OLarry Tax Director Remote · Full time Company website

Use your tax skills to craft the next generation of Tax practice.


About Us

OLarry is shaping the future of tax by bringing together tax experts and technology leaders to create a tax practice that provides exceptional service supported by leading proprietary technology.  We want to help HENRY’s and beyond build better relationships with their accountants to guide wealth across generations. 

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. 


  • 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. 
  • 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

  • Salary Range: 165k – 250k. Actual salary based on qualifications and experience.
  • Unlimited PTO.
  • Stock Options.
  • Healthcare Insurance - 100% coverage for the employee, 50% coverage for dependents. 
  • Generous revenue sharing for all new business development. 
  • Up to 10% sign-on bonus relative to the book of business brought to OLarry – contingent on signed engagement letters w/ OLarry within 3 months of employment.
  • 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

  • Personal Ownership: All team members of both the company and acquired CPAs will own a stake in the company. With this equity, an expectation of acting as an owner of their given area is expected.
  • Demonstrate Grit: All successful new ventures take time and determination. Team members are expected to be personally driven to succeed on the schedule required by the work and to put their short-term financial needs behind the company's long-term needs. 
  • Collaboration Before Siloed Heros: The strongest products are built by many minds with many viewpoints, not individuals. All team members must hold themselves to a high level of communication and cross-collaboration. No projects or products should be produced in a silo. 
  • Work Backwards: Everything we do puts the customer at the heart. If the customer is happy, the revenue will come. 
  • Market Validation: All products and processes should be tested and validated with the target customer before any major commitment to the project commences. All team members are responsible for talking to customers and understanding their needs. 
  • Area Expertise: Each team member will be the given expert in their allotted part of any project, and knowledge will be deferred to as such. 
  • Build the Brand: Every team member will be responsible for building the OLarry brand through social, sales, or customer support.  
  • Long-term View with a Global Focus: Strategic decisions will be made with a company's first view for building long-term wealth globally before short-term personal gains or expenses. 
  • Think Bootstrapped, not Funded: Team members will treat OLarry’s cash like their own, being careful only to spend it when a valid business case is presented and no market short—or long-term alternative is available.


$165,000 - $250,000 per year