Engagement Director

Why Join Cunningham & Associates

Most tax firms are built around transactions. Cunningham & Associates is built around relationships, responsibility, and results. If you've built your career in compliance-heavy environments and are ready for a role focused on advisory, leadership, and client ownership, this opportunity was designed for you. We exist to empower businesses and elevate lives by serving as our clients' primary, accountable advisor — not just their tax preparer.

Our clients expect more from their professional relationships, and we've accepted the responsibility to deliver proactive planning, coordinated advice, and an exceptional client experience year after year. As we continue to grow our Private Tax & Advisory practice, we are expanding our leadership team with experienced professionals ready to step into a client-facing, relationship-driven Engagement Director role. The Tax Director role is equivalent to — and a progression beyond — a traditional Tax Manager position.

This is an opportunity for tax leaders who want to move beyond doing returns and into owning client relationships, guiding strategy, and being part of a dynamic team.

Cunningham & Associates is a private tax and advisory firm designed to function like a private family office for business owners and high-net-worth families.

• Serve as the central point of coordination for tax, financial, valuation, and strategic planning
• Blend technical excellence with an exceptional human touch
• Operate as a results-based, fixed-fee firm — if we don't perform, we don't get paid
• Build long-term relationships that extend across business cycles and life stages

• Amazing client experience
• Strategic tax planning
• Advanced financial and valuation services
• A relentless commitment to excellence and growth

Tax & Engagement Directors do not operate in silos. You are supported by:

• A dedicated back-office team handling preparation and technical execution
• Practice area leadership and structured review processes
• Clear systems, standards, and defined scopes

This structure allows our Tax & Engagement Directors to focus on where they add the most value: clients, planning, leadership, and opportunity identification — not grinding through technical work.

The Tax Director role is a leadership position and a natural progression for experienced tax professionals who want greater client ownership, influence, and impact. This role is not about preparing returns. It is about:

• Leading client relationships
• Managing engagement scope and expectations
• Driving planning conversations
• Reviewing and guiding work prepared by a dedicated back office
• Identifying additional advisory opportunities

• Serve as the primary point of contact for assigned clients
• Lead annual and ongoing tax planning and advisory conversations
• Manage engagement scope, deliverables, and client expectations
• Review work prepared by internal teams for accuracy and alignment
• Coach and develop team members through review and training
• Identify opportunities for expanded tax, financial, and valuation services

Success is measured by client outcomes, relationship depth, and long-term value — not hours billed or returns processed.

• Emphasis on relationship management and strategy, not volume compliance
• Dedicated back office handling preparation and execution
• Fixed-fee, results-based advisory model
• Clear expectations, systems, and leadership support
• Opportunity to build long-term client relationships and advisory depth

Role:
This is not a traditional role, and as such, we are looking at candidates who might come with an Audit Manager, Tax Manager, or Fractional CFO background. Additionally:

• 5+ years of experience in tax or related advisory roles
• Active credential required:
  Certified Public Accountant (CPA), or Enrolled Agent (EA), or Certified Valuation Analyst (CVA)
• Strong client-facing communication skills
• Desire to lead, review, and plan — not just execute

• Targeting candidates located in New England
• Flexible office…