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 Engagement 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

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 Engagement Directors to focus on where they add the most value: clients, planning, leadership, and opportunity identification -- not grinding through technical work.

The Engagement Director role is a leadership position and a natural progression for experienced tax professionals who want greater client ownership, influence, and impact.

• 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

Engagement Directors operate as the quarterback for their clients -- supported by strong internal systems and technical teams.

• 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

• 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 schedule and geographic flexibility for the right candidate

Base Salary + Retention Bonus

• 50% paid after successful completion of the 90-day probationary period
• 50% paid at the one-year anniversary

• Eligibility for the firm's incentive and profit-sharing program
• Additional compensation potential estimated at $25,000 - $50,000+ annually, based on performance, client relationships, and firm growth

• Additional compensation opportunities tied to continued professional development, advanced credentials, and expanded areas of expertise
• Ongoing investment in leadership development and advisory skill building

• Engagement Directors are viewed as long-term leaders within the firm
• As the firm continues to grow, Engagement…