Creative Manager

The Creative Manager – Brand Design & Digital Experience leads the visual expression of Plymouth Rock's brand across both digital and print channels. This role combines hands-on design expertise with people leadership to deliver modern, human, cohesive experiences wherever the brand shows up—on the website, in email and social, in printed materials, internal communications, and out-of-home (OOH) placements such as billboards.
Working closely with Brand Strategy & Operations, Website & Search, and Core Direct marketing teams, this leader translates strategy and insights into high-quality creative that builds the brand and drives performance, with a strong emphasis on digital experiences.

RESPONSIBILITIES

Creative & Design Leadership

• Lead visual direction and execution for campaigns and initiatives across web/landing pages, email, social, display, digital DM, internal communications, printed collateral, and OOH/billboards.
• Turn briefs and brand strategy into clear concepts, layouts, and asset systems that scale across both digital and print channels.
• Ensure design solutions balance brand storytelling, usability, accessibility, readability, and conversion goals.

Team Management & Development

• Manage and mentor a team of three designers, including a Graphic Designer focused on internal communications, printed materials, collateral, and OOH/billboards, and two Digital Designers focused on web, email, and other digital experiences.
• Provide clear creative direction and thoughtful critique that raises the bar on design quality across all channels.
• Build a collaborative culture where designers share work early, iterate, and learn from tests and results.

Design Systems, Templates & Brand Consistency

• Own and evolve the brand design system—components, templates, and patterns—for both digital and print, in partnership with Website & Search and production/development partners.
• Maintain brand guidelines for color, typography, imagery, iconography, motion, and print standards (sizes, specs, file formats).
• Ensure consistent application of the brand across all materials, from landing pages and emails to internal posters, sales collateral, and billboards.

Experience Design & Collaboration

• Partner with Website & Search to design page layouts and modules that support key digital journeys (quotes, self-service, education).
• Collaborate with Performance marketing/Email teams to develop modular email templates and campaign designs that support personalization and testing.
• Ensure internal communications developed by graphic designer (e.g. flyers, posters, presentations, and brochures) are clear and on-brand.
• Coordinate with Media, Product, and agencies on creative specs and asset requirements for digital, print, and OOH placements and ensure smooth handoffs.

Testing, Performance & Process

• Review performance of digital creative (e.g., CTR, engagement, conversion) with Analytics and channel owners and factor learnings back into design decisions.
• Propose and execute creative tests (layouts, imagery, hierarchy, motion vs. static, formats) and roll winning patterns into standards and templates.
• Collaborate with Project Manager/Ops to ensure assets are delivered on time, on spec, and technically sound.

QUALIFICATIONS

• Bachelor's degree in graphic design, visual communications, digital media, or related field (or equivalent portfolio/experience).
• 7–9+ years of experience in brand and visual design across both digital (web, email, social, display) and print/OOH; 2–3+ years in a senior or lead designer role.
• Strong portfolio of modern, responsive digital work and well-executed print/OOH or collateral, demonstrating consistent brand systems.
• Proficiency with Figma and Adobe Creative Cloud; familiarity with HTML/CSS and digital production standards sufficient to collaborate with developers and vendors.
• Experience working within or building design systems and templates that span digital and print.
• Solid understanding of UX/UI best practices, web standards, accessibility, and practical print/OOH production requirements (file prep, specs, color, resolution).
• Proven ability to manage multiple projects and deadlines, and to give/receive feedback effectively.
• Strong communication skills; comfortable presenting work and rationale to non-design stakeholders, including senior leaders.

SALARY RANGE

The pay range for this position is $113,000 to $ 154,000 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 + 9 paid national holidays per year
• 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".

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