Director of Sales

Director of Sales

Plymouth Rock Assurance is seeking an innovative, results-driven sales leader to help shape the future of our Direct Response and Brokerage Sales organization.

This role leads a complex, multi-state sales operation that includes inbound and outbound sales, brokerage distribution, customer onboarding, sales operations, workforce management, training, and sales enablement. The organization supports multiple personal lines products, including Auto, Property, Umbrella, Motorcycle, and other emerging insurance solutions across Plymouth Rock's growing footprint.

A key differentiator of this role is leadership of Plymouth Rock's unique customer-first distribution model, which combines direct sales capabilities with a growing network of carrier partners to deliver the best possible solution for customers while maximizing growth opportunities.

The Director of Sales will play a critical role in driving the next phase of growth for Plymouth Rock's Direct and Brokerage channels. This leader will be responsible for unlocking breakthrough performance across sales, customer experience, onboarding, retention, operational excellence, and digital engagement while helping shape the future of how customers interact with Plymouth Rock.

This highly visible leadership position reports to the Vice President of Service, Underwriting & Sales and partners closely with executive leadership across Service, Product, Underwriting, Marketing, Technology, and Digital Experience. Success in this role will be measured not only by sales and growth results, but also by the ability to develop talent, strengthen leadership capability, improve customer outcomes, and position the organization for its next stage of growth.

Responsibilities

Lead a High-Performing Sales Organization

• Provide strategic leadership for Plymouth Rock's inbound and outbound sales operations, brokerage sales organization, onboarding functions, and sales support teams.
• Lead a multi-state, multi-product sales organization supporting Auto, Property, Umbrella, Motorcycle, and other personal lines products.
• Drive profitable growth while balancing customer experience, operational efficiency, and business performance objectives.
• Build a culture of accountability, innovation, collaboration, and continuous improvement.
• Develop high-performing leaders and strengthen organizational bench depth through coaching, talent development, and a culture of accountability, continuous learning, and growth.

Drive Growth and Breakthrough Performance

• Own key sales and operational metrics, including conversion, productivity, close rate, staffing efficiency, customer satisfaction, retention impact, and acquisition economics.
• Identify and execute transformational opportunities that improve sales effectiveness, customer experience, operational efficiency, and overall business performance.
• Challenge the status quo and drive breakthrough improvements in conversion, productivity, customer satisfaction, employee engagement, and growth.
• Lead forecasting, budgeting, workforce planning, and expense management for the sales organization.
• Partner closely with Marketing to align lead generation, campaign strategy, staffing, and conversion objectives.

Drive Customer Experience & Digital Transformation

• Lead initiatives focused on customer experience, onboarding optimization, retention, and customer lifetime value.
• Continuously evaluate the customer journey to identify friction points, operational inefficiencies, and opportunities to improve customer outcomes.
• Partner closely with Technology, Digital Experience, Product, and Operational teams to prioritize and implement enhancements to systems, processes, workflows, and customer-facing capabilities.
• Champion a seamless omnichannel experience that combines digital self-service with consultative human interaction.
• Leverage data, analytics, customer feedback, and emerging technologies to improve customer engagement, conversion, onboarding, and retention outcomes.
• Identify opportunities to responsibly leverage AI and automation to improve customer experience, empower employees, increase operational efficiency, and drive business results.
• Drive innovation in sales technology, CRM capabilities, telematics adoption, reporting, and digital engagement to support long-term growth objectives.

Partner Across the Enterprise

• Work closely with leaders across Service, Product, Underwriting, Marketing, Technology, and Digital Experience to improve the end-to-end customer experience.
• Partner with Product and Underwriting teams to align sales strategies with profitability goals, appetite management, and product innovation.
• Support enterprise initiatives focused on customer experience, retention, digital transformation, and long-term growth.
• Serve as a key stakeholder in initiatives that enhance customer outcomes, improve operational effectiveness, and strengthen Plymouth Rock's competitive position.

Build a Culture of Continuous Improvement

• Establish quality assurance standards, coaching frameworks, and performance management processes.
• Leverage analytics and operational insights to identify customer friction points, operational inefficiencies, and growth opportunities.
• Foster a culture of learning, innovation, accountability, and operational excellence.
• Ensure compliance with all applicable insurance regulations and company policies.

Qualifications

• 5+ years of leadership experience within a personal lines insurance contact center, direct-to-consumer insurance operation, brokerage distribution organization, or related insurance environment.
• Demonstrated success leading large teams and delivering measurable improvements in growth, customer experience, operational performance, employee engagement, and business results.
• Experience overseeing customer-facing functions such as sales, service, retention, onboarding, customer experience, operations, or distribution.
• Proven ability to lead complex, multi-functional organizations and drive performance across multiple products, channels, and states.
• Experience leading organizational transformation, operational improvement, customer experience initiatives, or growth strategies.
• Strong understanding of personal lines insurance distribution, contact center operations, customer acquisition, retention, and insurance economics.
• Experience working with CRM platforms, workforce management tools, operational reporting, and performance analytics.

Leadership Competencies

• Proven ability to build, coach, and develop high-performing teams and future leaders.
• Demonstrated ability to develop talent, build leadership capability, and strengthen organizational effectiveness.
• Strong executive presence with the ability to influence and collaborate across all levels of the organization.
• Strategic thinker with the ability to translate vision into execution and deliver results through others.
• Strong business acumen with the ability to balance customer, employee, operational, and financial outcomes.
• Exceptional communication, collaboration, and relationship-building skills.

Education & Licensing

• Bachelor's degree required.
• Active Property & Casualty License preferred.
• Candidates who do not currently hold a Property & Casualty License must successfully obtain and maintain licensure within 90 days of hire as a condition of employment.

Salary Range

The pay range for this position is $164,500 to $218,500 annually. Actual compensation will vary based on multiple factors, including employee knowledge and experience, role scope, business needs, geographical location, and internal equity.

Perks & Benefits

• 4 weeks accrued paid time off, 8 paid national holidays per year, and 2 floating holidays
• Low cost and excellent coverage health insurance options that start on Day 1 (medical, dental, vision)
• Annual 401(k) Employer Contribution
• Free onsite gym and health center at our Woodbridge Location
• Resources to promote Professional Development (LinkedIn Learning and licensure assistance)
• Robust health and wellness program and fitness reimbursements
• Various Paid Family leave options including Paid Parental Leave
• Tuition Reimbursement

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".