Tax Director

Join a Team That Thinks Taxes Are Fun (Seriously.)

At TSG Your Trusted Accountant , we're not your average accounting firm. We're a collaborative crew of CPAs and tax planners who genuinely enjoy solving tax puzzles. To us, every tax return is a challenge worth mastering and we find joy in untangling last year's messes, strengthening small businesses, and uncovering tax savings along the way.

As Westbrook's largest full-service tax, accounting, and consulting firm, we're proud to be a Next Generation Accounting Firm . That means we focus on relationships over transactions, strategic guidance over cookie-cutter forms. We offer forward-thinking counsel to help small businesses grow, while also delivering excellent traditional tax prep services.

Led by a self-made, female entrepreneur, our team blends decades of expertise with fresh perspectives. We're casual, collaborative, and serious about delivering top-tier service without sacrificing fun or flexibility.

About the Role: Tax Director

We're searching for an ambitious and growth-minded Tax Director to step into a high-impact leadership role. If you're someone who thrives on solving complex problems, enjoys client interaction, and wants to help shape the future of a firm this is your chance.

You’ll join a culture that respects your time and encourages your development, with unmatched flexibility, meaningful work, and a team you’ll actually enjoy working with.

What You’ll Bring

You’ll be a strong fit for this role if you:

• Have at least 10 years of experience preparing and reviewing tax returns across a wide range of entities - individual, corporate, partnership, estate/trust, and nonprofit.


• Have experience supervising and mentoring staff.


• Stay current on evolving tax laws and enjoy educating others.


• Excel in a collaborative, team-driven environment.


• Build and maintain strong client relationships.


• Are excited to live and work in beautiful coastal Maine, just minutes from the vibrant foodie scene of Portland. (Our newly renovated, dog-friendly office sits on Main Street in Westbrook, across from the Presumpscot River!)

Compensation & Perks

We believe your compensation should grow with your impact:

• No need to bring in new business we have plenty of work and will match it to your interest and capacity.


• Start with ~$400K in client work with room to grow.


• Base pay starting at $150,000

Plus, Outstanding Benefits:

• Unlimited PTO and make-your-own-schedule flexibility


• 401(k) with 3% match


• Health and dental insurance


• Short- and long-term disability coverage


• Group life insurance


• Ongoing training and professional development

If you love the idea of turning tax puzzles into solutions and want a role that respects both your talent and your time we'd love to meet you.

Our goal is to ESOP by December 31, 2030.