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Plymouth Rock Assurance Head of Home Insurance Direct Marketing in Boston, Massachusetts

Plymouth Rock Assurance is seeking a seasoned Direct Marketing leader to drive the management and profitable growth of Plymouth Rock’s Home insurance business in our direct-to-consumer (DTC) distribution channel. Plymouth Rock Assurance has recently launched a new and modern product solution for home insurance, enabling customers and partners to obtain a home insurance quote in just seconds – a revolutionary way to buy Home insurance. We are seeking a direct marketing professional to join what is becoming one of the strongest Home Insurance teams in the industry, with a focus on driving consumer demand for an industry-leading and differentiated product.

The leader of DTC marketing will be responsible for the development, execution, and optimization of all aspects of DTC marketing initiatives in the company’s home insurance business division, including but not limited to: creative and messaging development and execution, budgeting and forecasting of sales by marketing channel, expense budgeting, media planning and execution, and forecasting impact on demand, margin and other metrics. As a senior leader on the home marketing team reporting to the CMO, this newly created position will build and execute a strategy that drives efficient and profitable growth for a rapid-growing and critically important business within the enterprise.


  • Responsible for the execution and optimization of consumer demand generation through the use of addressable integrated multi-media tactics including addressable digital, and traditional channels including direct mail

  • Responsible for DTC new business planning, forecasting, and portfolio management of mix of marketing channels to achieve core objectives of growth and profit

  • Accountable for building a marketing engine to drive continuous marketing spend efficiency, which includes infrastructure, processes, robust testing strategy, and analytics

  • Maximize return on investment of marketing spend by optimizing marketing channels and achieving operational efficiencies

  • Partner with internal and external analytics teams to optimize marketing programs, creative strategy, audience targeting/modelling, and incremental analysis of marketing programs

  • Accountable for the development of value proposition, key messages, proof points, creative and brand stewardship to be integrated into acquisition marketing and sales operations

  • Coordination with internal stakeholders to drive the business, including product, legal, and IT

  • Operate as a member of the senior marketing management team; provide guidance and direction on direct marketing strategic initiatives and mentorship to other resources

  • Develop future staffing plan to build the future DTC team as the business grows

Experience and Requirements

  • 7+ years of experience leading direct marketing with responsibility for investment decisions and managing return on investment, with a track record of delivering year over year improvement in top line revenue growth and marketing efficiency.

  • 5+ years in a leadership role with a strong background in multi-channel marketing media planning execution with an emphasis on addressable digital marketing and traditional marketing; seasoned in creating, managing, and optimizing acquisition campaigns.

  • Very strong analytical abilities; experience interpreting data to generate insights that inform investment decisions and marketing strategy; experience developing and reporting on metrics and KPIs for business goals, process improvements and campaign management.

  • Confidence in building a rapport with and nurturing good working relationships; strong collaborator who can build relationships in a matrix environment; ability to build strong relationships with internal stakeholders, external partners, including experience with managing media buying agencies and other third-party vendors.

  • Results oriented with excellent planning, prioritization and decision-making skills; works well under pressure and delivers on commitments with little direction.

  • Excellent written and verbal communication and presentation skills; ability to communicate effectively with a diverse technical and non-technical audiences.

  • Ability to communicate effectively to both technical and non-technical audiences.

  • Comfortable working in a fast-paced, ever-changing start-up like environment.

About the Company

The Plymouth Rock Company and its affiliated group of companies write and manage over $1.6 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”.

Job ID: 2022-3127

External Company URL:

Street: 695 Atlantic Ave