20+ senior operators.
One integrated firm.

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.

The founding team

Charlie Field, Founder and CEO of Win Win Advisors

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 and COO of Win Win Advisors

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

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.]

Senior operators. Every one.

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

Brad Feldman

Strategic Advisor

Mike Mascoll, Strategic Advisor

Mike Mascoll

Strategic Advisor

Van Murray, Strategic Advisor

Van Murray

Strategic Advisor

BO

Bill Oates

Strategic Advisor

ND

Natalie DeFord

Strategic Advisor

EW

Eric Wallert

Strategic Advisor

BN

Brian Norton

Strategic Advisor

DM

Dave McGeough

Strategic Advisor

BH

Brian Hilton

Strategic Advisor

SF

Shaquille Fontenot

Strategic Advisor

EF

Ed Field

Strategic Advisor

RT

Ron Trackey

Strategic Advisor

RC

Rick Cunningham

Strategic Advisor

MG

Matt Giarratani

Strategic Advisor

BW

Brian Worobey

Strategic Advisor

CH

Carleton Hall

Strategic Advisor

BR

Bern Risely

Strategic Advisor

JQ

Jose Quiros

Strategic Advisor

Work with the
best in the room.

Our advisors bring decades of operating experience — and a genuine interest in your success. Let's find the right fit for your challenge.

Book a Strategy Call info@winwinadvisors.com