Director, Operations Training

About Kin

Kin is redesigning insurance to be smarter, faster, and centered on the customer. We use intelligent pricing, offer seamless bundling, and make every step (from purchasing, servicing to claims) simple and friction-free, especially in the places traditional insurers often ignore.

We empower people to protect what matters most, starting with their homes and expanding to all they value, in a world where climate risks, rising costs, and outdated systems leave too many behind.

Our approach has fostered amazing growth, attracted marquee investors, and earned us accolades, including being named to:

• Built In Chicago's Best Places to Work, Midsize Companies (2021-2025)
• Forbes' America's Best Startup Employers (2021- 2024, Ranked #37 in 2024)
• Inc. 5000 Fastest-Growing Private Companies
• Forbes’ Fintech 50

Simply put, our people are what make us great – we need forward-thinking, inspired game-changers like you to join us in our mission.

The Role: Director of Training

We are seeking a dynamic, results-oriented Director of Training with proven experience developing high-performing sales teams to design, implement, and oversee comprehensive training programs for our Sales and Customer Service agents.

This leader will be responsible for creating impactful onboarding programs, enhancing team capabilities through engaging facilitation, and ensuring all training initiatives directly support organizational goals.

Our vision is for the Director of Training to build and lead a department that consistently produces the strongest sales agents in the insurance industry. While insurance experience is not required, a demonstrated track record of training agents to close sales effectively is essential. The ideal candidate is a master facilitator, an exceptional project manager, and a strategic thinker who can pivot quickly, delegate effectively, and thrive in a fast-paced environment.

What You’ll Do

As the Director of Training, your days will be a dynamic mix of strategy, execution, and team leadership.

• Design and Facilitate Onboarding: Design and facilitate onboarding programs rooted in adult learning principles—ensuring that new hires in Sales and Customer Service ramp quickly and confidently.
• Enhance Team Capabilities: Lead live workshops, coordinate high-impact role-plays, or partner with instructional designers to refresh core content, focusing on delivering training that translates directly into performance.
• Team Leadership: Oversee a team of seven, providing direction, coaching, and development to maximize their effectiveness. Ensure the team remains agile—able to pivot and deploy resources as business needs shift.
• Project Management: Drive multiple training projects from concept to delivery, managing timelines, delegating responsibilities, and tracking results across each initiative.
• Performance Measurement: Own performance measurement—establishing KPIs, analyzing outcomes, and optimizing training programs to close gaps in real time.
• Strategic Alignment: Work closely with Sales and Customer Service leadership to align development plans with business goals and respond quickly when the market or internal needs evolve.
• Build Internal Alignment: Consult with stakeholders on program strategy and shape a roadmap for future enablement efforts, ensuring your impact is both tactical and strategic.

Success in this role is defined by faster onboarding, stronger agent performance, and a company-wide recognition that training is a growth accelerator—not a support function.

Skills to Succeed

• Proven track record in designing and facilitating remote sales onboarding curriculum and training programs that accelerate ramp-up and drive strong Sales performance.
• 7+ years of experience in training and development, including at least 3 years in a Director-level role.
• Experience managing a Learning Management System (LMS).
• Experience with Workday LMS and Rise.

Job Details

• Salary: $135K - $155K
• Location Type: Remote
• Employment Type: FullTime