Enterprise Diagnostics Launches Wingman: An AI Tool Built for the Silver Tsunami of Business Leaders

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Voice-first competitive intelligence serves the 50+ executives running America’s mid-market, distributed through the coaches and consultants they already trust

DALLAS, TX, UNITED STATES, May 20, 2026 /EINPresswire.com/ -- Enterprise Diagnostics today launched Wingman, an AI competitive intelligence platform built for the experienced business leaders most AI tools have ignored: the Gen X and Baby Boomer executives running 2.3 million Baby Boomer-owned U.S. small businesses. This is the “silver tsunami” generation, now being told they need to learn prompt engineering to stay relevant.

Wingman takes a different approach. After a setup that takes minutes, users name up to seven competitors. Wingman scans each across four categories and ten topics, including pricing moves, hiring patterns, product launches, and market positioning, and surfaces what matters on a red, yellow, and green dashboard. Users don’t write prompts. They choose how they want to engage with the AI based on their confidence in the moment:

“I’ll lead, let’s talk”: for leaders who want a thinking partner
“Let’s brainstorm this together”: for leaders who want to explore options
“Tell me what to do”: for leaders who want a clear recommendation

Designed for Voice or Prompts
Every Wingman conversation can be conducted entirely by voice. For experienced leaders who didn’t grow up writing prompts, the typing interface itself is often the barrier to AI adoption. Voice removes that barrier. A leader can talk through a competitor’s pricing move between meetings the same way they’d talk it through with a trusted advisor. No typing, no syntax, no “prompt engineering” vocabulary required.

“Most AI products treat new users like they’re embarrassed to ask basic questions,” said Michael Cupps, Founder of Enterprise Diagnostics. “We built Wingman for the opposite person: the leader with thirty years of pattern recognition who doesn’t need AI to think for them. They need AI to keep them current, give them a starting point, and get out of the way.”

Distributed Through Coaches
Wingman’s primary go-to-market is distributed by executive coaches and consultants, who purchase accounts in bulk and provide them free to clients and prospects, turning a strategic tool into a relationship-building asset. Ten coaches are participating in the launch pilot, with 34 business owners currently using Wingman in beta.

“My clients are running real companies with real P&L’s, and they’re tired of being told they’re behind on AI. They don’t want a class. They want a tool that respects their experience and gives them something useful in five minutes. Wingman is the first thing I’ve seen that actually does that,” said Adam Ritchie, Founder of High Potential Group.

“Coaches don’t need another piece of software to sell. They need a way to stay valuable to clients between sessions. Wingman is designed as a gift the coach gives the client. The coach pays once, the client uses it free, and the relationship deepens. That’s the whole point,” said Brandon Lee, Founder of Brandon Lee LLC, who is leading distribution for Wingman.

Why Now: The Silver Tsunami Meets the AI Divide
According to Project Equity, 2.3 million U.S. small businesses are owned by Baby Boomers approaching retirement, a generational shift representing roughly one in six American jobs. Nearly half of U.S. small-business owners are 55 or older. These leaders are being asked to adopt AI at the same moment they are being asked to think about succession, valuation, and exit. Wingman exists to make AI a strength these leaders can bring to those decisions, not another thing on a list of skills they are supposed to learn first.

Availability
Wingman is available now through participating coaches and consultants. A direct subscription is also available for solo professionals, designed for the coach who wants to use the tool personally, or for the business owner who has seen Wingman through a colleague and wants their own account. The coach-distributed model remains the company’s primary focus. Learn more at enterprisediagnostics.ai
About Enterprise Diagnostics
Enterprise Diagnostics builds practical AI agents for small and mid-market companies, with a focus on serving leaders who want results without the learning curve. The company partners directly with business owners to identify high-friction tasks and deploys working solutions within a week. Wingman is the company’s first general available - packaged product.

Michael Cupps
Enterprise Diagnostics, Inc
+1 972-523-6690
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