Plymouth Rock is seeking an innovative and strategically minded Digital Content Strategist to join our Marketing & Communications team. The ideal candidate brings a genuine passion for writing and content creation, a strong editorial sensibility, and a deep understanding of voice and tone. In this role, you will serve as a champion of our brand guidelines and the brand voice authority across three key audience lanes: Agents, Customers, and Sales Enablement. You will produce and oversee compelling, polished copy that supports our marketing objectives and reinforces our brand standards.

Rooted in a commitment to developing and protecting Plymouth Rock's brand voice, this position is primarily writing-focused (70% copywriting, 30% strategy) and is best suited for a seasoned copywriting professional who brings both executional excellence and strategic thinking to their work.

Responsibilities

Copywriting & Brand Voice

Produce, edit, and serve as the final reviewer of copy across all three audience lanes: Agent, Customer, and Sales Enablement, ensuring all content meets established brand, tone, and quality standards prior to distribution
Define and maintain brand voice guidelines for each audience lane, ensuring consistency and alignment across all communications
Function as the team's copy authority, providing structured feedback and upholding editorial standards across channels and programs

Channels & Programs

Develop SEO-optimized web copy in support of content and search strategy
Write and maintain agent profile content
Author press releases and support broader public relations initiatives
Produce internal communications for field and cross-functional audiences
Support program-specific content needs, including Sports Partnerships and Safe Driving initiatives

Strategy & Collaboration

Develop and execute comprehensive content strategies that align with short- and long-term marketing objectives
Collaborate with stakeholders to ensure message consistency and strategic alignment across all touchpoints and audience lanes

AI & Innovation

Lead the adoption and integration of generative AI tools within the content and communications workflow, driving consistency, efficiency, and effectiveness across the team
Establish best practices for AI-assisted content creation that maintain brand integrity and editorial standards

Qualifications

5–7 years of professional copywriting experience, preferably within insurance, financial services, or a similarly regulated industry
Demonstrated ability to develop and adapt copy for multiple audiences and communication contexts
Strong editorial judgment with a track record of elevating copy quality across teams
Working knowledge of SEO best practices and experience writing for search
Experience with PR writing, including press releases and external-facing communications
Hands-on experience with generative AI tools and a proactive approach to leveraging technology in content workflows
Ability to manage multiple priorities and collaborate effectively across functions
A portfolio demonstrating range across marketing copy, long-form content, and communications

Salary Range

The pay range for this position is $90,000 to $115,000 annually. Actual compensation will vary based on multiple factors, including employee knowledge and experience, role scope, business needs, geographical location, and internal equity.

Perks 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

About Plymouth Rock Assurance

Plymouth Rock is a leading northeastern auto and home insurance provider with nearly 40 years of experience, over $2.8 billion in written and managed premium, and nearly 2,500 employees. The company insures more than one million drivers and homeowners across Connecticut, Massachusetts, New Hampshire, New Jersey, New York, and Pennsylvania, combining the local expertise of Independent Agents with the power of doing business online to give consumers the choice to do business the way they want.

Plymouth Rock Assurance

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