Bookkeeper

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