Senior Field Business Development Representative

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.

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.

Qualifications

• 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.
• Professional designations such as CIC or CPCU strongly preferred.
• 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.

Perks and Benefits:

• 4 weeks accrued paid time off + 9 paid national holidays per year
• Free onsite gym at our Boston Location
• Tuition Reimbursement
• Low cost and excellent coverage health insurance options that start on Day 1 (medical, dental, vision)
• Robust health and wellness program and fitness reimbursements
• Auto and home insurance discounts
• Matching gift opportunities
• Annual 401(k) Employer Contribution (up to 7.5% of your base salary)
• Various Paid Family leave options including Paid Parental Leave
• Resources to promote Professional Development (LinkedIn Learning and licensure assistance)
• Convenient location directly across from South Station and Pre-Tax Commuter Benefits

The pay range for this position is $94,000- $127,500 annually. Actual compensation will vary based on multiple factors, including employee knowledge and experience, role scope, business needs, geographical location, and internal equity.

About the Company

The Plymouth Rock Company and its affiliated group of companies write and manage over $2 billion in personal and commercial auto and homeowner's insurance throughout the Northeast and mid-Atlantic, where we have built an unparalleled reputation for service. We continuously invest in technology, our employees thrive in our empowering environment, and our customers are among the most loyal in the industry. The Plymouth Rock group of companies employs more than 1,900 people and is headquartered in Boston, Massachusetts. Plymouth Rock Assurance Corporation holds an A.M. Best rating of "A-/Excellent".