Head of Strategic Partnerships

Plymouth Rock Home Assurance is seeking an experienced, strategic, and highly motivated Head of Strategic Home Partnerships to accelerate the growth of our fast-scaling Home Insurance business.

Plymouth Rock’s innovative @Home product is redefining how customers and partners experience homeowners insurance by combining speed, simplicity, and exceptional service. Offered across six states in the Northeast and growing faster than the industry, our Home business operates like a start-up within an established, trusted insurance company. We are a dynamic, entrepreneurial team committed to building a better way to protect homes and the people in them.

About the Role

The Head of Strategic Home Partnerships will lead the strategy, development, and management of high-impact partnerships that fuel Plymouth Rock’s next phase of Home growth. This role is responsible for sourcing, structuring, and optimizing relationships across a diverse portfolio of partners, including major P&C distributors, carriers, affinity brands, and emerging digital platforms.

As a senior leader within the Home business, you will work cross-functionally with Product, Technology, Service, and Finance teams, as well as executive leaders across the enterprise, to deliver mutually beneficial partnerships that drive innovation, differentiation, and profitable growth.

Responsibilities:

• Lead partnership strategy and execution
  Own the full partnership lifecycle from opportunity identification and contract negotiation to long-term relationship management and performance optimization.
• Drive profitable growth
  Develop and execute partnership business plans and KPIs aligned with enterprise objectives, delivering sustainable and measurable growth.
• Foster strong, collaborative relationships
  Build and maintain trusted relationships with key partners, including large P&C carriers, distributors, and alternative digital and brand partners.
• Inspire and develop a high-performing team
  Lead and coach a team focused on innovation, accountability, and measurable results.
• Collaborate across the enterprise
  Partner closely with Product, Technology, Marketing, and Service teams to ensure seamless partner experiences and operational excellence.
• Champion innovation and continuous improvement
  Identify and implement strategies that enhance partner profitability, efficiency, and scalability.
• Serve as a senior marketing team leader
  Contribute to marketing strategy, mentor colleagues, and represent the Home business across the Plymouth Rock organization.

Qualifications: 

• 8+ years of experience in business development, partnerships, sales, or marketing leadership, ideally within P&C insurance, insurtech, or financial services.
• Proven success in negotiating and managing large-scale partnerships that deliver meaningful business outcomes.
• Analytical, data-driven decision-maker with a track record of using insights to inform strategy and drive performance.
• Exceptional communication, presentation, and negotiation skills with the ability to influence and build trust with executives, partners, and cross-functional teams.
• Strategic thinker who thrives in ambiguity and can turn ideas into action.
• Collaborative leader with experience navigating matrixed organizations.
• Comfortable operating in a fast-paced, entrepreneurial environment where innovation and agility are key.
• Willingness to travel up to 30%.

Salary Range:​

The pay range for this position is $155,000 to $224,000 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 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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