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Mark Cuban sees another massive workplace shift coming, and it could impact how Americans build careers.
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The billionaire investor of ‘Shark Tank’ fame believes AI could now play a much bigger role in how workers deal with challenging situations, sharpen their judgment, and prepare for more valuable work.
In turn, that allows businesses to train people a lot quicker and at a far lower cost.
Cuban is among the select group of investing giants who remain broadly optimistic about AI. He feels that businesses that embrace AI will become much more productive, while workers who use it will still find opportunities.
Nevertheless, that prediction underscores an uncomfortable trade-off.
AI opens the door to supposedly better training, but it replaces human mentorship and the early career work that paved the way for people to move up the ranks.
Mark Cuban’s AI job simulator vision is already taking shape
According to Business Insider, citing a July 24 X post from Mark Cuban, the billionaire investor believes the next major AI application will be an open-weight or open-source job simulator.
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Cuban believes that workers will have fewer colleagues, supervisors, and routine workplace interactions from which they can absorb experience. In response, businesses could ask company veterans and other domain experts to encode their knowledge into realistic scenarios, revamping onboarding as we know it.
Think of scenarios like a junior lawyer rehearsing a deposition, a doctor responding to an AI patient, or an electrician diagnosing a simulated fault.
Like pilots and racing drivers, employees will be able to continue to practice difficult or dangerous situations without exposing themselves to the financial, reputational, or safety consequences of making mistakes in their real lives.
Some corporations are already applying this innovative approach.
Bank of America said that employees wrapped up over 1 million AI-powered conversation simulations in 2024. The bank recreates client interactions, allowing workers to rehearse responses and receive immediate feedback before speaking with actual customers.
Amazon’s AWS offers a Meeting Simulator in which employees speak or type to AI characters that represent executives, technical experts, and other stakeholders. Users can also practice and explain products, address objections, and gather requirements, then receive instant feedback on their communication.
Skillsoft’s CAISY similarly allows employees to rehearse difficult business, leadership, and compliance conversations in a controlled environment. At the same time, Docebo allows companies to build customized role-playing exercises delivered via voice or text, with AI providing performance feedback after every exchange.
Private capital is also following that same trend.
Yoodli, an AI role-playing and communication-coaching platform, raised $40 million in Series B funding in December 2025, bringing its disclosed funding to nearly $60 million. Its software recreates sales calls, interviews, leadership conversations, and customer objections, then scores users and suggests areas for improvement.
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What is Mark Cuban’s broader view on AI and jobs?
Cuban argues AI adoption for employee training is unavoidable.
Companies that use AI effectively will continue outperforming those that don’t, and it’s unwise for employers and colleges to wait for those skills to be defined.
However, at the same time, Cuban, unlike for example Tesla CEO Elon Musk, doesn’t see AI as a complete substitute for people. He argues that AI models still struggle with real-time context, consequences, and social judgment, among other things.
The shifts may hit entry-level hiring at large businesses, but Cuban sees opportunities for small businesses needing younger workers who can apply AI to their jobs. On top of that, he is also more bullish on practical AI applications instead of data center spending, warning that efficiency gains could leave some infrastructure underused.
AI simulators may deepen the problem they claim to solve
I feel as though AI simulators might actually weaken the traditional career ladder by removing another step.
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For instance, Stanford researchers found a 16% drop in employment among workers aged 22 to 25 in the most AI-exposed occupations, even after accounting for company-level shocks.
However, a May 2026 Strada survey of 1,500 executives complicates the pessimistic view.
More than three times as many executives expected AI to increase entry-level hiring as reduce it. However, 41% said AI had already reduced the number of skill-building tasks, while 42% reported giving junior workers more judgment-based responsibilities.
So in essence, businesses might still hire graduates, but expect them to exercise senior-level judgment while taking away the bulk of the work that helped develop that judgment.
That notion is also supported by PwC, which similarly found that AI-exposed entry-level vacancies were seven times more likely to demand traditionally senior skills, including leadership and judgment.
Cuban’s simulators might help narrow that gap, but they may also institutionalize it. Senior employees might encode their experience into proprietary systems, allowing businesses to scale up training with a lot less direct mentorship.
The second big risk is that employers might first look to automate apprenticeship and then sell simulation as its replacement.
Companies would then gain ownership of institutional knowledge, control over what counts as “good judgment,” and potentially another system for measuring employees’ performance.
How junior roles shaped some of America’s biggest CEOs
Entry-level work has actually served a far bigger purpose than just cheap labor. For many future CEOs, it helped build the judgment, empathy, and credibility needed to lead much larger organizations. In fact, according to a report from Spencer Stuart, 76% of sitting S&P 500 CEOs in its 2025 study had been promoted from within their companies.
- Mary Barra, General Motors: Barra joined GM at 18 as a co-op student inspecting vehicles. “I learned that working on an assembly line is hard work and the people that do it are talented.”
- Raj Subramaniam, FedEx: The FedEx CEO started off in an entry-level marketing role. “I started off as an associate marketing analyst in the international division in Memphis. That job is the lowest level in marketing.”
- Doug McMillon, Walmart: McMillon got his start by unloading trucks before rising through Walmart. “I became a low-risk promotion because people had already seen me do the job.”
- Bob Iger, Disney: Iger credited his early ABC production roles with developing a lasting professional discipline. “I discovered that I had in me … a prodigious work ethic, which I think has never left me.”
Sources: Duke Today, Time, Business Insider, and Vogue.
AI job simulators could create major winners and hidden costs
For investors, the big opportunity, at least in the long term, is that businesses could turn workplace knowledge into scalable software.
Naturally, the potential returns could be attractive, as simulators could shorten employee ramp-up periods, slash coaching expenses, and reduce costly errors while improving consistency on the customer service side.
However, the real moat would depend largely on developing robust proprietary scenarios, integrating with corporate systems, ensuring reliable scoring, and demonstrating that simulated performance equals better real-world results.
For consumers, that could mean better-prepared employees and more consistent service. Or it might result in poorly designed simulations that could scale bad advice, biased scripts, or regulatory errors across an entire workforce.
On the other side of the equation, workers might gain private, repeatable practice without the embarrassment or consequences of making mistakes in front of customers or managers. Yet the downsides include opaque scoring, as highlighted by the recent claims in the Meta Platforms lawsuit, reduced access to human mentors, and greater pressure to train outside paid working hours.
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This story was originally published July 26, 2026 at 6:03 AM.