CEO, Engageware // Serial Fintech Builder
Dan
O'Malley
He doesn't disrupt banks. He builds the software they wish they already had - then does it again.
The repeat operator, at ease
He doesn't disrupt banks. He builds the software they wish they already had - then does it again.
The repeat operator, at ease
In September 2025, Dan O'Malley took the corner office at Engageware - the AI-powered customer engagement platform built for large, regulated enterprises. Banks, credit unions, healthcare systems. The kind of organizations where "move fast and break things" gets you a regulatory letter.
That suits him. O'Malley has spent more than two decades learning to make slow, careful institutions move like software companies. Engageware's pitch is three things stitched together: AI agents, appointment scheduling, and knowledge management, trusted by more than 600 customers. His job is to push all three deeper into the AI era without spooking the compliance department.
"I'm excited to join Engageware at such a pivotal moment for the industry," he said on arrival. The line is modest. The track record behind it is not.
Engageware's platform powers streamlined interactions for our customers with their customers, uniquely addressing the requirements of large, sophisticated, and regulated enterprises.- Dan O'Malley, on joining Engageware
Most fintech founders define themselves against banks. O'Malley keeps choosing to build with them, from the inside, and the most telling proof is Numerated.
In 2014 he joined Eastern Bank - a New England institution older than two centuries - as Chief Digital Officer, and co-founded Eastern Labs, its innovation arm. The mandate: keep an old bank competitive against the fintechs nipping at it.
Numerated did not start as a startup. It began as a project inside that lab, then was carved out as an independent company in 2017, built to help banks grow relationships faster with a real-time, AI-driven lending platform.
By 2024, Numerated served institutions representing roughly $4 trillion in assets and had powered more than $70 billion in commercial lending. Moody's (NYSE: MCO) bought it, folding it into the Moody's Lending Suite.
The career makes more sense once you see the degree. O'Malley studied Operations Research and Financial Engineering at Princeton, graduating in 2000. Not finance. Not pure computer science. The discipline that sits between them - turning messy real-world systems into math you can optimize.
It is a useful lens for everything that followed. A neobank is an optimization problem. A bank's lending desk is an optimization problem. So is routing a customer to the right answer at the right moment, which is roughly what Engageware sells.
He co-founded a neobank around 2008 - years before the word existed.PerkStreet bet consumers would bank entirely online. They were early.
Dan brings a history of leading successful software companies, deep domain expertise in the financial services market, and a successful track record of accelerating growth through a customer-centric approach.- Michelle Noon, founder, Clearhaven Partners
Dan is a proven leader with strategic and operational insight and a track record of driving growth.- Rick Lowrey, Executive Chairperson, Engageware
O'Malley's aim at Engageware is the same move he has made before, scaled up: take practical AI - agents, scheduling, knowledge - and turn it into measurable growth for the kind of large, regulated enterprises everyone else finds too hard to sell to. He has spent a career proving that the careful, complicated institutions are exactly where the interesting software gets built.