Sales Enablement Manager

The Sales Enablement Manager will be responsible for partnering with marketing and sales leadership to help build a sales enablement function within Plymouth Rock’s Independent Agency Auto business. The role calls for a rising leader who will create and implement exceptional programs for onboarding, training, sales productivity, and performance improvements. This role requires continuous cross-functional work with sales leadership, product management and analytics teams to determine enablement priorities to ensure the highest level of business impact.  

This position will support the development of a strategy to help Plymouth Rock’s internal sales team become more effective and efficient in their interactions with our independent agency partners. The role seeks an individual experienced with designing and delivering highly effective programs that focus on improving sales effectiveness, sales productivity, training, and overall sales results. This is an ideal opportunity for a hard-working and proactive sales enablement practitioner eager to take the next step in his or her career by building something from the ground up. The position will initially be an independent contributor with support from instructional designers around the company and with the potential to add junior resources in the future.

Responsibilities: 

• Lead the design, delivery, effectiveness, and continuous improvement of sales enablement programs and content for Plymouth Rock’s internal sales team 

• Become a subject matter expert in our sales processes, sales methodology, and competitive intelligence  

• Build and deliver engaging training sessions with sales teams and sales leaders  

• Lead content creation by partnering with subject matter experts to develop necessary content, including playbooks, pitch decks, case studies, one-pagers, email templates, etc. 

• Oversee content management by: 

• Maintaining a structured and searchable content repository 

• Tagging and categorizing content by use case, staging in the sales process, industry, or persona 

• Regularly audit content for relevance, accuracy, and performance 

• Retire outdated materials and update existing ones to reflect product or market changes 

• Work closely with sales leadership, product management, analytics, and other cross-functional experts to increase collaboration and effectively build awareness and support of sales enablement programs 

• Ensure consistency in branding, tone, and messaging throughout all content and materials 

• Implement the strategy for sales enablement programs and tools 

• Track the success of all sales enablement efforts through both qualitative feedback and quantitative data to continuously improve initiatives 
• Track key success metrics and key performance indicators (KPIs) specific to sales enablement efforts to show return on investment (ROI) and overall impact  

Qualifications:

• Minimum of 4-6 years of sales, sales operations, and/or sales enablement experience with some management experience. Instructional design/teaching experience is a bonus 

• Experience successfully creating and implementing a sales process/methodology with sales playbook initiatives 

• Experience building effective sales onboarding, training, and coaching programs 

• Ability to identify and track metrics that demonstrate improvements in sales productivity 

• Excellent communication skills including public speaking, presentations, teaching, facilitating, and writing  

• Ability to forge relationships across internal organizations and build consensus amid competing priorities 

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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