Join Plymouth Rock Assurance as a Marketing Cloud & Automation Specialist, a hands-on role supporting our Home (homeowners insurance) Marketing team across all three of its channels: Independent Agent, Partner, and Direct (Direct-to-Consumer), with communications that reach independent agents, partner organizations, and consumers. Based in our Boston office and reporting to the Marketing Operations & Automation Supervisor, this position focuses on building, testing, and maintaining email campaigns and automated journeys in Salesforce Marketing Cloud; supporting audience segmentation and performance measurement; and using AI tools to design and build automated processes that improve quality and efficiency across the team.

Responsibilities

Email Template Development

Build and maintain responsive email templates using HTML, CSS, and AMPscript within Salesforce Marketing Cloud, using Litmus for quality assurance (QA) and rendering checks.
Help ensure templates meet quality standards for rendering, accessibility, and load performance across devices, email clients, and mailbox providers (e.g., Gmail, Outlook).
Partner with creative and marketing teams to apply dynamic content, personalization rules, and brand standards to templates.
Contribute to a modular template library (components, content modules, and versioning) that speeds up production and reduces rework.

Campaign & Journey Builds

Build, QA, and deploy automated and triggered campaigns and journeys for the Independent Agent, Partner, and Direct channels, from requirements intake through launch and monitoring.
Build and maintain dynamic content blocks to support segmentation and personalized messaging, including rules and fallback logic.
Write SQL queries and work with data extensions and data relationships to build campaign audiences.
For the Direct channel, focus on campaign builds, including audience setup, personalization, and QA, in partnership with the channel’s campaign owners.
Work with CRM, Analytics, and channel marketing teams to make sure tracking requirements, data capture, and measurement are set up correctly.
Manage multiple concurrent builds across the three channels, and communicate timelines, dependencies, and tradeoffs clearly to stakeholders.

AI & Process Automation

Use AI tools (such as Claude) to design and build automated quality control (QC) processes, checklists, and validation steps that catch errors before campaigns launch.
Identify manual, repetitive steps in campaign production and data workflows, and help build automated solutions to reduce them.
Test, document, and maintain automated processes so they are reliable and easy for the team to use.
Handle customer and agent data responsibly, and build AI-assisted processes within company IT security and data privacy guidelines.
Participate in evaluating new AI and automation capabilities and share practical ideas for applying them in marketing operations.

Testing & Optimization

Set up and execute A/B tests across templates, subject lines, creative assets, offers, and CTAs.
Participate in analyzing test results and help translate findings into recommendations.
Support the use of AI-driven features (e.g., Einstein) for send-time optimization and targeting.

Compliance, Deliverability & Performance

Follow digital communication standards (CAN-SPAM, TCPA) and internal governance in all builds.
Participate in performance monitoring for assigned programs and journeys, including deliverability, engagement, and conversion health checks.
Track campaign KPIs through dashboards and reports, and flag underperformance or issues early.

Documentation & Collaboration

Create and maintain documentation of processes, templates, and best practices, including QA checklists, naming conventions, and build workflows.
Help team members with template usage and Marketing Cloud questions.
Provide input on feasibility and effort for new campaign and automation requests.

What Success Looks Like

Within 60 days: independently building, testing, and deploying emails and journeys in Salesforce Marketing Cloud using team standards and QA checklists.
Within 90 days: delivering your first automated QC or workflow process that reduces manual effort or catches errors before launch.
Within 6 months: serving as a dependable builder across the Independent Agent, Partner, and Direct channels, and contributing improvements to templates, documentation, and automation.

Required Qualifications

2–4 years of hands-on experience in email development or Salesforce Marketing Cloud.
Proficiency in HTML and CSS for building responsive email templates.
Hands-on experience with Salesforce Marketing Cloud, including building emails, journeys, and automations.
Working knowledge of AMPscript for personalization and SQL for segmentation and reporting.
Understanding of email marketing best practices, including personalization, testing, and accessibility.
Strong attention to detail and a quality-first approach to building and testing.
Ability to manage multiple requests at once and keep stakeholders informed on status and timelines.
Strong collaboration skills and the ability to explain technical concepts to non-technical stakeholders.

Preferred Qualifications

Bachelor’s degree in Computer Science, Information Technology, Marketing, or a related field.
Salesforce Marketing Cloud certification (Email Specialist, Developer, or Administrator).
Experience using AI tools (such as Claude) to automate workflows and improve quality control.
Experience with Python or another scripting language, and advanced Excel skills.
Familiarity with Litmus and Salesforce Einstein.
Experience supporting multi-channel or lifecycle marketing programs; exposure to insurance or to agent, partner, or direct channels is a plus.

Why Work For Us

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

Salary Range: $78,000 to $103,500 a year. Actual compensation will vary based on multiple factors, including employee knowledge and experience, role scope, business needs, geographical location, and internal equity.

About The Company

The Plymouth Rock Company and its affiliated group of companies write and manage over $2.0 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 2,000 people and is headquartered in Boston, Massachusetts. Plymouth Rock Assurance Corporation holds an A.M. Best rating of “A-/Excellent”.

Plymouth Rock Assurance

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Marketing Cloud and Automation Specialist