Senior Field Business Development Representative

Plymouth Rock Assurance•Boston, MA

16h•$94,000 - $127,500

About The Position

The Senior Field Business Development Representative is responsible for the strategic oversight, growth, and performance management of a defined group of independent agents within Massachusetts. This role serves as a senior relationship owner, driving profitable growth, optimizing agency performance, and aligning field execution with the Company’s long-term strategic objectives. The Senior Representative acts as a trusted advisor to top-tier agency partners and a key liaison between field operations and internal leadership, ensuring alignment across underwriting, marketing, service, and product teams.

Requirements

5+ years of Field Sales/Marketing experience working with Independent Agents required, with a demonstrated track record of high performance.
Bachelor’s degree required; advanced industry experience (7+ years) may be considered in lieu of degree.
Strong Personal Lines product expertise required.
Demonstrated ability to operate at both strategic and tactical levels.
Exceptional analytical, communication, and presentation skills, with experience engaging senior stakeholders.
Proven leadership capabilities, including influencing without authority and mentoring others.
Must reside in Massachusetts.
Valid driver’s license and favorable driving record required.

Nice To Haves

Professional designations such as CIC or CPCU strongly preferred.

Responsibilities

Accountable for developing and executing strategic production plans for each agency, aligned with enterprise growth and profitability objectives.
Lead the analysis, forecasting, and performance management of agency production, proactively identifying trends, risks, and opportunities; adjust strategies to ensure achievement of territory goals.
Drive territory-level strategy, including segmentation of agencies, prioritization of high-value partners, and optimization of resource allocation.
Develop, implement, and evaluate advanced sales programs and initiatives, ensuring measurable impact and scalability across the territory.
Serve as a senior advisor to agency leadership, providing consultative guidance on book management, growth strategies, and market positioning.
Conduct in-depth portfolio and profitability analysis of each agency’s book of business; design and execute targeted action plans to improve performance.
Establish and oversee robust follow-up and accountability frameworks to ensure sustained execution and results.
Lead and present comprehensive territory and executive-level reviews, delivering insights and strategic recommendations to internal stakeholders.
Translate and communicate target market strategy, including preferred risk profiles and acquisition channels, ensuring alignment with underwriting and product strategy.
Identify systemic service or operational issues, lead cross-functional resolution efforts, and drive continuous improvement initiatives.
Maintain a high-impact agency visitation strategy, prioritizing strategic engagements over transactional interactions.
Act as a subject matter expert on company products, underwriting guidelines, and market positioning; deliver advanced training and mentorship to agency partners.
Maintain deep expertise in Massachusetts auto and home insurance regulations and ensure agency compliance and best practices.
Monitor and analyze competitive intelligence and market trends, translating insights into actionable strategies for both field and internal teams.
Lead agency appointment strategy, including identifying, recruiting, and evaluating high-potential agency partners aligned with long-term company goals.
Conduct thorough due diligence and business case development for prospective agency appointments.
Demonstrate advanced sales and negotiation expertise, including the ability to influence, close, and expand complex agency relationships.
Mentor and support junior team members, sharing best practices and contributing to overall team capability development.