Technology  ·  Fractional  ·  Infrastructure

When the right people
meet the right technology —
everyone wins.

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.

Technology

Cloud, managed security, unified communications, and fractional C-suite. The right stack for where you are — and where you’re going.

Fractional

fCRO, fCISO, fCIO, and fCTO expertise at the right engagement level. Senior strategy without the full-time cost — until you’re ready for it.

Infrastructure

Buy, sell, lease, migrate, renovate, and operate Data Centers across North America and Europe. Board-level data center strategy for the AI era.

A network,
not a headcount.

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.

20+
senior strategic advisors
3
integrated disciplines
1
integrated advisory firm

What our clients and partners say

“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.

20+
senior strategic advisors
3
integrated disciplines
1
integrated advisory firm

Executive-level strategy
without the full-time
commitment.

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.

fCRO
fCISO
fCIO
fCTO
Learn About Fractional Leadership
Charlie Field, Founder and CEO of Win Win Advisors

Charlie Field — Founder & CEO

Led by operators.

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 and CEO

Charlie Field

Founder & CEO

John Vittori, Co-Founder

John Vittori

Co-Founder

Bill Oates, Co-Founder

Bill Oates

Co-Founder

Meet the Full Team →

Ready to find
your win?

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.

Book a Strategy Call [email protected]