Employment Opportunities
Life as a Pioneer!
Pioneer Insurance is built on the mantra, "Where traditional service meets modern convenience." To uphold this commitment, we strive to put together a team that is positive, responsive, and mission driven. Building trust and providing peace of mind are central to our role as a community insurance provider, and how we succeed and grow as a business.
At Pioneer Insurance, we value, appreciate, and support our employees along with all they bring to the table. We believe in creating a positive work environment, fostering individual development, and maintaining an open forum for discussion, encouraging ideas and innovation. Whether you're a well-established seasoned professional or just starting out in the business, we have a place for you!
Open opportunities at Pioneer Insurance are listed below. You can also connect with us anytime on LinkedIn.
Open Positions
Competitive Compensation: Commissions paid on self-produced new business!
Position Description
This is a full-time role for a Commercial Lines Account Manager located on-site in Yarmouth Port, MA. The Commercial Lines Account Manager will be responsible for managing client accounts, providing exceptional customer service, and advising clients on commercial lines coverages. The role includes handling daily inquiries, writing new policies, renewing policies, and claims assistance. You will work closely with clients and insurance carriers to ensure efficient service and customer satisfaction.
Qualifications
- Expertise in Commercial Lines Coverage
- Basic Personal Lines knowledge a plus
- Strong Account Management and Customer Service skills
- Ability to work well with team members
- Comfortable referring clients between lines of business
- Proven track record of high retention ratios
- Ability to write, produce, and refer new business
- Excellent communication and interpersonal skills
- Ability to work independently and manage multiple tasks simultaneously
- Proficiency in insurance agency management software (Applied EPIC preferred)
- Minimum 3 years of commercial lines experience preferred
- Property & Casualty, Life and Health licenses preferred
Job Category: Commercial Lines Account Manager
Job Type: Full Time
Job Location: Yarmouth Port
Competitive Compensation: Commissions paid on self-produced new business!
Position Description
This is a full-time role for a Personal Lines Account Manager located on-site in Yarmouth Port, MA. The Personal Lines Account Manager will be responsible for managing client accounts, providing exceptional customer service, and advising clients on personal lines coverages. The role includes handling daily inquiries, writing new policies, renewing policies, and claims assistance. You will work closely with clients and insurance carriers to ensure efficient service and customer satisfaction.
Qualifications
- Experience in Account Management and Customer Service
- Expertise in Personal Insurance Coverage
- Basic Commercial Insurance knowledge a plus
- Ability to work well within a team environment
- Proven track record of high retention ratios
- Comfortable referring clients between lines of business
- Strong communication, interpersonal, and negotiation skills
- Excellent organizational and time-management skills
- Ability to work independently and manage multiple tasks simultaneously
- Ability to write, produce, and refer new business
- Proficiency in insurance agency management software (Applied EPIC preferred)
- Minimum 3 years of personal lines experience preferred
- Property & Casualty, Life and Health licenses preferred
Job Category: Personal Lines Account Manager
Job Type: Full Time
Job Location: Yarmouth Port
Position Overview
The Employee Benefits Producer/Manager is responsible for generating new business, managing existing client relationships, and overseeing the delivery of high quality benefits solutions across the team. This role combines sales, consulting, and operational leadership to ensure clients receive strategic guidance, compliant plan administration, and exceptional service, while also developing and leading a team of producers and account managers.
Business Development & Sales
- Prospect, identify, and secure new employee benefits clients through networking, referrals, and targeted outreach
- Conduct needs assessments and present tailored benefits solutions (medical, dental, vision, life, disability, voluntary benefits, etc.)
- Prepare and deliver proposals, renewal presentations, and strategic benefits recommendations
- Maintain a strong pipeline and meet to or exceed production goals
- Manage and support the sales team to ensure goals are being met
- Work with account managers on their development, goals, etc
Client Management
- Serve as the primary point of contact for benefits related accounts
- Manage renewals, marketing, and carrier negotiations to ensure competitive pricing and plan design
- Provide ongoing consultation regarding plan performance, cost containment, compliance, and employee engagement
- Coordinate enrollment meetings, employee communications, and benefit education sessions
- Resolve client issues promptly, including claims concerns, billing discrepancies, and eligibility questions
Compliance & Administration
- Ensure client plans comply with federal and state regulations (ACA, ERISA, COBRA, HIPAA, Section 125, etc.)
- Assist clients with required documentation such as SBCs, 5500 filings, and plan summaries
- Maintain accurate records, documentation, and client files within agency management systems
- Stay current on regulatory changes and communicate impacts to clients
- Act as our HIPAA Compliance Team Leader
Carrier & Vendor Coordination
- Build and maintain strong relationships with carriers, TPAs, and vendor partners
- Oversee quoting, underwriting, and plan implementation processes
- Evaluate and recommend technology tools, HRIS platforms, and enrollment systems
Internal Leadership & Collaboration
- Work closely with agency leadership to develop growth strategies and product offerings
- Mentor and support benefits producers, account managers, and service staff
- Promote and utilize cross selling opportunities with commercial and personal lines teams
Qualifications
- Active Life & Health (required) & Property Casualty license (preferred)
- CEBS Designation or similar preferred
- 4–5+ years of employee benefits experience in an agency, brokerage, or carrier environment
- Strong knowledge of group health plans, ancillary benefits, and compliance requirements
- Proven sales ability with a track record of meeting production goals
- Excellent communication, presentation, and relationship building skills
- Strong organizational skills and attention to detail
- Proficiency with benefits technology platforms and agency management systems
Working Conditions
- A hybrid in-office/work from home position is open for discussion
- 40-hour work week
- Company outings, casual Friday’s, vacation days, personal days, sick days
- Travel to client locations, carrier meetings, networking events, and industry events as needed
Compensation
- Commensurate base salary for management duties
- Generous commission structure for new business produced and referred
- Renewal commissions will be paid
- Bonus potential for team(s) meeting/exceeding goals
- Benefits package will be available
This role is ideal for a driven professional who can balance sales growth with exceptional client service and managing a team. The Employee Benefits Producer/Manager plays a critical role in expanding the agency’s benefits division while ensuring clients receive expert guidance and compliant, cost effective plans.
Job Category: Employee Benefits Producer - Division Manager
Job Type: Full Time
Job Location: Yarmouth Port
