Manage recurring client portfolios and perform full-cycle bookkeeping (GL, reconciliations, A/P, A/R, payroll, month-end). Prepare financial statements, review and mentor bookkeeping and offshore teams, resolve accounting issues, and improve processes. Serve as primary client contact and collaborate with managers and controllers to ensure accurate, audit-ready records and exceptional client service.
Position Summary
The Senior Bookkeeper manages a portfolio of clients while serving as a technical resource, reviewer, and mentor for the bookkeeping team. This role balances client service with quality review, ensuring accurate financial reporting, exceptional client experiences, and consistent adherence to Out of the Box Technology's standards.
Senior Bookkeepers work independently while collaborating with peers, leadership, and offshore team members to solve accounting challenges, improve processes, and support team development in a fast-paced, technology-driven environment.
Primary Responsibilities
Client Management
- Manage a recurring portfolio of multiple clients across various industries.
- Serve as the primary point of contact, building trusted client relationships through proactive communication.
- Complete full-cycle bookkeeping, including general ledger maintenance, journal entries, bank and credit card reconciliations, accounts payable, accounts receivable, payroll, and month-end close.
- Prepare accurate financial statements and ensure financial records remain organized and audit-ready.
- Identify accounting issues, resolve discrepancies, and recommend process improvements.
Review & Team Support
- Review work completed by Bookkeepers and offshore team members to ensure accuracy, completeness, and adherence to company standards.
- Provide coaching, guidance, and technical support to team members on accounting questions and complex transactions.
- Support onboarding and ongoing development by reinforcing best practices and department procedures.
- Identify recurring issues and recommend training or workflow improvements.
- Escalate complex accounting matters when appropriate while helping develop practical solutions.
Client Service & Collaboration
- Explain financial statements and accounting concepts clearly to clients.
- Respond to client questions regarding bookkeeping, payroll, reporting, and financial performance.
- Collaborate with Accounting Managers, Controllers, and internal teams to deliver exceptional client service.
- Contribute to process improvements that enhance efficiency, consistency, and scalability across the department.
Key Competencies
- Advanced knowledge of bookkeeping principles, financial reporting, payroll, and reconciliations.
- Strong client relationship management and communication skills.
- Ability to review work, mentor team members, and promote accountability.
- Excellent organization, time management, and attention to detail.
- Strong analytical and problem-solving skills.
- Adaptability in a fast-paced, technology-enabled environment.
- Commitment to continuous improvement and delivering exceptional client service.
Qualifications
Required
- Associate's or Bachelor's degree in Accounting, Finance, or equivalent experience.
- Three or more years of full-cycle bookkeeping or Client Accounting Services (CAS) experience.
- Experience managing multiple client relationships.
- Advanced proficiency with QuickBooks Online; QuickBooks Desktop experience preferred.
- Strong knowledge of financial statement preparation, reconciliations, payroll, sales tax, and month-end close.
- Excellent communication, organizational, and problem-solving skills.
Preferred
- Experience in an outsourced accounting, CAS, or public accounting environment.
- Experience reviewing work and providing coaching or technical support.
- Experience working with offshore teams.
- Franchise or multi-entity accounting experience.
- QuickBooks ProAdvisor certification and experience with Karbon or similar workflow software.
Interested in joining Out of the Box Technology? Please submit your application through this posting. Applications and hiring inquiries are not accepted by phone. Due to application volume, we are unable to provide status updates by telephone
Similar Jobs
Professional Services • Consulting
Manage end-to-end bookkeeping and financial reporting for US-based small and medium businesses. Own client accounts, handle daily transactions, reconciliations, and financial analysis, liaise directly with clients, and use modern accounting platforms. Mentor teams and grow into managerial responsibilities.
Top Skills:
Bill.ComGoogle SheetsGustoExcelQuickbooksSageStripeXero
Professional Services • Consulting
Lead and oversee day-to-day bookkeeping operations including general ledger maintenance, bank and credit card reconciliations, payroll processing, AP/AR review, month-/year-end closes, financial reporting, client communication, and supervising junior bookkeepers to ensure accuracy, compliance, and timely delivery of audit-ready financial records.
Top Skills:
Google WorkspaceExcelMicrosoft WordQuickbooks
.png)
eCommerce • Fintech • Hardware • Payments • Software • Financial Services
Lead Square-wide Trust strategy across Risk and Identity, owning high-stakes Trust bets while coaching senior PMs. Drive product for Identity Verification, Access, Disputes, and Controls; optimize seller experience, risk loss, and ecosystem health. Operate AI-native, engage regulators and partners, and coordinate Product, Engineering, Compliance, Legal, and Operations to deliver Trust and Safety initiatives.
Top Skills:
JumioMl/AiOnfidoPersonaVeriff
What you need to know about the Boston Tech Scene
Boston is a powerhouse for technology innovation thanks to world-class research universities like MIT and Harvard and a robust pipeline of venture capital investment. Host to the first telephone call and one of the first general-purpose computers ever put into use, Boston is now a hub for biotechnology, robotics and artificial intelligence — though it’s also home to several B2B software giants. So it’s no surprise that the city consistently ranks among the greatest startup ecosystems in the world.
Key Facts About Boston Tech
- Number of Tech Workers: 269,000; 9.4% of overall workforce (2024 CompTIA survey)
- Major Tech Employers: Thermo Fisher Scientific, Toast, Klaviyo, HubSpot, DraftKings
- Key Industries: Artificial intelligence, biotechnology, robotics, software, aerospace
- Funding Landscape: $15.7 billion in venture capital funding in 2024 (Pitchbook)
- Notable Investors: Summit Partners, Volition Capital, Bain Capital Ventures, MassVentures, Highland Capital Partners
- Research Centers and Universities: MIT, Harvard University, Boston College, Tufts University, Boston University, Northeastern University, Smithsonian Astrophysical Observatory, National Bureau of Economic Research, Broad Institute, Lowell Center for Space Science & Technology, National Emerging Infectious Diseases Laboratories
