Director of Tax

Clearstead is seeking an experienced Tax Manager to lead and support comprehensive tax planning, compliance, research, and advisory services for high-net-worth individuals, families, trusts, estates, partnerships, corporations, and clients of a Registered Investment Adviser platform. Based in Portland, Maine, this role will serve as a senior tax resource for the Portland office while also providing tax leadership, technical support, and client service coordination for the Philadelphia office.

• Lead the preparation, review, and delivery of complex tax work across individual, partnership, corporate, trust, estate, gift, and related tax matters.
• Manage and review individual, partnership, corporate, trust, estate, gift, and related tax returns for high-net-worth individuals, families, executives, business owners, and complex client relationships.
• Oversee comprehensive tax planning and compliance work within an RIA environment, including coordination with wealth advisors, financial planners, investment teams, trust administrators, estate planning professionals, and outside counsel as appropriate.
• Research and analyze complex federal, state, local, fiduciary, gift, estate, and multi-jurisdictional tax matters and translate technical findings into practical recommendations for clients and internal teams.
• Serve as a point of contact for tax authorities, client inquiries, notices, audits, estimates, extensions, and other tax-related matters.
• Provide leadership, coaching, and review support to tax associates and other team members to ensure accuracy, consistency, professional development, and timely completion of work.
• Support the Philadelphia office by assisting with tax workflow management, client service needs, technical research, and collaboration across offices to deliver a consistent Clearstead client experience.
• Identify planning opportunities, tax risks, process improvements, and cross-functional issues that should be elevated to senior tax leadership and client advisory teams.
• Contribute to special projects, process improvements, integration initiatives, and firmwide efforts to align tax services across Clearstead’s regional offices.

• Bachelor’s degree in accounting, finance, taxation, or related field; advanced degree in taxation preferred.
• 10+ years of progressive tax experience, preferably including public accounting, private wealth, family office, trust/estate, or RIA-related tax experience.
• CPA, EA, or equivalent professional credential strongly preferred.
• Deep technical knowledge of federal, state, local, fiduciary, estate, gift, and multi-state tax regulations and compliance requirements.
• Demonstrated experience with all aspects of tax work for clients of an RIA, including tax planning, tax compliance, estimated taxes, projections, notices, research, client communications, and coordination with investment, planning, and estate professionals.
• Experience managing complex client relationships and communicating tax concepts clearly to clients, advisors, and internal stakeholders.
• Ability to lead, coach, review, and develop team members while managing deadlines and maintaining high-quality work product.
• Strong computer skills, including Microsoft Office and relevant tax preparation, research, workflow, and document management systems.
• Strong interpersonal, oral, and written communication skills, with the ability to collaborate effectively across Portland, Philadelphia, and other Clearstead offices.
• Strong analytical, organizational, project management, and critical thinking skills.
• Strong time management skills and the ability to manage competing priorities during peak tax seasons and client deadlines.
• Exceptional attention to detail, sound judgment, discretion, and commitment to client service excellence.

Clearstead is a financial advisory firm serving wealthy families and leading institutions. Our mission is to enable wealthy families and leading institutions to meet their financial objectives and achieve their aspirations, building stronger futures for their families, their communities, and themselves.

We fulfill our mission by creating a unified investment framework for our clients and integrating financial planning, tax planning and compliance, trust administration services with investment management to address complex financial situations.