination).]
Michael Ahearn
VP Business Development
[PLACEHOLDER: Michael Ahearn bio — request from Win Win team. Recommended framing: business development background, markets served, how he connects client needs to Win Win's advisory network.]
The Advisory Network
Win Win's advisor network brings decades of operating experience across IT leadership, sales, L&D, M&A, and cybersecurity. These are practitioners — not consultants who've never held the role.
Brad Feldman
Strategic Advisor
Mike Mascoll
Strategic Advisor
Van Murray
Strategic Advisor
Bill Oates
Strategic Advisor
Natalie DeFord
Strategic Advisor
Eric Wallert
Strategic Advisor
Brian Norton
Strategic Advisor
Dave McGeough
Strategic Advisor
Brian Hilton
Strategic Advisor
Shaquille Fontenot
Strategic Advisor
Ed Field
Strategic Advisor
Ron Trackey
Strategic Advisor
Rick Cunningham
Strategic Advisor
Matt Giarratani
Strategic Advisor
Brian Worobey
Strategic Advisor
Carleton Hall
Strategic Advisor
Bern Risely
Strategic Advisor
Jose Quiros
Strategic Advisor
Our advisors bring decades of operating experience — and a genuine interest in your success. Let's find the right fit for your challenge.