Contractor Development Lead

Seek Now is looking for a Contractor Development Lead is responsible for coaching and preparing new independent contractors for success in the field performing insurance claim inspections. This role leads contractor onboarding, delivers hands-on instruction in best practices, and ensures contractors are confident, compliant, and ready to meet performance expectations before and after entering the field.

This position may require occasional travel to support field readiness and onboarding activities and involves a flexible work schedule that is not limited to a traditional Monday–Friday workweek.

The ideal candidate is a strong coach, clear communicator, and subject matter expert who enjoys working directly with contractors and supporting their development.

• Coach newly onboarded contractors through orientation and readiness for field-based insurance claim inspections
• Lead onboarding activities, including systems, processes, inspection standards, and documentation expectations
• Prepare contractors for real-world field conditions, quality requirements, and client expectations
• Serve as a primary point of contact for new contractors during early field activity
• Identify skill gaps and provide targeted coaching and corrective guidance
• Partner with Operations and Quality teams to ensure contractor readiness and compliance
• Track onboarding progress and contractor performance during early engagement
• Continuously improve learning materials and onboarding processes
• Support onboarding and readiness activities that may occur outside of standard business hours, based on operational needs
• Travel occasionally, as needed, to support contractor development and field readiness initiatives

• 3+ years of experience in contractor development, training, coaching, claims, inspections, or field operations
• Strong knowledge of insurance claim inspections or similar field-based services (preferred)
• Proven ability to coach, train, and support adults in a professional environment
• Comfortable working with independent contractors in a fast-paced, remote and field-driven setting
• Ability to work a flexible schedule that may include non-traditional hours
• Willingness to travel occasionally, as business needs require
• Strong communication, organization, and follow-through skills
• Proficient with Microsoft Office Suite products

• Contractors complete onboarding efficiently and enter the field well prepared
• Improved early-stage contractor performance, compliance, and quality results
• Positive contractor feedback and engagement throughout the onboarding experience

• health, dental and vision insurance
• 401K with company match
• paid time off (PTO)
• short and long-term disability insurance
• AD&D insurance
• life insurance
• and more!

EEO Statement:

Seek Now is an equal opportunity employer. All aspects of employment including the decision to hire, promote, discipline, or discharge, will be based on merit, competence, performance, and business needs. Seek Now does not discriminate on the basis of race, color, religion, marital status, age, national origin, ancestry, physical or mental disability, medical condition, pregnancy, genetic information, gender, sexual orientation, gender identity or expression, veteran status, or any other status protected under federal, state, or local law.

Other Duties Disclaimer:

This job description is not designed to cover or contain a comprehensive listing of activities, duties, or responsibilities that are required of the employee. Activities, duties, and responsibilities may change or new ones may be assigned at any time with or without notice.