Advanced Tax Strategist (Tampa)

Questmont Virtual Family Office is a boutique wealth management and family office firm serving high- and ultra-high-net-worth families, business owners, and entrepreneurs.

Our mission is to guide and protect the families we serve. We take extreme ownership of our clients’ financial lives, helping them navigate complexity, preserve what they have built, and make thoughtful decisions for their businesses, families, and legacies.

We are not a traditional hierarchical firm where success is defined by climbing a corporate ladder. Every member of our team plays a meaningful role in the client experience. We are looking for someone who wants to grow—with our clients, our team, and the firm.

The Opportunity

Questmont is seeking an experienced Advanced Tax Strategist to identify, evaluate, and help implement sophisticated tax-planning opportunities for high- and ultra-high-net-worth clients.

This is a strategic planning role—not a tax-return preparation or compliance position. The Advanced Tax Strategist will review and analyze individual, corporate, partnership, and trust tax returns to uncover opportunities, identify risks, and develop proactive tax-mitigation strategies.

You will work alongside our advisors and clients’ existing CPAs, attorneys, and other professionals to ensure tax planning is integrated into the family’s broader financial, business, estate, and legacy objectives.

What You Will Do

• Review and analyze individual, corporate, partnership, and trust tax returns.
• Identify tax-planning and mitigation opportunities for high- and ultra-high-net-worth families and closely held business owners.
• Develop proactive, multi-year tax strategies—not simply year-end recommendations.
• Model the potential financial and tax impact of planning alternatives.
• Support business owners before, during, and after a sale, recapitalization, or other liquidity event.
• Evaluate strategies involving business entities, executive compensation, charitable planning, estate planning, investments, real estate, and wealth transfer.
• Research and vet new or emerging tax strategies to determine their technical validity, economic value, implementation requirements, risks, and suitability for Questmont clients.
• Monitor changes in federal and state tax laws and translate those developments into actionable planning opportunities.
• Collaborate with financial advisors, CPAs, estate-planning attorneys, insurance professionals, and other members of a client’s advisory team.
• Present complex tax concepts to clients and colleagues in a clear, practical, and understandable way.
• Assist in developing internal planning processes, technical resources, and client education materials.
• Maintain complete, organized documentation of planning recommendations, assumptions, risks, and required follow-up.
• Help protect clients from strategies that are overly aggressive, poorly structured, or inconsistent with their broader goals.

What We Are Looking For

• Significant experience working with high-net-worth or ultra-high-net-worth individuals, families, and business owners.
• Strong ability to read and analyze complex individual, corporate, partnership, and trust tax returns.
• Deep understanding of advanced income-tax planning, entity taxation, business-owner planning, estate and trust taxation, charitable planning, and liquidity-event planning.
• Ability to distinguish between a technically possible strategy and one that is genuinely appropriate for the client.
• Strong research, analytical, modeling, and critical-thinking skills.
• The judgment and confidence to challenge assumptions, ask difficult questions, and identify potential risks.
• Ability to communicate sophisticated tax concepts without unnecessary jargon.
• A collaborative mindset and respect for the roles of outside CPAs, attorneys, and other advisors.
• High standards of discretion, integrity, accuracy, and professional accountability.
• A proactive, intellectually curious approach to planning.

Education and Experience

• Bachelor’s degree in accounting, taxation, finance, or a related field required.
• CPA, JD, LLM in Taxation, or other advanced tax credential strongly preferred.
• Five or more years of relevant tax-planning or advisory experience preferred.
• Experience with closely held businesses, trusts, complex ownership structures, and significant liquidity events is highly valued.
• Tax-return preparation experience is helpful, but this role is focused on planning, analysis, and strategy—not production-based return preparation.

The Person Who Will Thrive Here

You are technically strong, but you understand that expertise alone is not enough. You care about the people behind the numbers and take seriously the responsibility that comes with advising families on consequential financial decisions.

You are naturally curious. You do not accept a strategy simply because it is popular, profitable, or technically permissible. You investigate how it works, where it can fail, who should—and should not—consider it, and how it fits into the client’s broader financial life.

You are comfortable working within a boutique environment where every team member contributes, takes ownership, and remains close to the client. You do not need layers of hierarchy or a title-driven career path to feel successful.

You want to grow—not climb.

You want to deepen your expertise, expand your impact, help build something exceptional, and become an indispensable member of a team committed to guiding and protecting the families it serves.

Why Questmont

• Meaningful work with sophisticated families and business owners.
• A planning-first environment focused on advice rather than product sales.
• The opportunity to evaluate and apply advanced strategies across tax, estate, investment, charitable, and business planning.
• Direct collaboration with experienced advisors and outside professionals.
• A boutique culture where your expertise, judgment, and ideas matter.
• The opportunity to help shape the firm’s advanced tax-planning capabilities as Questmont continues to grow.