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 enga