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Tax Director

Olarry

Olarry

Remote
USD 185k-250k / year + Equity
Posted on Oct 17, 2025

_______________ Tax Director Remote · Full time Company website

As a Tax Director at OLarry, you’ll serve as the lead advisor for high-net-worth individuals and business clients, delivering proactive tax strategies. You’ll oversee client relationships, manage complex tax planning and compliance, and collaborate cross-functionally to elevate the client experience beyond traditional “tax season” expectations.

About _______________

With deep expertise in tax and technology, we're a team driven to change the landscape of tax by making it more accessible and efficient for all involved. Join us! OLarry only hires individuals based in the U.S..

Description

About the Role

At OLarry, you will be at the forefront of shaping the future of tax. Using and helping advise on progressive technology lets tax professionals focus their expertise where it matters: the client. Together, we can craft the future's innovative tax solutions and strategies.

As a Tax Director, you will be instrumental in driving OLarry’s growth by planning, executing, directing, and completing tax projects that provide clients with innovative tax planning, consulting, and compliance expertise. OLarry supports emerging wealth and high-net-worth clients, including entrepreneurs, executives, partnerships, closely held businesses, estates, and trusts. This role reports to the Chief Accounting Officer.

Responsibilities

  • Market, design, and implement tax-planning strategies for clients and manage to budget.
  • Conduct primary and secondary review of, and have ultimate responsibility for, complex income tax returns, including federal and multi-state filings that include the signing of tax returns.
  • Maintain active communication with clients to manage expectations, ensure satisfaction, ensure deadlines, and effectively lead change efforts.
  • Proactively identify opportunities to expand existing client relationships while also sourcing and closing new high-net-worth and business clients as part of OLarry’s business development efforts, including referrals, outbound introductions, and strategic networking.
  • Responsible for managing, developing, training, and mentoring Associates and Managers on tax projects and assessing performance for engagement reviews.
  • Effectively leverage available technology and other resources to maximize technical application to project and hold the engagement team to the same standard.
  • Determine appropriate tax objectives, scope, and methodology and actively participate in decision-making with the client's management to understand the broader impact of current decisions and possible solutions.
  • Evaluate skills and develop your team in client engagement management and technical expertise in individual, trust, partnership, corporate, federal, state, local, and foreign tax returns, estimated payments and extensions, and federal and state tax audits.

Outcomes of Success

You will be measured by your ability to:

  • Proactive client communication and engagement
  • Ability to recruit, retain, and develop OLarry leaders.
  • Recruit and retain 75% of your prior client base within 3 months of your start date

Skills & Experience

  • Bachelor’s or Master’s degree required; Accounting, Finance, Economics, or related degree preferred.
  • At least 8 years of relevant work experience with an accounting firm, with a minimum of 4 years spent in a supervisory or training capacity.
  • Prior experience working with high-net-worth and emerging wealth clients is preferred.
  • Advanced credentials allowing for client representation before the Internal Revenue Service required (i.e. CPA or JD)
  • Strong technical knowledge of complex tax issues.
  • Ability to work effectively independently and get things done under tight deadlines while juggling multiple priorities
  • Proficient use of technology, including MS Excel and Google Suite.
  • A high level of EQ, personal drive, and professionalism that adheres to the OLarry Core Pillars.

Benefits & Compensation

  • Unlimited PTO.
  • Stock Options.
  • Healthcare Insurance - 100% coverage for the employee, 50% coverage for dependents.
  • We are committed to investing in your career by offering continuous training and support, ensuring you acquire new skills and opportunities.

We are committed to creating a diverse and inclusive workplace. We do not discriminate based on race, color, religion, gender, sexual orientation, gender identity, national origin, age, disability, genetic information, marital status, amnesty, or status as a covered veteran in accordance with applicable federal, state, and local laws. We are also committed to complying with the Ban the Box legislation, which prohibits employers from inquiring about an applicant's criminal background history until a conditional job offer has been made.

OLarry Core Pillars

  • Owner Mindset: Think and spend like shareholders. Long‑term, frugal, fully accountable.
  • Customer‑First: Start with the client, validate every idea in the market, let revenue follow.
  • High-Bar Collaboration: Hire people better than ourselves and share knowledge. No silos, just collective brilliance.
  • Grit & Innovation: Push through obstacles and invent better ways—experiment fast, finish strong.
  • Brand Ambassadors: Grow Olarry in every interaction; selling, serving, and building trust.
  • Build‑to‑Last: Make smart, long‑term choices that compound wealth and strengthen the company; never chase quick wins.

Salary

$185,000 - $250,000 per year