Why Capital One's 'Why' Matters for Fintech Execution Risk

Every financial institution talks about transformation. The technical work gets the headlines. The organizational work determines whether initiatives succeed or stall. Jay Michelini, vice president of product at Capital One Business, told PYMNTS that successful change management starts before any software reaches production. Leaders must first make sure employees understand why change is happening.

“You’ve got to lead with the ‘why,’” Michelini said.

He argued against relying solely on executive messaging. Organizations benefit when they identify employees who are genuinely interested in a particular initiative and can explain its practical value across the business. Internal champions often carry more credibility than formal announcements, whether the subject is product modernization or a new payments capability.

Ownership also depends on showing employees how their work affects people beyond their immediate teams. Michelini described three perspectives that help create that connection: understanding customer needs firsthand, appreciating how operational colleagues experience day-to-day work, and recognizing how competitive developments across the fintech sector reshape expectations. Each offers a different reason for embracing change, making the discussion less abstract and more closely tied to daily responsibilities.

Michelini encouraged product leaders to spend time with customers and internal stakeholders rather than relying exclusively on reports or dashboards.

“I just spent time visiting with our sales team … It was so eye-opening to sit with them firsthand,” Michelini said. “You see different angles to a problem … You need to have conviction in the direction that you’re heading but be open to different perspectives and feedback that are going to change your mind or adjust your course of travel.”

Organizational change frequently falters when departments work independently rather than together, Michelini said. Instead of treating product, technology, operations, compliance and other functions as sequential checkpoints, leaders should use them to shape decisions from the outset. He suggested leaders ask simple questions during project reviews: Were operational teams consulted early? Have legal and risk partners already weighed in? Is this the first time an executive stakeholder is hearing about a significant initiative? These signals reveal whether teams have been solving problems collectively or merely handing them to someone else.

Managers should also reconsider how they measure progress during periods of change, Michelini said. Delivery schedules and performance metrics remain important. They rarely capture whether a team is under unnecessary strain or whether obstacles are beginning to undermine morale. He recommended shifting the question from “Where is it?” to “How do you feel about how progress is going?” That framing exposes issues traditional reporting overlooks. Teams may be meeting deadlines while relying on excessive overtime or waiting for decisions from other parts of the organization. These conversations help leaders identify where they can remove obstacles instead of merely monitoring them.

Cross-functional partners offer another useful perspective because they work across multiple initiatives simultaneously, Michelini said. Legal, compliance, risk and product specialists can quickly identify where collaboration is working and where projects are creating avoidable friction.

“I think about creating missionaries, not mercenaries,” Michelini said. “It’s very important to empower the teams to outthink you.” He added, “I don’t have all the answers.”

The readthrough for the financial sector is straightforward. Banks and fintechs undertaking digital transformation face the same organizational pitfalls. Firms that manage change well reduce turnover, accelerate adoption, and lower the cost of stalled projects. Those that ignore the human side of transformation burn through talent and miss deadlines. For investors tracking stock market analysis, the quality of internal change management is a leading indicator of whether a digital strategy will deliver on promises. Michelini’s emphasis on listening before launching, measuring team health alongside milestones, and bringing cross-functional partners in early offers a practical checklist for evaluating execution risk. The philosophy echoes a broader theme: speed without alignment creates noise, not progress. Why Drucker's 'Do The Right Things' Beats Speed in Markets makes a similar case for measured, purpose-driven decision-making.

Capital One Financial (COF) has invested heavily in its business banking platform. Michelini’s comments suggest that the internal culture at Capital One Business is built around collaboration and open feedback. Whether that culture survives scaling and competitive pressure is a variable worth watching.