Talent · Technology · Training
Win Win Advisors helps mid-market businesses hire the right talent, build the right tech stack, and train their teams to lead. We're not a staffing agency or an IT vendor. We're a senior advisory network that works across all three.
Contract, temp, and permanent staffing plus retained search across IT, sales, and leadership. We place the people who move the needle.
Cloud, managed security, unified communications, and fractional C-suite. The right stack for where you are — and where you're going.
Sales onboarding, leadership development, and IT/cybersecurity training — built for your organization, not off the shelf.
Why Win Win
A network, not a headcount
20+ senior operators who've held the roles they advise on. Not generalists — former CIOs, CISOs, F500 L&D leaders, M&A operators, and sales executives who return to the work because they choose to.
Talent and technology 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.
Training that sticks
We don't deliver workshops and disappear. Our training programs are built around your specific org, culture, and gaps — then reinforced over time. Skills transfer, not slide decks.
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
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Trusted By
Client logos coming — request from Win Win team
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 Advisory Bench
Our team includes former CIOs, CISOs, F500 L&D leaders, M&A operators, and sales executives — not generalists. People who've done the job at the highest level and return to it because they want to.
Charlie Field
Founder & CEO
Allison Field
Co-Founder & COO
Michael Ahearn
VP Business Development
Brad Feldman
Strategic Advisor
Mike Mascoll
Strategic Advisor
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.