Director of Sales Operation

Chesapeake Employers' Insurance Company • Towson, MD

6h • Hybrid

About The Position

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.

Requirements

• bachelor’s degree in business administration, Marketing, or a related field required
• 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.
• Advanced proficiency in CRM and data analytics platforms (Salesforce, Power BI, Tableau, Excel).
• Strong analytical skills in forecasting, pipeline analysis, and performance measurement.
• 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.
• Deep understanding of commercial insurance distribution dynamics, underwriting partnerships, and workers’ compensation markets.
• Knowledge of regulatory frameworks, compliance, and agency operations within insurance environments.

Nice To Haves

• Master’s degree (MBA) preferred.

Responsibilities

• 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.
• 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.
• 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.
• 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.
• 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.
• 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.
• 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.
• 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.
• 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.
• 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.

Benefits

• health, vision, and dental coverage
• a robust PTO plan
• an 8% employer contribution to retirement regardless of team member contribution
• educational assistance
• opportunities to participate in team member appreciation events
• STD, LTD and group life insurance 1X a team members salary
• free tickets to community attractions
• flexibility to thrive in a hybrid work environment
• opportunity to participate in development and volunteer programs

What This Job Offers

• Job Type: Full-time
• Career Level: Director
• Number of Employees: 101-250 employees