Events Specialist

Plymouth Rock Assurance is a leading personal lines insurance carrier committed to exceptional service and innovative solutions. Our Marketing Communications team brings this to life through a best-in-class events program, ensuring agents, partners, and customers experience More Than Just Insurance. 

We're looking for an Events Specialist to help plan, coordinate, and execute memorable events ranging from small executive meetings to large-scale, multiday domestic and international experiences that strengthen relationships, reinforce our brand, and support business goals across Marketing, Sales, and Senior Leadership. 

This role sits at the intersection of Marketing, Field Operations, Executive Leadership, and external partners, and may involve guiding junior team members. You should be detail-oriented, proactive, and comfortable communicating with everyone from hotel coordinators to internal executives. The role requires some out-of-office flexibility, including onsite event support, occasional evenings/weekends, and travel of 10–15%. 

Responsibilities:

Events Support & Coordination 

• Support and lead a comprehensive event strategy aligned with business priorities and brand positioning. 

• Maintain the annual events calendar and contribute to performance/investment reporting for leadership. 

• Follow and help refine best practices and standards for event production. 

Event Design & Execution 

• Lead the design and execution of multiday events centered around incentive travel, corporate meetings, golf/sports outings, and agent engagement experiences. 

• Ensure events are innovative, on-brand, and detail-driven. 

• Coordinate logistics from sourcing through onsite execution. 

Operational & Vendor Coordination 

• Build and maintain relationships with venues, hospitality partners, production teams, and transportation providers. 

• Own vendor communications, contract review, and performance tracking. 

• Create event timelines, run-of-show documents, staffing plans, and delivery schedules. 

Budget & Performance Support 

• Manage event budgets across a portfolio of events, flagging cost-efficiency opportunities and communicating recommendations to leadership. 

• Support performance analysis, attendee feedback, and ROI reporting. 

Team & Cross-Functional Collaboration 

• Partner with field teams and leadership to align on event goals. 

• Collaborate with Marketing Communications on branded materials, promotional items, and attendee communications. 

• Support internal and external partners to ensure flawless execution. 

Onsite Support 

• Serve as onsite lead or support lead, managing logistics and resolving issues. 
• Travel 10–15% for setup, coordination, and onsite support.

Qualifications:

• 5-7 years of prior event planning experience, preferably in a corporate or hospitality setting.  

• Willingness to travel locally, regionally, and internationally. Passport required. (10–15%, including occasional evenings and weekends)  

• Strong organizational and coordination skills with demonstrated ability to support multiple initiatives simultaneously.  

• Experience assisting with vendor communications and managing budgets.  

• Excellent verbal, written, and in-person communication skills, with the ability to collaborate effectively across teams and with senior leadership.  

• Highly organized, detail-oriented, and proactive with an interest in improving operational efficiency.  

• Able to work autonomously and collaboratively in a fast-paced, ever-changing environment.  

• Ability to balance day-to-day execution with support for broader strategic initiatives.  

• Experience in hospitality is a plus, demonstrating a passion for delivering exceptional guest experiences.  

• Competency in Microsoft applications including Word, Excel, and Outlook. Experience in Wordpress, CrowdComms, and SmartSheets is a plus.  

• Bachelor's degree in Event Management, Marketing, Communications, Business Administration, or a related field.  

The pay range for this position is $70,000 to $95,000 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 + 10 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 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”

#LI-SM1