Director of Tax & Family Office Strategy

Location: Chicago, IL Company: Skybox Capital Compensation: $160,000–$190,000 base + target bonus Experience: 7–15+ years CPA: Strongly preferred About Skybox Capital Skybox Capital is a Chicago-based family office and investment platform with interests across operating companies, private investments, real estate, and other investment vehicles. As the organization and its portfolio continue to grow, we are looking for a Director of Tax & Family Office Strategy to take ownership of the family's broader tax agenda and coordinate the sophisticated network of outside professionals supporting it. This is not a traditional corporate tax compliance role. The Director will serve as the internal quarterback across Skybox's entities, operating businesses, investments, trusts, and family-office structures—ensuring outside tax, legal, accounting, and specialty advisers are working together effectively and that opportunities are identified, evaluated, and implemented. The Role The Director of Tax & Family Office Strategy will become the internal owner of Skybox's tax landscape. You will develop a deep understanding of the family's entities, trusts, operating companies, investment structures, and tax obligations and serve as the primary internal point of coordination with outside tax advisers, attorneys, accountants, and specialty consultants. You are not expected to personally solve every highly technical tax question or prepare every return. Instead, you will know enough to recognize potential issues and opportunities, bring in the right specialists, ask the right questions, and drive projects through implementation. The goal is simple: make sure Skybox's tax advisers are consistently working together in Skybox's best interest and that valuable planning opportunities do not fall through the cracks. Key Responsibilities Own and coordinate the overall tax agenda across the family office, operating companies, investments, trusts, partnerships, and other entities.Serve as the primary internal liaison with outside tax advisers, attorneys, accounting firms, wealth advisers, and specialty tax professionals.Develop a comprehensive understanding of the family's legal and tax structure and maintain accurate entity, ownership, and organizational records.Maintain a master tax calendar covering filings, estimates, elections, planning deadlines, transactions, and other key dates.Coordinate the collection and organization of information required by outside advisers, reducing unnecessary professional-service costs and improving execution.Manage federal, state, individual, partnership, trust, estate, gift, and other tax workstreams in partnership with external specialists.Review tax returns, projections, analyses, and recommendations at a strategic level and ensure appropriate internal and external parties are aligned.Proactively identify areas requiring additional analysis or specialist involvement, including SALT, international tax, estate and gift planning, transaction structuring, cost segregation, credits, and other specialty areas.Coordinate quarterly and year-end tax strategy discussions with external advisers.Prepare agendas, questions, supporting materials, and follow-up items for tax and estate-planning meetings.Challenge outside advisers to proactively evaluate opportunities, alternatives, and potential risks rather than simply completing required filings.Coordinate tax planning related to acquisitions, dispositions, new investments, operating businesses, real estate, charitable giving, and other significant transactions.Request and coordinate modeling and scenario analysis when evaluating potential structures or planning strategies.Obtain second opinions or engage additional specialists when appropriate.Translate complex tax recommendations into understandable business implications for family members and internal leadership.Establish clear ownership for recommendations and ensure approved strategies are actually implemented.Continuously evaluate the family office's structure for tax efficiency, administrative efficiency, risk, and long-term planning opportunities. What We're Looking For 7–12+ years of relevant tax, private-client, or family-office experience.CPA strongly preferred.Experience working with high-net-worth or ultra-high-net-worth individuals, families, family offices, or closely held business owners.Strong knowledge of individual taxation and partnerships/pass-through entities.Meaningful exposure to trusts, estates, gifting, wealth-transfer planning, and closely held operating businesses.Broad enough tax knowledge to recognize when specialized expertise is required across areas such as SALT, international tax, estate planning, and transactions.Experience coordinating multiple advisers, entities, workstreams, and deadlines for sophisticated clients.Ability to review and understand complex tax structures without needing to personally perform every technical analysis.Strong project-management and organizational skills.Commercial mindset with the ability to understand how tax decisions interact with investments, operating companies, liquidity, and broader family-office objectives.Strong communication skills and the confidence to challenge sophisticated external advisers when appropriate.High level of discretion when handling confidential financial, tax, investment, and family information. What Success Looks Like Within the first year, the Director will have a comprehensive understanding of Skybox's entities and tax structure, a centralized calendar and process for managing tax obligations, clear visibility into all active planning initiatives, and strong working relationships with the family's outside advisers. Most importantly, Skybox will have one internal person responsible for continuously asking: What are we missing? What should we be doing before year-end? What happens if we structure this differently? Has this been modeled? Who owns the next step? And has the recommendation actually been implemented? The Director of Tax & Family Office Strategy will make sure those questions are consistently answered—and acted upon. The successful candidate will be a broad, commercially minded tax professional who understands sophisticated tax issues but is equally strong at coordination, prioritization, project management, and execution.