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Head Bookkeeper Jobs in Springfield, MA (NOW HIRING)

Senior Underwriter, Primary Casualty

Hartford, CT ยท On-site

$99K - $117K/yr

Providing or seeking referral counsel with other underwriters, the Unit Head and/or Corporate ... Monitoring and meeting production, marketing and profitability goals for the SUPC's book. * Keeping ...

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Senior Underwriter, Excess Casualty

Hartford, CT ยท On-site

$99K - $117K/yr

Providing or seeking referral counsel with other underwriters, the Unit Head and/or Corporate ... Monitoring and meeting production, marketing and profitability goals for the SUEC's book. * Keeping ...

New

Senior Underwriter, Primary Casualty

Hartford, CT ยท On-site

$99K - $117K/yr

Providing or seeking referral counsel with other underwriters, the Unit Head and/or Corporate ... Monitoring and meeting production, marketing and profitability goals for the SUPC's book. * Keeping ...

New

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 Sep 4, 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 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 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.

Are head bookkeepers still in demand?

Head bookkeepers are still in demand as organizations require experienced professionals to oversee financial record-keeping, ensure accuracy, and manage accounting teams. Strong skills in accounting software and certifications like CPA or CMA can enhance job prospects in this role. The demand is steady across various industries, especially in small to medium-sized businesses and accounting firms.

Do head bookkeepers make good money?

Head bookkeepers typically earn higher salaries than entry-level bookkeepers due to their leadership responsibilities and experience. Their compensation varies based on industry, location, and company size, with many earning a competitive wage that reflects their expertise in accounting software and financial management. Advanced skills and certifications can also influence earning potential.

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:

Infographic showing various Head Bookkeeper job openings in Springfield, MA as of August 2026, with employment types broken down into 78% Full Time, 18% Part Time, 1% Temporary, 2% Contract, and 1% Nights. Highlights an 94% Physical, 2% Hybrid, and 4% Remote job distribution, with an average salary of $50,853 per year, or $24.4 per hour.

Senior Underwriter, Primary Casualty

IFG Companies

Hartford, CT โ€ข On-site

$99K - $117K/yr

Full-time

Medical, Dental, Vision, Life, Retirement, PTO

Posted yesterday

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Job description

POSITION SUMMARY

The Senior Underwriter, Primary Casualty ("SUPC") is responsible for developing, managing and maintaining a profitable book of primary casualty business on behalf of IFG Companies. This experienced underwriter is expected to develop strong relationships with wholesale producers (i.e., agents and brokers) that will result in favorable submission flows and profitable long-term underwriting results. The SUPC will evaluate submissions for new and renewal business, prioritize them and prepare quotes for those acceptable submissions while strictly adhering to IFG Companies' underwriting guidelines and operating within the bounds of the SUPC's Letter of Authority or otherwise referring business for higher levels of approval.

The SUPC should employ IFG Companies' advanced underwriting tools to support the underwriting and quoting process, including its rating matrices, predictive analytics, crime and credit scores and other third-party data to facilitate the risk selection, evaluation, quoting and binding processes using approved forms.

POSITION RESPONSIBILITIES INCLUDING

New Business

  • Meeting and working with producers in assigned territories to ensure high-quality submission opportunities are presented to the SUPC for quoting.
  • Identifying and selecting suitable submissions for quoting, with assistance from IFG Companies' submission prioritization tools that employ predictive analytics, loss history and third-party data to score each submission.
  • Determining appropriate pricing, structure and coverage terms, with assistance from IFG Companies' rating tools and underwriting guidelines as well as appetite guidance with respect to the class of business being considered.
  • Maintaining excellent communication with producers to keep them informed about the IFG Companies' product line offerings.
  • Promoting the IFG Companies' brand.
  • Assisting IFG Companies' marketing efforts generally by providing feedback pertinent to the product line with respect to competitors, products and the overall marketplace.
  • Providing or seeking referral counsel with other underwriters, the Unit Head and/or Corporate Underwriting, to discuss individual risk acceptance or declination, pricing and terms, when appropriate under the circumstances.
  • Monitoring the performance of new business underwritten.
  • Performing other duties, including new underwriter training and mentoring, as required.

