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The Mid-Market Squeeze
Chris Stegh · 2026-06-16 · via Forbes - Innovation

Christian Stegh, CTO and VP of Strategy at eGroup Enabling Technologies.

getty

​In the 1990s and 2000s, midsized retailers were in a tight spot. Montgomery Ward and Sears, shadows of their former selves, were done in once and for all. Soon, too, were Carson’s and Bergner’s. They were simultaneously pinched by larger chains like Target and Walmart with nationwide coverage and clout, and by specialty firms like Best Buy and Dick’s, which focused on a narrower audience. And beyond the brick-and-mortar, Amazon was forcing those left standing to compete on margins, service or quality.

AI is making the squeeze a real possibility for broader segments of midsized businesses. And while large enterprises and single-employee startups are making headlines, many midsize firms have yet to invest in GenAI. This puts them in a squeeze.

Why This Time Is Already Different

Traditionally, midsized businesses had advantages: less red tape, focused funding and rapid time to market.

These traits often made them formidable competitors. AI is making a more recognizable impact in large enterprises. Banks, large retailers and software firms dominate AI’s headlines.

Walmart’s CEO credits technology and AI for “helping us create great customer solutions, reduce friction, simplify decision-making and pinpoint where our inventory is.” Mid-markets are more likely to make decisions from spreadsheets.

Big banks are betting big on their AI future. Bank of America has 90 AI apps running and all 200,000 employees can use AI. They’ve spent hundreds of millions seeking cost savings and customer service. “We are committed to embedding AI into how we work,” Citigroup CEO Jane Fraser said.

Pressure From Above Is Mounting

Why are larger enterprises poised to squeeze their smaller contemporaries?

1. They’re investing. Enterprises have been able to fund more R&D to experiment, train their own models, build more pilots and license more Copilots. KPMG’s Global CEO Outlook last fall showed that 69% of CEOs intended to spend 10% to 20% of overall budget on AI. However, in a similar study of midsized CFOs, 57% of companies intended to allocate 1% to 5%, while another 28% had zero or nearly zero allocated.

2. Substantial IT teams are eagerly experimenting. Agentic AI’s gains are most prevalent in software development, a strength of larger organizations. On the other hand, more midsized businesses strictly use SaaS and don’t develop their own apps. They haven’t experienced the amazing outcomes of Claude Code or GitHub Copilot that justify investments in adjacent processes.

3. Their data and systems are more modernized. Data is the fuel of AI, and with easier access, organizations can realize value quickly. It’s more difficult for AI to reason over data in disparate, distinct locations, and mid-markets are more likely to still have a file server squirreled away.

The Threat From Below

Large eating the small isn't the only scenario. Pressure from below is still evident in retail. Look no further than the online mattress companies dismantling the mattress store chains. Even specialization won’t save them. In the Web 2.0 era, startups like NetFlix disrupted Blockbuster on their way to dominance.

In the AI era, cloud-first, tech savvy upstarts will first begin to cross the moats of their midsized competitors. So too will some agentic AI-based one-person companies, whose automations and specializations could catch midsized organizations flat-footed. Look no further than the numerous reports about the SaaS-Pocalypse due to purpose-built, vibe-coded agentic AI apps.

Where Mid-Market Still Has The Advantage

Providing a more nimble, personalized experience are givens. A few specific flanking maneuvers can also help midsized orgs thrive in the age of AI.

Modernize faster. Data is the fuel of AI. Making it ready for AI involves moving it to cloud storage systems like SharePoint and data lakes. The fewer systems an organization has, the quicker AI can start reasoning over their data. Advantage: midsized organizations.

Expedite decisions. Less bureaucracy, the easier the decisions about which data to make AI-ready.

Reorganize wisely. Mid-markets can supercharge change by integrating AI-savvy businesspeople and tech teams. At Verdantas, two AI champions from the line of business were brought into the IT transformation team to expedite adoption and develop impactful solutions.

Reengineer processes. AI can’t solve complex problems without processes that are redesigned for AI. “It has become increasingly clear that our operating processes need to reflect the gains that will come from these transformational technologies,” Goldman Sachs CEO David Solomon said. Simpler systems are better suited for an AI operating model.

Next Steps For Leaders

Retailers in the ’90s had several years to see the squeeze coming. The same evidence is brewing in the 2020s. Yet despite the big-company headlines, midsized firms aren’t far behind. “It is a long, expensive and risk-constrained transformation,” Wells Fargo analyst Mike Mayo wrote in a note to investors.

It’s not too late for midsized organizations to catch up, if leaders stop:

• Running disconnected pilots

• Expecting AI to fix disparate data and suboptimal processes

• Waiting for perfection before getting started

Instead, leaders who get ahead will start to:

• Focus on a single workflow

• Intentionally invest in optimized data, tools and training

• Measure success (while expecting some struggles as this journey gets started)

And simultaneously start to:

• Empower business champions

• Redesign other processes for AI

• Modernize tech to be AI-ready

Then, mid-markets can get the real unlock: making AI a part of an updated operating model, not just a novel technology.

With more speed and less friction, mid-markets can not only avoid the squeeze, but can outperform their more well-funded rivals and stay ahead of the native-AI firms nipping at their heels. The ones that win will be the ones who use AI to rebuild how work gets done.​


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