Page 44 - BusinessWest April 27, 2026

Tom Dowling
Partner-in-Charge, Holyoke, Whittlesey:
Age 39
Tom Dowling says he’s always been drawn by the
variety of work offered by the broad realm of public
accounting.
By that, he meant the wide range of business sectors
as well as the diverse nature of individual companies
and nonprofits he gets to work with — especially the
latter.
Indeed, Dowling, partner-in-charge for Whittlesey’s
Holyoke office, manages a large book of clients, many of
them nonprofits, for which he has become a trusted advisor,
providing services that go well beyond tax and audit work.
“He guides them through regulatory changes, funding
changes, and leadership changes,” wrote Drew Andrews,
Whittlesey’s CEO and managing partner, who nominated
Dowling for the 40 Under Forty. “As Massachusetts nonprofits
face more financial pressure, Tom’s advice goes beyond audits;
he helps clients find new funding, improve internal controls,
work more efficiently, and build long-term financial plans.”
These sentiments help explain why Dowling was drawn to
public accounting, and why he is a rising star in this field. But
there’s more to the story.
Indeed, he came to Whittlesey in 2017 and played a key role
in its merger with the Holyoke-based firm Lester Halpern and
then in strengthening the Hartford-based firm’s presence in
Western Mass. and growing market share in this region.
He was named partner in 2022 and now oversees the
Holyoke office and its staff of 20.
His portfolio of clients is diverse, but, as he noted,
one of the focal points — for him and the firm — is
nonprofits, which are now facing ever-rising levels of
uncertainty and challenge.
“This year has been busy with the current
developments in the political landscape — it seems
like every other day, there’s something that’s changing
and impacting a nonprofit or creating some uncertainty
in their funding,” Dowling said. “And we are constantly in
discussions with all of our clients to make sure they’re
aware of these issues and that they know how to assess
and react if needed.”
Active within the industry — he’s a member of the
American Institute of CPAs, the Massachusetts Society of
CPAs, and the Assoc. of Certified Fraud Examiners, among
other groups — he is also busy in the community, especially
as a committee member for the Make-A-Wish Massachusetts
and Rhode Island Swish Night event, but also as a youth
basketball coach.
“I’ve been coaching my kids since they were able to play,” he
said, referring to sons Carter, 14, and Wesley, 8. “It’s one of my
favorite times of the year, and it’s nice to see the kids grow.”
—George O’Brien
ASSURANCE | ADVISORY | TAX | TECHNOLOGY
Whittlesey congratulates our own
Tom Dowling
and all the Business West 40 Under
Forty Class of 2026 recipients.
Tom’s commitment to our clients
has helped them successfully
navigate compliance, economic,
and technological changes
to see a better future.
14 Bobala Road, 3rd Floor, Holyoke, MA 01040
413.536.3970 | www.WAdvising.com
A22 2026
Business W est