Events Specialist

Plymouth Rock Assurance • Boston, MA

4d • $70,000 - $95,000 • Hybrid

About The Position

Plymouth Rock Assurance is seeking an Events Specialist to join their Marketing Communications team. This role will be responsible for planning, coordinating, and executing a variety of events, from small executive meetings to large-scale domestic and international experiences. The goal of these events is to strengthen relationships, reinforce the brand, and support business objectives across Marketing, Sales, and Senior Leadership. The position requires strong organizational and communication skills, with the ability to interact with diverse stakeholders. Flexibility for some out-of-office work, including occasional evenings/weekends and travel, is necessary.

Requirements

• 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.
• Competency in Microsoft applications including Word, Excel, and Outlook.
• Bachelor's degree in Event Management, Marketing, Communications, Business Administration, or a related field.

Nice To Haves

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

Responsibilities

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

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

What This Job Offers

• Job Type: Full-time
• Career Level: Mid Level