There is a discovery that mid-market business owners tend to make at the worst possible moment. A buyer or investor arrives, digs through the operations and the financials, and surfaces problems the owner knew about in some vague sense but never had reason to measure precisely. By the time those gaps appear in a formal process, the seller is managing them under deal pressure rather than addressing them on their own terms.
Michael Cupps launched Enterprise Diagnostics in late 2025 to bring that reckoning forward. The Dallas-area company provides AI-powered business diagnostics for mid-market companies and PE-backed portfolio companies, built around a premise Cupps states plainly in the company’s founding materials: most businesses deploy AI before they know where value is actually leaking.
The argument against that sequence is not original. What Enterprise Diagnostics offers is a structure for acting on it. The company’s core services run across three diagnostic tracks. Baseline examines financial health, benchmarking margins against sector peers and identifying cost structure problems to validate the earnings quality that buyers will scrutinize in diligence. Alpha Vector addresses the customer side, looking at retention rates, customer concentration, and cohort performance to test whether a company’s revenue is genuinely defensible. Alpha Frontier covers AI readiness, identifying where manual processes drag on margins and where automation could close the gap.
For owners who want to see where they stand before committing to a full engagement, the company offers a free CRED Score assessment. Sixteen questions return an immediate readiness score across four categories that map directly to buyer scrutiny: Customer Health, Revenue Quality, Earnings Certainty, and Market Demand. Each score comes with suggested action steps. A fourth paid service, FastStart, is for companies that have already identified what they want to automate and want to move directly to building and deploying an AI agent. Per the company, all paid engagements are fixed-fee with scope defined before work begins.
Cupps arrived at this from a career spent on the other side of the same conversation. Over more than 25 years in the enterprise software sector, by his professional account, he held senior roles in sales, marketing, operations, and channel development. At ActiveOps, a workforce and operations management software company, he served as Executive Vice President for North America growth, working on market expansion and what he describes as go-to-market partnerships with technology companies including Microsoft, UiPath, Blue Prism, and IBM. Earlier positions included senior roles at Rulesware, a digital transformation consultancy, and before that at Global 360, Zimbra, and webMethods Software AG.
That career put Cupps in the room repeatedly where enterprise software was being proposed as the answer to operational inefficiency. Enterprise Diagnostics is built on the prior question: which inefficiencies are worth addressing, and in what order.
Alongside the corporate work, Cupps has written about prioritization at the individual level. His book “Time Bandit,” published by Rethink Press and available on Amazon, addresses priority management and habit formation as practical professional tools. A companion Priority Matrix, released as a free digital tool earlier this year, puts the book’s framework into a working workspace for executives and project teams dealing with a common bottleneck: more ideas in motion than capacity to act on them. He contributed articles on business leadership and productivity to the Fast Company Executive Board and was previously a Forbes Communications Council member. He also hosted a podcast called The Habit Architect, part of an earlier coaching practice called Coterie Solutions.
Enterprise Diagnostics is still in its early stages. The company’s About page notes it was co-founded by two people who grew up on farms and ranches, one in Oklahoma and one in Texas, which the company cites as context for how it approaches problems that don’t have clean answers. The operating model relies on what the company calls Forward Deployed Engineers: people who embed directly with customer teams on-site to build and deploy solutions rather than deliver recommendations at a distance. The company is currently seeking strategic investors through a crowdfunding campaign on WeFunder.
The organizing logic across all of it is the same: establish what the problem actually is before deploying anything. How much that sequencing matters in practice depends on where a given business is standing. The companies Enterprise Diagnostics is after are the ones expecting to find out, one way or another, within the next few years.
