Engagement Director

Why Join Cunningham & Associates

Cunningham & Associates is built around relationships, responsibility, and results. We empower businesses and elevate lives by serving as our clients' primary, accountable advisors. Our clients expect more from their professional relationships, and we accept the responsibility to deliver proactive planning, coordinated advice, and an exceptional client experience.

About the role

The Tax Engagement Director role is equivalent to and a progression beyond a traditional Senior Tax or 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.

Opportunity Overview - Tax Engagement Director

Tax Engagement Directors do not operate in silos. They 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 Tax Engagement Directors to focus on where they add the most value: clients, planning, leadership, and opportunity identification—not grinding through technical work.

Key Responsibilities

• 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

What Makes This Role Different

• 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.

Experience & Credentials

• Role: Not a traditional role, looking for candidates with Senior Tax, Tax Supervisor, Tax Manager, or Fractional CFO background.
• Active credential required: CPA, EA, or CVA.
• Strong client-facing communication skills.
• Desire to lead, review, and plan—not just execute.

Location & Flexibility

Targeting candidates located in New England. Flexible office schedule and geographic flexibility for the right candidate.

Compensation, Growth & Long-Term Opportunity

• Base Salary + Retention Bonus: 50% paid after successful completion of the 90-day probationary period, 50% paid at the one-year anniversary.
• Incentive & Profit Sharing (Beginning After Year 1): 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.

Professional Development & Credential 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.

Career Progression & Partnership Opportunity

• Engagement Directors are viewed as long-term leaders within the firm.
• The firm continues to grow, Engagement Directors play a central role in shaping client relationships, developing future leaders, and expanding the firm's advisory platform.
• High-performing Engagement Directors who demonstrate leadership, relationship ownership, and sustained impact have a path to senior leadership and potential partnership.

Who Thrives Here

• This role is not a fit for professionals who prefer purely technical work or limited client interaction.
• This Role Is Ideal For Professionals Who Enjoy building deep, trusted client relationships,
• Think strategically and proactively,
• Want ownership and leadership responsibility,
• Are ready to move beyond traditional tax manager roles.

Next Steps

If this opportunity resonates, we invite you to apply and start the conversation. Learn more about our firm at www.jec-llc.com.