Operations Training Manager, Delivery

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simpler, more affordable, and better for homeowners — especially in the places where climate risks, rising costs, and outdated systems make it harder.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 and see how we work . 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, finance, health care, or other related field Experience managing training programs or learning initiatives across multiple teams or operational functions Proven ability to lead and develop trainers or facilitators in a performance-driven environment Strong facilitation and coaching skills with experience delivering engaging virtual or in-person learning experiences Ability to translate operational needs and performance data into effective learning solutions Strong cross-functional collaboration skills and the ability to partner effectively with business leaders Excellent organizational and program management skills, including experience managing complex training calendars or initiatives How we hire We believe a great hiring experience should be clear, respectful, and human. We’ll accept applications for this position until August 10th, 2026. While our recruiting team uses AI tools for efficiency, resumes are still screened by Kin’s in-house recruiters, and candidate evaluations and hiring decisions are made by recruiters and hiring teams. Rest assured, real people make real decisions. The hiring process and timeline for each role will vary, depending on the position. However, here are some things you can expect from us: Prompt updates and feedback following interviews Interviews with recruiters, hiring managers, and members of teams Skills assessment relevant to the position, if applicable Genuine, thoughtful human interaction at every step How We Support You We offer a comprehensive, competitive benefits program, allowing you to choose the benefits that are best for you and your family, starting on the first day of the month following your start date. Core Benefits Competitive salary and company equity through Restricted Stock Units (RSUs), granted as part of our standard compensation package and based on role and level 401(k) with company match up to 4% of eligible earnings Multiple medical plan options, plus dental and vision coverage Company-funded HSA contributions (based on medical plan selection) Company-paid life insurance and short-term disability Health & Wellbeing A variety of supplemental benefit options, including long-term disability, critical illness, accident, legal, and pet insurance Access to mental health support and confidential counseling resources Flexible PTO for exempt employees (most employees take 15–20 days per year), plus 8 company-observed holidays Paid parental leave, including up to 14 weeks at 100% pay for birthing parents and 8 weeks at 100% pay for non-birthing parents Growth & Development Career mobility and internal growth opportunities across the organization Professional development budgets for certifications, conferences, and learning available, subject to management approval How we work We don’t just hire for skills. We hire for alignment. Kinfolk bring diverse perspectives, but we’re united by a shared set of values that shape how we work and how we show up for each other and our customers. Run through walls, together - Our industry is stuck in the status quo. But Kin is different. We are challengers. Innovators unwavering in our mission to fix insurance for those who need it most. We are changing insurance for good. We roll up our sleeves, take action, and get “impossible” things done every day with grit and teamwork. Raise the bar. Drop the ego - Attitudes are contagious. Every one of us is responsible for creating the culture we want to work in. High performance. Low drama. Always respectful. Like professional sports teams, we win by working in sync. We show up, work hard, and play to each other’s strengths. Act like an owner - We are owners, fully accountable for achieving Kin’s mission. That requires positive, proactive, big-picture thinking well beyond our job descriptions. Ask questions, Take ownership. Do the right thing, even when it‘s hard. Because when Kin thrives, so do you. And so do our customers. Operate lean. Deliver more - We build efficiency into everything we do. Each dollar we save gets reinvested to deliver more to our customers: better pricing, more products, and new innovations. We work smarter by relentlessly prioritizing and using technology, including AI, to multiply our impact. Lean is about focus, not deprivation. