Who We Are
Chesapeake Employers’ Insurance Company is a purpose-driven organization dedicated to improving the lives and livelihoods of our policyholders, injured workers, team members, and the community. As a leading workers' compensation specialty insurer in the mid-Atlantic region, we take pride in being a force for good. Our 350 team members are committed to making a positive impact every day in the lives of all our stakeholders. Join our motivated, professional team as we foster a culture of values, teamwork, innovation, and collaboration. Established in 1914, Chesapeake Employers Insurance, headquartered in Towson, Maryland, has over a century of experience, a strong financial foundation, and an "A" rating from AM Best.
Lead growth. Shape strategy. Drive results.
The Director of Sales Operations plays a pivotal role in advancing Chesapeake’s growth strategy within the Workers’ Compensation market serving Maryland and across the Mid-Atlantic by advancing sales operations, empowering teams, and strengthening channel relationships. This is a high impact leadership role for a strategic, data driven leader. In partnering across the business, you’ll turn insight into action driving performance while delivering on Chesapeake’s commitment to purpose, people, and results.
POSITION SUMMARY:
The Director of Sales Operations plays a critical role in advancing Chesapeake’s growth strategy within the Maryland Workers’ Compensation market. This role is responsible for leading the design, execution, and continuous improvement of the sales infrastructure to drive profitable growth, strengthen agent and channel partnerships, and enhance the overall policyholder experience.
The Director provides strategic leadership and operational excellence by aligning people, processes, and technology to support business objectives. Through data-driven insights and collaboration across Marketing, Underwriting, Finance, and Premium Audit, this position ensures that the sales organization is equipped to deliver exceptional service, achieve production goals, and sustain long-term, profitable growth, reflecting Chesapeake’s commitment to purpose, people, and performance.
DUTIES AND RESPONSIBILITIES:
Sales Strategy & Execution
· Develop and execute strategic sales plans that drive profitable growth across
Commercial Insurance and Workers’ Compensation markets.
· Partner with Chief Growth Officer to align sales objectives with broader
organizational goals and market expansion initiatives.
· Continuously assess market trends, competitor strategies, and emerging
opportunities to refine go-to-market plans.
B2B Agent & Channel Management
· Strengthen relationships with independent agents to increase market insight and
retention.
· Design and manage tiered incentive programs, co-marketing initiatives, and distribution strategies that enhance partner engagement.
· Evaluate agent performance metrics and provide insights to improve production, profitability, and service quality.
Sales Planning & Forecasting
· Oversee territory design, quota setting, and forecasting to ensure fair distribution of opportunities and accurate pipeline visibility.
· Utilize data-driven tools and analytics to predict revenue trends and proactively address performance gaps.
Operational Excellence
· Optimize the sales lifecycle from lead generation to deal closure by streamlining processes and removing inefficiencies.
· Standardize workflows, reporting structures, and best practices across regions and sales functions.
Cross-Functional Collaboration
· Work closely with Marketing, Premium Audit, Finance, and Underwriting to ensure cohesive go-to-market alignment and strategic execution.
· Translate business needs into actionable sales initiatives, campaigns, and growth projects.
· Facilitate regular cross-departmental meetings to maintain visibility and accountability for sales priorities.
Analytics & Performance Management
· Develop and maintain advanced dashboards and KPIs to track productivity, conversion rates, and revenue growth.
· Use predictive analytics to identify performance trends, gaps, and optimization opportunities.
· Present data-driven insights and recommendations to executive leadership to inform strategic decisions.
Sales Technology & Systems Oversight
· Lead the implementation and optimization of CRM and related tools (Salesforce, Tableau, Power BI) to enhance visibility and efficiency.
· Partner with IT team to ensure data integrity, functionality, and user adoption across the sales organization.
Team Leadership & Development
· Build, mentor, and lead a high-performing Sales & Sales Operations functions focused on execution, collaboration, and accountability.
· Establish individual and team performance goals with clear success metrics.
· Foster a culture of learning, innovation, and continuous improvement through coaching and development programs.
Process & Policy Governance
· Develop, document, and enforce standard operating procedures to ensure consistency and compliance across sales operations.
· Collaborate with Legal, Compliance, and HR to uphold ethical and regulatory standards.
Budgeting & Resource Allocation
· Develop, manage, and monitor annual sales operations budgets aligned to revenue targets and strategic priorities.
· Evaluate resource allocation across regions to optimize coverage, reduce redundancies, and maximize ROI.
· Provide financial analysis and performance reporting to inform leadership decision-making.
SKILLS, EDUCATION AND EXPERIENCE:
Education:
· bachelor’s degree in business administration, Marketing, or a related field required; Master’s degree (MBA) preferred.
Experience:
· Minimum 10 years of progressive sales or sales operations experience, including at least 5 years in a leadership capacity.
· Proven success in Commercial Insurance and/or Workers’ Compensation sales environments with a strong understanding of B2B agent distribution models and channel partner ecosystems.
· Demonstrated experience building and scaling high-performing sales teams and implementing operational frameworks that improve revenue performance.
Technical Expertise:
· Advanced proficiency in CRM and data analytics platforms (Salesforce, Power BI, Tableau, Excel).
· Strong analytical skills in forecasting, pipeline analysis, and performance measurement.
Leadership & Communication:
· Exceptional leadership, collaboration, and communication skills with the ability to influence cross-functional stakeholders and executive teams.
· Strong project management, problem-solving, and decision-making capabilities in fast-paced, growth-oriented settings.
Industry Knowledge:
· Deep understanding of commercial insurance distribution dynamics, underwriting partnerships, and workers’ compensation markets.
· Knowledge of regulatory frameworks, compliance, and agency operations within insurance environments.
POSITIONAL COMPETENCIES:
- Strategic Mindset
- Insurance Acumen
- Operational Excellence
- Analytical Insight
- Financial Management
- Collaboration & Influence
- Technical Adaptability & Digital Fluency
- Integrity & Accountability
- Leadership & Team Development
PHYSICAL DEMANDS:
While performing the duties of this job, the teammate is regularly required to sit, use hands to finger, handle or feel objects, tools or controls; reach with hands and arms. The teammate is occasionally required to stand, walk, stoop, kneel, crouch or crawl. The teammate may occasionally lift to 20 pounds. Specific vision abilities are required, which include, close vision, peripheral vision and the ability to adjust focus. On occasion the incumbent will be required to travel off premises and must possess a valid Maryland driver’s license.
WORK ENVIRONMENT:
Office environment. The noise level is usually moderate. Hybrid Work is available for those that qualify.
What We Offer
We offer a competitive benefits package that includes health, vision, and dental coverage, a robust PTO plan, an 8% employer contribution to retirement regardless of team member contribution, educational assistance, and opportunities to participate in team member appreciation events. Additionally, we provide STD, LTD and group life insurance 1X a team members salary. You'll also enjoy free tickets to community attractions, all part of our commitment to providing a high quality of work life. You will have the flexibility to thrive in a hybrid work environment and an opportunity to participate in development and volunteer programs.
