About O'Brien, Riley & Ryan, CPA O'Brien, Riley & Ryan, CPA is a team of more than 20 professionals serving high-net-worth individuals, trusts and estates, real estate investors and closely held businesses, with returns filed in more than 40 states. The firm and its predecessors have served clients for more than 60 years, on three principles: professionalism, responsiveness and quality. We are in the middle of a full transformation into a next-generation professional services firm. That means one practice management platform for every client, hosted systems, a modern client portal, and AI built into how we work every day. We use Claude and comparable AI tools to research, draft, review and automate, so our people spend their time on judgment and client relationships rather than manual work. We are moving into a brand-new, state-of-the-art 5,000 square foot headquarters at Braintree Hill Office Park. Our clients come to us for tax compliance, year-round tax planning and advisory programs, and fiduciary and estate work. If you want to help build a modern firm rather than maintain an old one, we would like to hear from you. The role We are adding a Tax Supervisor to take complex returns from preparation through first review and to lead a small team of staff accountants. You will report to our Tax Managers.

The work runs year round:

heavy preparation and review from February 1 to April 15 and from September 1 to October 15, and tax projections, planning and advisory support the rest of the year. What you will do Prepare and first-review individual, fiduciary and pass-through returns: 1040, 1041, 1065 and 1120-S, including multistate Supervise and train staff accountants, and manage their work through TaxDome Prepare tax projections and planning workpapers for the Tax Managers and partners Handle estimates, extensions and notices for an assigned group of clients Use Claude or comparable AI tools every day for research, review checks, workpapers and client communication, and verify every output What you bring (required) Active CPA license, Massachusetts or a state that qualifies for Massachusetts practice privilege Five or more years of public accounting tax experience, including one or more years reviewing others' work Individual, fiduciary and pass-through return experience Preparation and review experience in UltraTax CS, CCH or Lacerte Hands-on use of AI tools to work faster and more accurately, with the judgment to check what they produce Clear written communication with clients and staff Preferred 706 and 709 experience Trusts and estates, real estate and closely held business clients A record of training and developing staff Our technology Microsoft 365, TaxDome practice management and client portal, UltraTax CS on Verito hosted desktops, Zoom Phone, QuickBooks Online, and Claude as our AI platform. Pay and benefits $105,000 base salary plus an annual bonus of 10% of base Full benefits package: medical insurance from the first of the month after your start date, and a 401(k) with an employer match after three months of service Hybrid schedule, three to four days a week in our new Braintree headquarters Start in November or December 2026 The position is with O'Brien, Riley & Ryan, CPA. Our employer of record is State Street Business Services LLC. O'Brien, Riley & Ryan, CPA is an equal opportunity employer. We consider all qualified applicants without regard to race, color, religion, sex, sexual orientation, gender identity, national origin, age, disability, genetic information, veteran status or any other characteristic protected by law. It is unlawful in Massachusetts to require or administer a lie detector test as a condition of employment or continued employment. An employer who violates this law shall be subject to criminal penalties and civil liability.

Pay:

$105,000.00 per year

Benefits:

401(k) 401(k) matching Health insurance Application Question(s): Describe a task you now do with AI. What did it replace, how do you check the output, and what time did it save?

Experience:

Public accounting tax: 5 years (Required)

License/Certification:

CPA (Required) Ability to

Commute:

Braintree, MA 02184 (Required)

Work Location:

Hybrid remote in Braintree, MA 02184