Operations Training Manager, Delivery

About this role

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.

WHO WE ARE

Kin makes life simpler, more affordable, and better for homeowners — especially in the places where climate risks, rising costs, and outdated systems make it harder. We start with smarter homeowners insurance and expand to everything homeowners need to thrive.

Using data, technology, and thoughtful human support, we’re building products that are clear, fair, and help homeowners feel confident — so homeowners aren’t left behind when they need help most.

Founded in 2016, Kin is a remote-first employer with Kinfolk across more than 35 states. We serve customers in 13 states (and counting). Our disciplined growth, strong customer satisfaction, and focus on long-term sustainability fosters outstanding growth, attracts marquee investors, and earns recognition and accolades, including:

- Built In Chicago's Best Places to Work, Midsize Companies (2021-2026)

- Forbes' America's Best Startup Employers (2021-2024)

- Inc. 5000 Fastest-Growing Private Companies

- Forbes’ Fintech 50 (2025-2026)

- Great Places to Work Certified (2024-2026)

Most importantly, we’re building Kin to be a place where people do meaningful work with real impact — for our customers, our communities, and each other. We're excited to tell you more about how you can contribute to our rapid growth, strong unit economics, profitability, and excellent customer ratings. To learn more about how we work and what we’re building, visit kin.com http://kin.com and see how we work https://www.linkedin.com/company/kin-insurance/life/kin/.

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 direct reports

- The capacity to thrive within a high-speed, evolving landscape while managing ambiguity effectively

- Experience working in a highly regulated industry such as insurance, f

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