Stephen Oldfield

About Stephen Oldfield

I’m a team-first leader who believes strong organizations are built by people who are willing to lead from the boardroom and the front line. My work centers on operations, technology, and building systems that allow teams to succeed in complex, high-accountability environments. I’m comfortable in strategic conversations with executives and boards, but I’m just as comfortable rolling up my sleeves with the team to solve problems, improve processes, and move the work forward. I specialize in stabilizing high-pressure, high-compliance environments and turning them into disciplined, measurable operations supported by strong teams and clear systems.Today I serve as Administrator-CEO of the Montachusett Regional Transit Authority (MART), where I oversee both transit operations and the statewide Human Service Transportation brokerage. The brokerage coordinates millions of MassHealth transportation trips each year through a network of more than 375+ transportation providers across Massachusetts, helping connect residents to healthcare and medical appointments.Before becoming Administrator, I served as Executive Director of Brokerage, leading the Commonwealth’s largest Human Service Transportation brokerage and supporting roughly 6+ million trips annually. Operating at that scale reinforced something I believe strongly: good outcomes come from clear expectations, disciplined processes, and teams that are trusted and supported to do their work well.My leadership style is practical and hands-on. I focus on building the operating rhythm of an organization — clear metrics, straightforward communication, common sense decision-making, and a culture where people are trusted, supported, and held to a high standard.A big focus of my work today is modernizing how organizations operate. I use data, automation, and emerging technology to reduce friction, strengthen oversight, and improve service delivery. If it doesn’t actually improve outcomes, it’s probably not worth doing.Earlier in my career I worked in the private sector in market research operations, working my way from intern to Chief Operating Officer at a national research firm. That experience shaped how I approach leadership today: take ownership, be honest about problems, invest in people, and build systems that hold up over time.At the end of the day, I’m motivated by work that matters — building organizations people can rely on, teams people are proud to be part of, and public services that actually work the way they’re supposed to.

Experience

1. Administrator CEO

   Montachusett Regional Transit Authority

   Jan 2026 — Present · Leominster, MA, US

   Appointed Administrator overseeing all agency operations, including fixed-route transit, paratransit, and Human Service Transportation brokerage functions. Serve as chief executive responsible for agency strategy, operational performance, financial stewardship, regulatory compliance, technology modernization, and long-term planning across a complex public transportation system.Accountable to the Board for service reliability, fiscal discipline, and regulatory integrity, including compliance with FTA, state, and contractual requirements. Lead executive leadership team and department heads, establishing clear expectations, performance standards, and operating cadence to ensure disciplined execution and transparent decision-making.Drive modernization and operational improvement initiatives focused on data-informed management, system reliability, vendor oversight, and scalable technology solutions. Balance public service obligations with operational efficiency, risk management, and workforce development to strengthen outcomes for riders, employees, partners, and the communities served.

Education

• Fitchburg State University

  Master of Business Administration (M.B.A.), Business Management

  2014 — 2016

• Cushing Academy

  High School

  2004 — 2008

• Fitchburg State University

  B.A, Business Management

  2009 — 2012