Stephen Oldfield

Scaling and stabilizing a statewide transportation program

I took over one of the largest coordinated human-service transportation programs in Massachusetts — the system that gets people to dialysis, to chemotherapy, and to behavioral health appointments when they have no other way to get there. It is not an abstraction. When it fails, somebody misses treatment.

What I found was five functions operating as five functions: operations, compliance, finance, technology, and vendor oversight, each competent, none connected. So I connected them into one management system — clearer operating rhythms, performance visibility that a person could actually read, governance that made accountability land somewhere specific, and a vendor network that knew what the standard was and what happened when it wasn't met.

The unglamorous half of that work was the numbers. Before I would brief a figure, it had to reproduce the officially reported one exactly — not approximately. That is the least interesting sentence on this page and it changed more than anything else I did.

Modernizing a contact center with AI, carefully

High-volume contact center, regulated service environment, and an access problem: people who needed a ride were waiting on a phone line to get one. We replaced the telephony and deployed an interactive virtual attendant with English and Spanish self-service, so the routine requests stopped queueing behind the complicated ones.

The technology was the easy part. The work was everything around it — how it changed staff workflow, what quality assurance looked like when a machine handled the first minute of a call, where the handoff to a human had to be guaranteed rather than encouraged, and which categories of call were never allowed near an automated path at all. In a regulated environment you do not get to ship a customer-service experiment and see how it goes.

I have outcome figures for this work. They came from an internal system, they have not been through a confidentiality and accuracy review, and until they have, they stay off this page.

Taking the enterprise

Moving from running a function to running the organization is not more of the same job. I went from a program I knew intimately to transit, paratransit, mobility, the statewide brokerage, capital, finance, regulatory, technology, and workforce — most of which I had opinions about and some of which I had to learn in public, during a leadership transition, while the buses still had to run.

What I set first was not a strategy. It was the expectations: trust, accountability, transparency, teamwork, and the assumption that the person closest to the work usually knows something you don't. I expect a lot from a team and I back them fully — those aren't in tension, they're the same move. High standards without support is just pressure. Support without standards is just comfort. Neither one builds an organization anybody is proud of.