Director, Tax Strategy

Job Details

Level
:
Experienced

Job Location
:
Chicago Office - Chicago, IL 60606

Salary Range
: $ - $ Salary/year

Cresset is a firm built by clients, for clients. As an independent, award‑winning multi‑family office and private investment firm, we are reimagining the way wealth is experienced. Our purpose is to help ensure that both wealth and life are fully optimized—integrated, intentional, and aligned with each client’s vision of success.

We provide access to the caliber of talent, ideas, and investment opportunities typically available to the largest single‑family offices and institutions. Our approach is personalized, entrepreneurial, and client‑first.

Proudly owned by our clients and employees, Cresset was built to endure. We are creating a 100+ year firm—one focused on delivering an exceptional experience, not only for the families we serve but for the team that serves them. Recognized by Barron’s and Forbes among the nation’s top RIA firms, and as one of the industry’s best places to work, Cresset is guided by long‑term relationships, shared success, and a belief that wealth should serve a life well lived.

Cresset is seeking a Director of Tax Strategy to join our Tax Strategy team. This is a high‑impact, client‑facing advisory role focused exclusively on sophisticated income tax planning for ultra‑high‑net‑worth (UHNW) individuals and families. As a senior member of the team, the Director will design and implement advanced tax mitigation strategies that integrate with clients’ broader estate, investment, and philanthropic objectives.

This is a purely advisory position, with no responsibility for client tax return preparation or compliance work. The Director will engage directly with Cresset’s most complex clients, their family offices, external advisors, and internal stakeholders to provide deep technical insights and strategic guidance across a wide range of income tax matters. Areas of focus will include individual, trust, and pass‑through entity taxation;

planning for concentrated stock positions and equity compensation; and structuring family offices and closely held businesses.

Beyond technical expertise, the ideal candidate will bring a collaborative and entrepreneurial mindset, with a passion for building and scaling a best‑in‑class tax strategy offering. This role offers the opportunity to shape the evolution of the team’s capabilities, contribute to thought leadership, and elevate the client experience. The Director will report directly to the Managing Director, Head of Tax Strategy, and will be instrumental in shaping the long‑term vision and growth of the tax practice within a dynamic and fast‑growing organization.

• Conduct in‑depth research and analysis of individual, trust, partnership, and corporate income tax issues relevant to UHNW clients.
• Evaluate clients’ existing entity structures, including family limited partnerships and LLCs, to identify planning opportunities and risks.
• Design and assess advanced income tax planning strategies, philanthropic planning, and planning for concentrated stock positions, incentive benefits, non‑qualified stock options (NQSOs), incentive stock options (ISOs), and restricted stock.
• Build and review complex spreadsheets to model cash flows and income tax consequences of current and proposed planning strategies.
• Independently review planning documents (e.g., deal structures, operating agreements, equity compensation plans) and provide strategic feedback and recommendations.
• Translate complex tax and planning concepts into actionable insights for clients, helping them understand their options and make informed decisions.
• Work closely with internal estate planning attorneys and other specialists to deliver integrated, high‑impact tax strategies.
• Leverage your professional network to raise the profile of Cresset Capital in the UHNW market, particularly among attorneys, accountants, and other centers of influence.

• JD or CPA required
• Additional advanced degrees or certifications preferred (LLM, MS in Tax, CFA, MBA)
• 8+ years of experience at a law firm, accounting firm, or in‑house tax…