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
Founder & CEO | Business Development | Strategy | Leadership | Start-Ups
John Vittori
Co-Founder
Global Network Infrastructure | Channel Development | Business Development | Energy
Bill Oates
Co-Founder
Hospitality Industry Technology Hall of Fame | CIO - City of Boston | CIO - Commonwealth of Mass | Public Sector CIO Innovator of the Year | Boston College Faculty
The Advisory Network
Win Win’s advisor network brings decades of operating experience across IT leadership, sales, M&A, cybersecurity, and hospitality technology. These are practitioners — not consultants who’ve never held the role.
Matt Giarratani
Strategic Advisor | CISO | Infrastructure Applications | Financial
Carleton Hall
Cloud | Infrastructure | AI | IaaS
Van Murray
Strategic Advisor | Fractional CIO | Executive Leadership | Digital Transformation | M&A
Brad Feldman
Strategic Advisor | Strategic Business Development | Service Provider | Product Marketing
Allison Field
Recruiting | L&D | Strategy | Executive Coaching
Mike Mascoll
Strategic Advisor | Enterprise | Mobility | DEI | Marketing | Leadership
Michael Ahearn
VP of Business Development | Contact Center Enterprise | PBX Systems | Product Development
Eric Wallert
Strategic Advisor | Nationwide L&D Leadership for an F500 Communications Service
Brian Norton
Strategic Advisor | Technology Distribution | Channel | Executive Leadership
Dave McGeough
Strategic Advisor | Nationwide L&D Leadership for an F1000 Communications Service Provider
Brian Hilton
Technology Program Management | Cybersecurity Managed Services
Shaquille Fontenot
Strategic Advisor | Marketing | Content Creation
Ed Field
Strategic Advisor | M&A | Operations Manufacturing | Strategy
Ron Trackey
Strategic Advisor | Product Engineering | Innovation | Software | Security
Rick Cunningham
Strategic Advisor | Vertical Market Strategy | Energy | Executive Leadership
Bern Risely
Strategic Advisor | Customer Success
Shawn Donahue
Healthcare IT Leadership | Program Management | Vendor Management
Chris Golden
fCISO | CMMC | FedGov | Military | Healthcare
Our advisors bring decades of operating experience — and a genuine interest in your success. Let’s find the right fit for your challenge.