Agency Experience Lead

Plymouth Rock Assurance•Boston, MA

7h•$70,000 - $105,500

About The Position

At Plymouth Rock, we’re reimagining how independent agents quote, service, and grow their business. As an Agency Experience Lead, you will identify and analyze technology trends, conduct competitive benchmarking, and bring forward recommendations that support the needs of partner agents to influence close rate and be seen as our agents’ carrier of choice. You’ll collaborate with teams across the Marketing, Customer Solutions, Underwriting, Product, Digital, and Claims teams to deeply understand agent workflows and anticipate how technology must evolve to meet shifting industry needs.

Requirements

Bachelor’s degree in Business, Information Systems, Technology, or related field.
5+ years experience in business analysis or technology strategy (insurance experience required).
Direct experience working with or supporting independent insurance agencies, with a deep understanding of their workflows, systems, and operational challenges.
Analytical and critical thinking skills.
Communication skills and ability to work cross-functionally.
Self-motivated, intellectually curious, and passionate about using technology to enhance agent and customer experiences.

Nice To Haves

Strong familiarity with agency management systems, comparative raters, and digital servicing platforms used in the independent channel are strongly preferred.

Responsibilities

Identify process and technology trends to determine how they can be leveraged to create a competitive advantage. This includes a forward-looking perspective on process evolution and anticipating changes in agent workflows and customer expectations.
Support technology roadmap development that aligns with business objectives and positions our systems for future evolution.
Conduct competitive benchmarking to assess where we stand in the market and how competitors are leveraging technology that influence purchase habits.
Evaluate and manage relationships with third-party technology providers (e.g., agency management systems, comparative raters, digital servicing platforms).
Monitor emerging insurtech trends, tools, and startups that could benefit the independent agent channel.
Pilot innovative solutions in partnership with select agencies.
Provide ad hoc analysis and support various strategic business initiatives.
Act as a bridge between business and technical teams, ensuring system enhancements align with the needs of our independent agents and drive measurable improvement.
Lead requirements-gathering sessions with stakeholders and document current and future-state workflows.
Translate business needs into clear requirements, including process flows, user stories, and use cases.
Support User Acceptance Testing (UAT), training, and monitor and evaluate implemented solutions to ensure they meet business outcomes.
Develop communication, training, and adoption strategies to ensure technology is embraced, not just implemented.

Benefits

Paid time off
Free onsite gym at our Boston location
Tuition reimbursement
Low cost and excellent health insurance coverage options that start on Day 1 (medical, dental, vision)
Robust health and wellness programs
Auto and home insurance discounts
Matching donation opportunities
Annual 401(k) employer contribution
Various Paid Family leave options including Paid Parental Leave
Resources to promote professional development
Convenient locations and pre-tax commuter benefits