OLarry Bookkeeper Remote · Full time Company website

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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..

About OLarry

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.

About the Role

As a Bookkeeper at OLarry, you will play a central role in our mission to deliver a world-class tax experience. You'll manage day-to-day financial recordkeeping for a portfolio of clients, ensuring their books are accurate, organized, and ready to support seamless tax preparation by our Tax Advisors. You'll work closely with clients directly, high-net-worth individuals with complex financial lives, as well as with our internal team, to make sure nothing falls through the cracks. This role reports to the Bookkeeping Manager.

Responsibilities

• Maintain accurate, up-to-date books for a portfolio of clients, including recording transactions, reconciling accounts, and categorizing expenses
• Reconcile bank, credit card, and investment accounts on a regular cadence
• Prepare monthly, quarterly, and year-end financial statements and reports
• Identify and resolve discrepancies in financial records in a timely manner
• Partner with Tax Advisors to ensure books are tax-ready and support accurate, efficient filing
• Communicate directly with clients to gather documentation, clarify transactions, and answer bookkeeping-related questions
• Maintain organized, audit-ready financial records within OLarry's proprietary platform
• Flag opportunities to improve a client's financial organization or processes
• Stay current on bookkeeping best practices and relevant accounting standards
• Uphold strict confidentiality and data security standards given the sensitive nature of client financial information

Skills & Experience

• 4+ years of bookkeeping experience, ideally in a public accounting or financial services environment
• Proficiency with bookkeeping/accounting software (e.g., QuickBooks Online, Xero); comfort learning proprietary platforms
• Experience supporting high-net-worth individuals
• Strong attention to detail and a commitment to accuracy
• Ability to communicate complex financial concepts in a way that feels both accessible and high-touch
• A high level of EQ, personal drive, and professionalism that adheres to the OLarry Core Pillars
• Ability to manage multiple client relationships and deadlines simultaneously
• Comfort working in a fully remote, fast-paced startup environment

Benefits & Compensation

• Unlimited PTO.
• Stock Options.
• Healthcare Insurance - 100% coverage for the employee, 50% coverage for dependents.
• Generous revenue sharing for all new business development.
• 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.