Renewal Business

  • Monitoring the performance of the SUPC's business in force to determine what underwriting actions are most appropriate with respect to renewal, pricing, non-renewal or changes in coverage terms.
  • Preparing renewal quotes sufficiently in advance of renewal dates to satisfy producer and retailer needs.
  • Maintaining excellent communication with producers so they know what to expect at renewal, are then less likely to take actions to move the business and are given due notification whenever possible, if non-renewal or changed terms are expected.
  • Being generally familiar with regulatory and contractual considerations as regards contingent renewals or non-renewals to ensure compliance with the respective state regulations and consulting with IFG Companies' Compliance, as needed.
  • Providing or seeking referral counsel with other underwriters, the Unit Head and/or Corporate Underwriting, to discuss individual renewals or non-renewals, pricing and terms, when required or appropriate.

General Underwriting Responsibilities

  • Exhibiting sound judgment and strong technical knowledge of underwriting principles, while applying IFG Companies' underwriting guidelines that apply to the risks being underwritten.
  • Monitoring and meeting production, marketing and profitability goals for the SUPC's book.
  • Keeping informed of industry, competitor and claim trends that may impact the relative and absolute attractiveness of risks being underwritten.
  • Being or becoming a subject matter expert for certain classes of business that are within IFG Companies' underwriting appetite.
  • Regularly traveling to meet with assigned producers to build and maintain strong relationships and ensure their awareness of IFG Companies' product offerings and appetite.
  • Collaborating and assisting other team members on underwriting and marketing matters.
  • Training, coaching and mentoring less experienced underwriters and support staff.

KNOWLEDGE, SKILLS AND ABILITIES

  • Knowledge of commercial primary casualty lines business, classifications, pricing and coverage options with adherence to applicable statutory compliance requirements and corporate guidelines.
  • Ability to manage the SUPC's primary portfolio with appropriate overall limits, attachment points and diversification.
  • General knowledge of the wholesale producer distribution system.
  • Demonstrated ability to analyze data and make well-informed, calculated risk decisions.
  • Strong problem-solving, reasoning and decision-making skills that aid in providing solutions for producers and insureds, while protecting IFG Companies' economic interests.
  • Excellent written and oral communication skills.
  • Excellent analytical and organizational skills, with excellent attention to detail.
  • Ability to plan, organize, prioritize and manage multiple tasks while meeting deadlines.
  • Proven team player, with an energetic personality and strong interpersonal skills.
  • Strong computer skills and an ability to learn to work with proprietary systems.

EDUCATION, EXPERIENCE AND CERTIFICATIONS

  • Required: minimum of 6+ years of commercial primary casualty underwriting experience, combined with sound knowledge of commercial primary casualty underwriting coverages.
  • Required: a bachelor's degree from an accredited U.S. college/university, with a major or coursework in insurance, risk management, economics, actuarial science or related fields.
  • A Plus: CPCU or other relevant insurance-related designations.

PHYSICAL DEMANDS

  • Physical demands are considered to be that of a climate-controlled office environment, with minimal physical exertion.
  • Position is hybrid and requires the ability and willingness to work in an IFG Companies' office at least three (3) days per week.
  • Position requires prolonged sitting, extensive utilization of computers and interactions with others in person and via phone.
  • Position requires the ability and the willingness to travel as required to meet business needs.

SALARY AND BENEFITS

The salary range for this position is $125,000 to $165,000. Additionally, the position may be eligible to earn incentive compensation.

IFG Companies offers competitive compensation and benefits, currently including medical, dental, vision, 401(k), flexible spending, short-term and long-term disability insurance, life insurance, paid parental leave, vacation and other paid time off.

WHY IFG COMPANIES

Founded in 1985, IFG Companies is one of the oldest privately held insurance groups in the United States. It combines a specialty carrier focus with long-term stability and thinking, while promoting a culture of underwriting rigor, collaboration, strategic thinking, superior technology and strong producer partnerships.

EQUAL OPPORTUNITY

 IFG Companies is an equal opportunity employer. All applicants will be considered for employment without attention to race, color, religion, sex, sexual orientation, gender identity, national origin, veteran or disability status or any other protected characteristic under applicable law.