Sales Training & Operations Supervisor

The Sales Training & Operations Supervisor is responsible for leading the Training and Operations functions that support the performance, growth, and operational effectiveness of Plymouth Rock’s Direct Sales organization. This role oversees the development and execution of new-hire onboarding, licensing, continuing education, sales enablement, operational readiness, technology implementation, carrier support, quality and compliance initiatives, and ongoing employee development. The Supervisor partners closely with Sales leadership and cross-functional teams to ensure representatives have the knowledge, tools, systems, processes, and support necessary to deliver strong sales results and an exceptional customer experience. The Supervisor will lead a team of Training and Operations professionals while serving as a key business partner to Sales leadership, Technology, Product, Underwriting, Service, Legal/Compliance, Human Resources, Marketing, Workforce Management, and external carrier partners.

RESPONSIBILITIES

Training, Onboarding & Employee Development

• Lead the Sales Center training strategy, including new-hire onboarding, licensing, product training, sales development, continuing education, system training, and ongoing employee development.
• Manage and develop Sales Trainers, Property & Casualty instructors, Operations Team Leaders, and other Training and Operations employees.
• Continuously evaluate and improve training curriculum, delivery methods, testing, certification standards, and learning technology to improve employee readiness and reduce the time required for new hires to reach veteran-level performance.
• Partner closely with Sales Supervisors to monitor new-hire performance following formal training and identify opportunities related to call-to-quote performance, close rate, quality, customer experience, product knowledge, system proficiency, and salesmanship.
• Establish clear performance benchmarks throughout the onboarding process and use data to identify employees requiring additional development or intervention.
• Ensure training programs evolve with changes in products, states, carrier offerings, technology, compliance requirements, customer expectations, and Sales Center strategy.
• Maintain and enhance learning platforms and digital enablement tools, including LMS platforms, WalkMe, knowledge resources, AI-enabled training solutions, and other learning technologies.
• Maintain a customer-first approach when evaluating training, processes, systems, and operational workflows.
• Partner with Sales, Service, Product, Underwriting, and Technology to identify opportunities to reduce customer effort and improve the end-to-end customer experience.
• Support analysis and improvement efforts related to customer onboarding, calls-to-PIF, first-sales resolution, early customer contacts, cancellations, retention, transfers, and other customer journey opportunities.
• Use performance data, QA results, call observations, employee feedback, and customer trends to identify opportunities for targeted training and development.
• Partner with Sales Supervisors and Team Leaders to ensure training and coaching priorities remain aligned and that development continues after employees transition from formal training to the sales floor.

Sales Operations & Operational Readiness

• Lead Sales Center operational readiness for new products, states, carriers, systems, workflows, and business initiatives.
• Develop and maintain scalable operational processes that improve representative efficiency, customer experience, compliance, and business performance.
• Coordinate onboarding, system access, appointments, licensing, and other operational requirements necessary for employees to successfully perform their roles.
• Oversee employee lifecycle operational activities including new hires, transfers, terminations, system access changes, and carrier appointments.
• Identify process inefficiencies and operational friction affecting representatives or customers and partner with appropriate teams to develop solutions.
• Ensure Sales leadership and frontline employees are appropriately prepared for upcoming business, system, product, and process changes.

Technology & Digital Enablement

• Serve as a primary Sales business partner to Technology for system enhancements, defects, workflow improvements, and operational issues impacting the Sales Center.
• Partner with Sales leadership and Technology teams to identify and prioritize system enhancements that improve representative productivity, sales effectiveness, and customer experience.
• Oversee the defect-management process for Sales-related technology issues, including identification, documentation, prioritization, tracking, testing, validation, and business communication.
• Coordinate and/or lead User Acceptance Testing for Salesforce, quoting platforms, carrier systems, call-center technology, and other Sales applications.
• Identify opportunities to responsibly leverage AI and automation to improve employee development, workflow efficiency, knowledge access, coaching, and customer experience.

Licensing, Compliance & Quality

• Oversee Property & Casualty licensing strategy and compliance for the Sales Center, including new licenses, renewals, continuing education, state expansion, and carrier appointments.
• Ensure licensing requirements are completed accurately and within required timelines.
• Maintain appropriate controls and reporting to ensure Sales employees remain compliant with state, carrier, and company licensing requirements.
• Partner with Legal/Compliance and Sales leadership on regulatory requirements, audits, document retention, training, and operational controls.
• Identify recurring quality or compliance trends and develop solutions to address root causes through training, process improvement, technology, or communication.

Carrier & Product Support

• Serve as a key operational contact for third-party carrier partners and support carrier onboarding, appointments, workflows, system access, training, and ongoing operational requirements.
• Partner with Product and Underwriting teams to ensure Training and Operations remain aligned with product changes, underwriting appetite, eligibility requirements, and new business initiatives.
• Support expansion into new states, products, and carrier partnerships by coordinating training, licensing, system readiness, operational workflows, and employee communications.
• Provide feedback to Sales leadership, Product, Underwriting, and carrier partners regarding recurring employee and customer friction, competitive trends, eligibility issues, and operational opportunities.

QUALIFICATIONS

• 5+ years of experience in personal lines insurance, Sales Operations, Training, Sales Enablement, contact center operations, or a related field preferred.
• Prior leadership experience with demonstrated ability to coach, develop, and manage employees.
• Bachelor’s degree from an accredited four-year college or equivalent combination of education and relevant work experience preferred.
• Active Property & Casualty Insurance license required based on business needs.
• Strong understanding of personal lines insurance products, sales processes, customer onboarding, licensing, compliance, and contact-center operations.
• Demonstrated ability to manage multiple projects and priorities in a fast-paced environment while maintaining strong attention to detail and meeting deadlines.
• Strong analytical and problem-solving skills with the ability to use data to identify trends, determine root causes, and develop practical solutions.
• Strong written and verbal communication skills with the ability to communicate effectively with frontline employees, leadership, business partners, and external carriers.
• Demonstrated ability to influence outcomes and lead initiatives across teams without direct authority.
• Ability to balance strategic priorities with day-to-day operational responsibilities.
  
  

SALARY RANGE

The pay range for this position is $100,000 to $133,000 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 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”.