Job Description: Director of Contractor Operations

The Director of Contractor Operations is a leadership role responsible for developing and executing the strategic vision for Westhill’s contractor network. Reporting to the Vice President of Operations, this role provides oversight, direction, and innovation across all facets of contractor recruiting, onboarding, credentialing, and contractor network oversight. The Director will build and lead a high-performing team, drive operational excellence, and ensure Westhill contractors are positioned to deliver superior service to carrier partners and customers.

This position requires a strategic thinker with strong operational expertise, proven leadership skills, and the ability to influence cross-functional initiatives that scale and strengthen Westhill’s contractor ecosystem.

• Provide strategic leadership for the Contractor Operations function, setting the long-term vision and roadmap in alignment with Westhill’s organizational goals.
• Lead, mentor, and inspire a growing team.
• Foster a culture of accountability, innovation, and continuous improvement across all operational processes.
• Partner closely with senior leadership (Operations, Contractor Performance, BI/Analytics, QA, Training, etc.) to ensure contractor operations align with carrier needs and business objectives.
• Build workforce capacity and succession plans to support long-term scalability of the contractor network.

• Oversee national recruiting strategy to ensure geographic, trade, and skillset coverage to meet partner and customer demand.
• Optimize onboarding frameworks that reduce time-to-activation while enhancing contractor engagement and retention.
• Ensure all credentialing, licensing, insurance, and compliance processes are consistently applied and monitored.
• Drive standardization of best practices across Recruiting and Onboarding, balancing contractor experience with compliance requirements.

• Define, implement, and evolve KPIs, scorecards, and dashboards to evaluate contractor performance, capacity, and compliance.
• Leverage analytics to forecast capacity needs, identify gaps, and prioritize recruiting and training initiatives.
• Collaborate with BI and Performance teams to translate complex data into actionable strategies for continuous improvement.
• Oversee operational efficiency projects, ensuring technology and process enhancements improve scalability and contractor success.

• Partner with Training (Westhill University) to ensure contractors receive the tools and resources to succeed.
• Partner with our Customer Experience team to collaborate on continuity of contractor performance and capacity.
• Collaborate with carrier partners to align network capacity and performance to evolving program requirements.
• Drive innovation by identifying opportunities for process automation, workflow optimization, and contractor experience improvements.

• 10+ years of experience in operations leadership, contractor/vendor management, or related field.
• Proven ability to design and execute operational strategies at scale, balancing compliance, efficiency, and partner experience.
• Strong leadership skills with demonstrated success in building and managing high-performing teams.
• Exceptional analytical, problem-solving, and decision-making skills, with the ability to translate data into actionable strategies.
• Excellent communication and relationship-building skills, with the ability to influence stakeholders at all levels.
• Experience working within the property & casualty insurance ecosystem or related contractor/vendor networks strongly preferred.
• Proficiency with data analysis tools, performance dashboards, and operational workflow systems.

The Director of Contractor Operations is accountable for the health, scalability, and performance of Westhill’s contractor network. By driving strategy, optimizing processes, and leading a high-performing team, this role ensures contractors are positioned to succeed—ultimately delivering superior outcomes for carrier partners, contractors, and policyholders alike.