Director, Tax Strategy

Cresset Capital • Chicago, IL

45d • $175,000 - $200,000

About The Position

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.

Requirements

• JD or CPA required
• 8+ years of experience at a law firm, accounting firm, or in-house tax department; wealth management or family office experience strongly preferred.
• Significant experience working with UHNW clients and family offices
• Deep knowledge of personal, trust, partnership, and corporate income tax disciplines
• Expertise in family entities, wealth transfer planning, philanthropic strategies, and executive compensation planning
• Strong modeling skills using Excel or similar tools to analyze tax and cash flow implications
• Skilled at working with a high degree of autonomy, setting priorities, and managing deadlines
• Strong project coordination and organizational skills
• Collaborative team player with excellent interpersonal and communication skills
• Enthusiastic, polished, poised, and professional demeanor
• Self-motivated and proactive, with a passion for delivering exceptional client service

Nice To Haves

• Additional advanced degrees or certifications preferred (LLM, MS in Tax, CFA, MBA)

Responsibilities

• 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.

Benefits

• Cresset offers a competitive compensation package including an annual incentive and a benefits package to all full-time employees including medical, dental, vision, life insurance, 401(k) retirement plan, health savings accounts, short and long-term disability insurance, voluntary critical and accident insurance, and pre-tax parking and transportation programs.
• Aligning employee and organizational interests, all employees receive equity in Cresset.

What This Job Offers

• Job Type: Full-time
• Career Level: Director
• Education Level: Ph.D. or professional degree
• Number of Employees: 501-1,000 employees