Contractor Development Lead

Seek Now • Louisville, KY

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About The Position

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.

Requirements

• 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

Nice To Haves

• Strong knowledge of insurance claim inspections or similar field-based services (preferred)

Responsibilities

• 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

Benefits

• Seek Now offers a great benefit package, which includes 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!

What This Job Offers

• Job Type: Full-time
• Career Level: Mid Level
• Education Level: No Education Listed