Technology · Fractional · Infrastructure
Win Win Advisors helps mid-market businesses build modern technology infrastructure, access fractional executive leadership, and navigate data center strategy. A senior advisory network — not a vendor.
Cloud, managed security, unified communications, and fractional C-suite. The right stack for where you are — and where you’re going.
fCRO, fCISO, fCIO, and fCTO expertise at the right engagement level. Senior strategy without the full-time cost — until you’re ready for it.
Buy, sell, lease, migrate, renovate, and operate Data Centers across North America and Europe. Board-level data center strategy for the AI era.
Why Win Win
Senior operators, not generalists
20+ advisors who’ve held the roles they advise on. Former CIOs, CISOs, F500 L&D leaders, M&A operators, and sales executives who return to the work because they choose to.
Technology and people aren’t separate problems
Most firms force you to choose a lane. Win Win sits at the intersection — because the best technology deployments fail without the right people, and the best hires fail without the right systems.
Data center strategy for the AI era
As AI infrastructure demands accelerate, data center decisions have become board-level priorities. Our advisors have navigated location, capacity, power, connectivity, and compliance for companies across North America and Europe.
Fractional leadership when you need it
Access fCRO, fCISO, fCIO, and fCTO expertise at the right engagement level for where you are. Senior strategy without the full-time cost — until you’re ready for it.
Built on Experience
“Charlie is one of two people that I would do business on a handshake and still rest easy. I have had the pleasure of working with Charlie since 2000 on various projects and he has always been more than fair in business dealings, worked hard as our customer advocate and been extremely responsive when an emergency arose. All round, a great individual to do business with.”
— Ted Hopcroft, Vice President of IT, Technology, and Professional Services, Americas at Marriott International
“I have had the pleasure of working with Charlie Field as a colleague and as a business partner. Charlie Field was my go to guy in hospitality regarding anything to do with business communications and bandwidth. I have never witnessed in my career such amazing passion for not only the client, but for one’s fellow employees. Starwood Hotels was a big shared client of Charlie’s company and mine as well, and all of the Executives at Starwood knew that if you wanted something accomplished at PAETEC, you need only look to Charlie to get it completed, and successfully. There is a level of enthusiasm and caring that cannot be taught in this business, but is inherit in one’s nature, and Charlie Field exhibits it in everything he does.”
— Trey Turbeville, Director, Sales & Marketing, Repeated Signal Solutions, Inc.
Fractional Leadership
When your company needs a CRO, CISO, CIO, or CTO but isn’t ready for a full-time hire, Win Win’s fractional leadership model gives you senior-level strategy and execution at the right engagement level for where you are.
Charlie Field — Founder & CEO
The Founding Team
Win Win was built by people who’ve led in the field — not generalists. Our founders bring decades of experience in hospitality technology, data center strategy, and enterprise advisory.
Charlie Field
Founder & CEO
John Vittori
Co-Founder
Bill Oates
Co-Founder
Trusted Partners
No pitch deck. No hard sell. A conversation about where you’re headed and whether we’re the right team to help you get there.