Out of the Box

    The Bookkeeping Manager I (Executive Director I) at Out of the Box Technology is a senior leadership role responsible for overseeing a team of bookkeepers, ensuring consistent excellence in financial service delivery, and driving operational improvements across client accounts. This role combines expert-level bookkeeping knowledge, team leadership, and process management to optimize performance and client satisfaction.

    As a key member of the accounting leadership team, the Bookkeeping Manager I collaborates with Executive Directors, Directors, and other stakeholders to ensure accurate financial operations, deliver high-impact client solutions, and support the development and retention of high-performing team members.

    Primary Responsibilities

    • Lead and manage a team of bookkeepers, providing oversight, guidance, and performance feedback.
    • Ensure the accuracy and consistency of bookkeeping deliverables across client accounts.
    • Oversee capacity planning, workload balancing, and quality assurance across team members.
    • Coach team members on best practices, technical skills, and client communication.
    • Support client retention by ensuring timely delivery of services and addressing client concerns.
    • Provide technical expertise and support on complex client issues, escalations, and financial discrepancies.
    • Partner with senior leadership to improve internal processes and implement standard operating procedures (SOPs).
    • Monitor key performance indicators (KPIs) to ensure team productivity and service excellence.
    • Participate in recruitment, onboarding, and training of new bookkeepers.
    • Collaborate cross-functionally with other departments to drive firm-wide improvements and service alignment.

    Bookkeeping Oversight and Quality Control

    • Review financial reports and reconciliations prepared by team members to ensure accuracy and compliance.
    • Provide final approval on complex account reconciliations, journal entries, and reporting packages.
    • Ensure consistency in chart of accounts, classifications, and general ledger maintenance across clients.
    • Monitor timelines for monthly close processes and ensure timely deliverables.
    • Provide technical support for QuickBooks Online (QBO) and QuickBooks Desktop (QBD) configurations and workflows.

    Client and Team Communication

    • Serve as the primary escalation point for complex client issues or team challenges.
    • Maintain a proactive communication rhythm with clients and internal teams.
    • Support client onboarding and transitions, ensuring smooth handoffs and successful launches.
    • Provide regular feedback and coaching to team members through one-on-ones and team meetings.

    Operational and Strategic Support

    • Lead initiatives for service delivery optimization, automation, and workflow standardization.
    • Identify training needs and facilitate professional development for team members.
    • Track team KPIs, billing hours, and client margin performance.
    • Assist with strategic planning, departmental goal setting, and budgeting input.
    • Stay updated on regulatory and industry changes affecting bookkeeping operations.

    Competencies

    • Leadership and Team Development – Builds strong, capable teams through mentorship, accountability, and support.
    • Operational Excellence – Focused on quality, accuracy, and consistency in service delivery.
    • Client-Centric Approach – Committed to delivering exceptional client experiences through proactive service.
    • Strategic Thinking – Applies a big-picture mindset to support business goals and drive improvements.
    • Process Optimization – Continuously identifies areas for improvement and efficiency gains.
    • Communication and Collaboration – Leads with transparency, clarity, and a spirit of partnership.
    • Technical Proficiency – Deep expertise in bookkeeping operations and QuickBooks tools.

    Qualifications

    • Bachelor’s degree in Accounting, Finance, Business, or equivalent experience.
    • CPA preferred.
    • 7+ years of bookkeeping or accounting experience, including 3+ years in a team leadership role.
    • Expert-level knowledge of QuickBooks Online and QuickBooks Desktop.
    • Experience in managing people, systems, and processes in a multi-client service environment.
    • Strong understanding of financial compliance, reporting, and operational efficiency.

    How to Advance to Bookkeeping Manager II (Executive Director II)

    Potential next steps in career progression:

    • Demonstrate consistent excellence in team leadership, service delivery, and client satisfaction.
    • Drive significant improvements in departmental performance, KPIs, and workflow efficiency.
    • Take ownership of larger strategic initiatives such as firm-wide process improvement, technology implementations, or training programs.
    • Successfully lead complex projects involving cross-functional collaboration and long-term planning.
    • Mentor and develop emerging leaders within the bookkeeping team.
    • Exhibit strategic thinking and decision-making that supports broader business goals and organizational growth.
    • Consistently model high-level communication, collaboration, and operational excellence.

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