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Operations Training Manager, Delivery

Job in Chicago, Cook County, Illinois, 60290, USA
Listing for: Kin Insurance
Full Time position
Listed on 2026-07-17
Job specializations:
  • Management
    Professional Development
Salary/Wage Range or Industry Benchmark: 110000 - 170000 USD Yearly USD 110000.00 170000.00 YEAR
Job Description & How to Apply Below

Quick Summary

Lead Kin’s Operations training delivery function—developing trainers, scaling onboarding programs, and ensuring high-impact learning experiences that accelerate performance across Operations teams.

The opportunity

We’re looking for an Operations Training Manager to lead the training delivery and facilitation function for Kin’s Operations Training team. As Kin continues to scale, strong onboarding, enablement, and continuous learning are critical to ensuring our Operations teams deliver exceptional service and performance.

In this role, you’ll oversee a team of trainers responsible for delivering engaging, high-impact learning experiences for both new hires and tenured Operations team members, consisting of licensed sales agents and customer service representatives. You’ll partner closely with operational leaders to identify knowledge gaps, translate business needs into effective learning solutions, and ensure our training programs evolve alongside the business.

This leader acts as a strategic bridge between Operations and Training—ensuring the right programs, facilitation approaches, and learning strategies are in place to support operational excellence and team development.

Your responsibilities
  • Lead and manage the Operations learning delivery function, ensuring consistent, high-quality delivery of onboarding ~200 new hires annually, and continuous learning programs for our existing front line teams
  • Develop and coach a team of 3-5 facilitators, providing performance management, mentorship, and professional development
  • Own and manage the Operations training calendar and team capacity, aligning training schedules with hiring plans, operational priorities, and program capacity
  • Partner with Operations leaders to identify knowledge gaps, emerging skill needs, and opportunities for targeted learning interventions
  • Translate operational feedback and performance trends into actionable training improvements and new learning initiatives, while running continuous evaluation of all programs and team members
  • Partner with nesting managers from Sales and Service to identify recurring knowledge gaps and translate them into targeted training interventions
  • Collaborate with the Instructional Design Manager on course strategy, content structure, and learning methodology
  • Monitor trainee performance trends and operational metrics to evaluate training effectiveness and continuously improve programs, along with ensuring 100% CE completion across our teams
  • Support and contribute to leadership development initiatives for Operations leaders and emerging managers
  • Facilitate training sessions ~30% of time to support trainer capacity or high-priority initiatives
Success in this role

In your first 6–12 months at Kin, success is less about checking boxes and more about the impact you create. You’ll use your skills and judgment to take ownership of meaningful work, improve how we operate, and help move Kin’s mission forward. Along the way, you’ll deliver outcomes that make a real difference for both Kinfolk and the homeowners we serve.

By the end of your first year, you should feel confident in your role, trusted as an owner, and proud of the progress you’ve helped make.

  • Training programs across Operations are delivered consistently with strong engagement and measurable learning outcomes such as ≥ 90% employee retention rate, ≥ 85% knowledge check pass rate on first attempt, and < 5% major error rate in nesting
  • Facilitators are performing at a high level, receiving strong coaching, and continuously improving their facilitation skills, resulting in ≥ 4.2 / 5.0 training delivery scores from peers and managers, and ≥ 4.0 / 5.0 learner satisfaction scores in post-training surveys
  • Newly trained team members ramp faster and demonstrate improved readiness and operational performance, with a goal of floor readiness ≤ 45 days post training
  • Strong partnerships are established with Operations leaders, resulting in proactive identification and resolution of learning gaps
What you’ll bring
  • 5+ years of experience in training, learning and development, operations enablement, or a related field
  • 2+ years of experience in a leadership role with…
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