Managing Director, Individual Tax and Strategy Services

Managing Director

Individual Tax and Strategy Services

Firm Overview:

Stable Rock is an integrated professional services platform supporting over 500 clients including investment and asset managers, early-stage and midsize businesses, portfolio companies, and founders. We provide deep expertise across outsourced and fractional CFO services, accounting and bookkeeping, middle office and operations, regulatory and compliance, tax strategy and planning, IT, HR, insurance services, and AI-driven automation.

Our work is hands-on and customized. Clients work directly with a team of experienced professionals who take the time to understand how their business or personal finances operate and provide practical support that adapts as needs change.

Job Opportunity and Responsibilities:

Stable Rock is seeking a Managing Director, Individual Tax & Strategy to lead our individual tax practice, serving a sophisticated client base of high-net-worth individuals with complex tax and investment profiles. This senior-level role will oversee tax return preparation and review, provide year-round tax planning and investment-related guidance, and serve as a trusted advisor on complex tax matters.

The Managing Director will lead and develop a team of tax professionals, maintain high standards of technical accuracy and client service, and help strengthen and expand the practice. This role is ideal for an experienced tax leader who combines deep individual tax expertise with strong client advisory skills and a commitment to building scalable, high-quality service delivery.

Key Responsibilities:

Individual Tax Compliance & Technical Oversight

• Oversee the preparation, review, and final approval of complex individual income tax returns, including federal and state filings.

• Review returns for accuracy, completeness, technical compliance, and appropriate application of tax laws and regulations.

• Provide technical guidance on investment income, W-2 compensation, K-1s, private equity and other alternative investments, and complex multi-entity investment structures.

• Resolve complex tax issues, research technical questions, and ensure appropriate documentation and compliance standards.

• Establish and maintain quality control procedures, review standards, and efficient tax preparation processes.

Tax Planning & Client Advisory

• Serve as a trusted advisor to high-net-worth individuals on tax planning, tax-efficient investment strategies, and complex financial matters.

• Provide year-round guidance on the tax implications of investment activity, liquidity events, portfolio changes, and other significant financial decisions.

• Field client questions, explain tax positions and potential implications, and recommend practical strategies aligned with each client's circumstances.

• Collaborate with clients' investment managers, financial advisors, attorneys, and other professional advisors as appropriate.

• Proactively identify tax planning opportunities and help clients navigate changing tax regulations and reporting requirements.

Team Leadership & Practice Management

• Lead, mentor, and develop a team of tax managers and other professionals, providing technical direction and oversight.

• Manage workloads, review cycles, deadlines, and resource allocation to ensure consistent, timely delivery of high-quality client work.

• Build a culture of accountability, collaboration, continuous learning, and exceptional client service.

• Identify opportunities to improve workflows, leverage technology, and scale service delivery as the practice grows.

• Support the continued development of Stable Rock's individual tax and advisory capabilities, including service expansion and team growth.

Client Relationships & Business Growth

• Develop and maintain strong, long-term relationships with clients through responsive service, sound judgment, and proactive communication.

• Identify opportunities to deepen existing client relationships through additional tax planning and advisory services.

• Partner with other Stable Rock service lines to deliver coordinated solutions for clients with complex financial and business needs.

• Contribute to the continued growth and evolution of the practice, with an emphasis on service quality, client retention, and operational excellence rather than direct business development quotas

Qualifications, Skills, and Experience:

• CPA required.

• 12+ years of progressive tax experience, including significant experience in individual tax compliance, planning, and advisory services.

• Demonstrated expertise preparing and reviewing complex individual tax returns for high-net-worth and ultra-high-net-worth individuals.

• Strong technical knowledge of investment income, partnership and S corporation K-1s, private equity and alternative investments, and related tax reporting considerations.

• Experience providing year-round tax planning and advising clients on the tax implications of investment and financial decisions.

• Proven ability to review and sign off on complex returns, resolve technical issues, and maintain high standards of accuracy and compliance.

• Prior experience leading and developing tax managers and other tax professionals.

• Excellent client communication skills, sound professional judgment, and the ability to translate complex tax matters into clear, actionable guidance.

• Strong organizational, analytical, and process improvement skills, with the ability to manage competing priorities and seasonal deadlines.

• Experience in a public accounting, tax advisory, family office, or other professional services environment preferred.

Why Stable Rock

At Stable Rock, you'll have the opportunity to combine deep technical expertise with meaningful client relationships in a collaborative, entrepreneurial environment. We take a hands-on approach to solving complex challenges, providing tailored tax and advisory services that help our clients make informed financial decisions.

As a senior leader, you'll play a key role in shaping the growth of our individual tax practice, developing talented professionals, and expanding the value we deliver to high-net-worth clients. You'll have the opportunity to influence processes, strengthen our service offerings, and collaborate across disciplines while maintaining a strong focus on technical excellence and client outcomes.

We value initiative, thoughtful problem-solving, and a commitment to continuous improvement. At Stable Rock, your expertise will have a direct impact on our clients, our team, and the continued evolution of our business.

Location

We are open to exceptional talent nationwide, with a strong preference for candidates located in or near our core markets: New York, Dallas, Miami, Chicago, San Francisco, and Los Angeles.

Compensation

Highly competitive base salary ranging from $200,000 to $250,000, based on experience and location, with eligibility for a discretionary performance bonus.

Benefits

• Medical, Dental, and Vision insurance coverage. Employee-only premiums are paid at 100%.

• Health Savings Account (HSA) and Flexible Spending Account (FSA) options

• 401(k) retirement savings plan

• Unlimited paid time off policy

• Hybrid work flexibility to support professional and personal balance

Inclusion

Stable Rock is an equal opportunity employer and we value diversity at our firm. We do not discriminate on the basis of race, religion, color, national origin, gender, sexual orientation, age, marital status, veteran status, or disability status. We encourage candidates from all backgrounds to apply and are committed to building a team that reflects many different perspectives and experiences.

Applicants in need of special assistance or accommodation during the interview process or in accessing our website may contact us. We will treat your request as confidentially as possible. In your email, please include your name and preferred method of contact, and we will respond as soon as possible.