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Head Bookkeeper Jobs in Springfield, MA (NOW HIRING)

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Head Bookkeeper information

See Springfield, MA salary details

$31.4K

$52.1K

$77.7K

How much do head bookkeeper jobs pay per year?

As of Aug 15, 2026, the average yearly pay for head bookkeeper in Springfield, MA is $52,067.00, according to ZipRecruiter salary data. Most workers in this role earn between $37,900.00 and $66,300.00 per year, depending on experience, location, and employer.

What are the key skills and qualifications needed to thrive as a head bookkeeper, and why are they important?

To thrive as a Head Bookkeeper, you need strong accounting knowledge, attention to detail, and experience with financial reporting, typically supported by an associate's or bachelor's degree in accounting or finance. Proficiency in accounting software such as QuickBooks, Xero, or Sage, as well as familiarity with spreadsheets and payroll systems, is essential. Excellent organizational skills, integrity, and effective communication distinguish top performers in this role. These skills ensure accurate financial records, regulatory compliance, and smooth collaboration with management and external stakeholders.

What are some common challenges faced by a head bookkeeper, and how can they be addressed?

A Head Bookkeeper often manages complex accounts, oversees junior staff, and ensures compliance with financial regulations, which can be challenging when balancing tight deadlines and high accuracy standards. Effective time management, strong organizational skills, and staying updated on the latest accounting software and regulations are key to overcoming these hurdles. Additionally, clear communication with team members and regular training can help ensure consistency and accuracy across all bookkeeping tasks.

What is the difference between Head Bookkeeper vs Bookkeeper?

AspectHead BookkeeperBookkeeper
CertificationsTypically requires certifications like QuickBooks Certified User or bookkeeping coursesOften requires basic bookkeeping certifications or none
Work EnvironmentSupervises bookkeeping staff, manages accounting processesPerforms day-to-day transaction recording
ResponsibilitiesOversees financial records, ensures accuracy, manages teamMaintains ledgers, processes invoices and payments
Industry UsageCommon in larger organizations or accounting firmsFound in small to medium businesses

The Head Bookkeeper typically has more managerial responsibilities and oversees the bookkeeping team, while a Bookkeeper focuses on daily transaction recording. Certifications and work environment overlap, but the Head Bookkeeper plays a supervisory role in larger organizations.

What is a head bookkeeper?

Head Bookkeepers are senior accounting professionals responsible for overseeing and managing the financial records of an organization. They supervise bookkeeping staff, ensure the accuracy of ledgers and financial statements, and often handle payroll, reconciliations, and regulatory compliance. Head Bookkeepers play a crucial role in maintaining the integrity of financial data and providing reports that support business decision-making. They typically report to financial managers or business owners and may help implement accounting policies and procedures.

What are the most commonly searched types of Bookkeeper jobs in Springfield, MA?

The most popular types of Bookkeeper jobs in Springfield, MA are:

What cities near Springfield, MA are hiring for Head Bookkeeper jobs?

Cities near Springfield, MA with the most Head Bookkeeper job openings:

Head Bookkeeper jobs near you
Infographic showing various Head Bookkeeper job openings in Springfield, MA as of August 2026, with employment types broken down into 1% As Needed, 75% Full Time, 21% Part Time, 1% Temporary, 1% Contract, and 1% Nights. Highlights an 93% Physical, 2% Hybrid, and 5% Remote job distribution, with an average salary of $52,067 per year, or $25 per hour.

Finance Manager

New England Jewish Academy

West Hartford, CT • On-site

Full-time

PTO

Posted yesterday

New

Job description

Finance Manager
New England Jewish Academy
West Hartford, CT

New England Jewish Academy, an ECC-12th-grade school in West Hartford, CT, is seeking a full-time Finance Manager—a key leadership position reporting directly to the Head of School. We are a small school with a budget of ~$3MM, passionate about making a meaningful difference in the lives of our students and our community.

Position Overview

The Finance Manager plays a central role in ensuring the smooth financial functioning of the school. This position is responsible for managing financial systems, overseeing daily operations, and supporting the school’s mission to empower students with the academic, character, and life skills they need to thrive.

Key Responsibilities

  • Financial Management:

    • Bookkeeping, including tracking payments, expenses, and reconciling accounts.

    • Creating, monitoring, and tracking the annual budget and cash flow.

    • Collecting tuition and other payments via FACTS and a variety of other platforms.

    • Creating tuition contracts in conjunction with the tuition committee. 

    • Collaborating with external accountants for the annual audit and ensuring compliance with financial regulations.

    • Overseeing school-wide purchasing.

    • Making deposits and ensuring timely bill payments. 

    • Obtaining grant payments upon completion of grant terms; completing necessary paperwork.

    • Tracking and acknowledging all donations via DonorPerfect.

  • Human Resources and Employee Support:

    • Onboarding new employees, including running background checks and managing employment documentation.

    • Assisting in maintaining a supportive and compliant HR environment.

    • Overseeing payroll, including managing PTO and teacher attendance via Paylocity.

Qualifications

  • Prior experience in finance or a related field, preferably in an educational or nonprofit setting.

  • Proficient with technology.

  • Knowledge of best practices in financial management.

  • Proficiency in utilizing and analyzing data for decision-making.

  • Strong organizational skills with an ability to manage multiple priorities effectively.

  • Excellent interpersonal and communication skills, with the ability to engage proactively and respectfully with a broad range of stakeholders.

  • Commitment to collaboration and fostering a positive team environment.

  • Dedication to the school’s mission and values, with a determination to contribute to its growth and success.

  • Experience with school financial systems or familiarity with tuition management platforms preferred.

Why Join New England Jewish Academy?

We are a vibrant, mission-driven school dedicated to creating a nurturing environment where students excel academically, develop strong character, and are prepared for lifelong learning. Joining our team means becoming part of a collaborative community that values integrity, purpose, and growth.

To Apply:
Please send a cover letter and resume to positions@neja.org.

Salary commensurate with experience.