Wall Street is paying $25,000 a day for AI trainers who used to work there

The business move

Two former investment bankers, Felipe Sinisterra and Dave Wang, are charging Wall Street firms up to $25,000 a day to teach senior staff how to use AI tools they have already purchased. Their calendars are booked solid for the next two months, as banks and investment funds scramble to get practical training in applying AI effectively. The demand reflects a gap between buying AI software and knowing what to do with it.

Why it matters

Financial institutions have spent heavily on AI technology, but many still lack the expertise to integrate it into critical workflows and decision-making. Training from insiders with investment banking experience bridges this divide, making AI adoption less theoretical and more operational. This scenario puts a price tag on the skills needed to turn AI spending into real business value and raises the cost of adoption by outsourcing implementation know-how at a premium. It also underscores the urgency for firms to build internal AI competencies rather than rely on high-priced external consultants.

Who gains and who gets squeezed

Sinisterra and Wang gain by leveraging their unique blend of AI knowledge and financial sector backgrounds, commanding premium rates for practical training that banks cannot easily replace. Financial firms face squeezed margins as they pay top dollar for AI learning after already investing in the technology. Middle managers and staff are pressured to learn quickly while senior leaders have to justify these expensive consulting fees against uncertain outcomes. Vendors supplying AI tools benefit indirectly as firms increasingly rely on trainers to realize promised efficiencies.

What to watch next

Watch for increased demand for hybrid AI-finance talent and whether firms begin developing in-house AI trainers to cut costs. Also monitor if this trend shifts vendor strategies—such as bundling training or simplifying AI tools to reduce dependence on pricey experts. Finally, keep an eye on how quickly Wall Street’s AI capabilities mature as this training push either accelerates adoption or exposes a skills bottleneck slowing down AI’s impact on finance operations.

AI Quick Briefs Editorial Desk