CPA/Tax Strategist

The Well
Winter Garden, FL

About the opportunity-

We’re hiring a CPA/Tax Strategist on behalf of our client—a growing wealth management firm based in Winter Garden, FL. This team is forward-thinking, client-focused, and dedicated to serving high-net-worth individuals, business owners, executives, and medical professionals. Their mission: to deliver proactive, integrated financial and tax planning that creates lasting impact through strategy, collaboration, and insight.

This is not a siloed accounting seat—it’s a chance to join a collaborative wealth planning team, contribute ideas, and work closely with advisors and clients on forward-looking tax strategy.


Seeking candidates that self-directed, independent, highly autonomous, entrepreneurial, & proactive.


Core Responsibilities

  1. Prepare and review individual, trust, and business tax returns for high-net-worth clients
  2. Collaborate year-round with wealth advisors to design and execute proactive tax strategies
  3. Research and implement advanced planning strategies, including entity structuring, retirement, charitable, and equity compensation planning
  4. Partner with the planning team on business succession and transition strategies
  5. Participate in client meetings and strategy sessions, translating complex strategies into clear client conversations
  6. Maintain strong command of evolving tax laws and their impact on client portfolios
  7. Build trusted client relationships and contribute to a team-first, collaborative culture


Candidate Profile

  1. CPA license (required)
  2. 3–5 years of tax experience, preferably with HNW individuals and closely held businesses
  3. Strong technical knowledge in tax compliance and planning
  4. Skilled at explaining complex tax strategies in client-friendly terms
  5. Collaborative, growth-minded, and excited to be part of an integrated advisory team
  6. Interest in financial planning and wealth management is a plus


Compensation & Benefits

  1. Base salary $100,000 – $110,000 (depending on experience)

(135k minimum, OTE for year 1)

  1. Revenue share bonus structure for significant upside potential
  2. Professional development support for CE, licensing, and certifications
  3. Values-driven culture where collaboration, respect, and growth are central
  4. Advancement opportunity for career growth within an expanding advisory firm

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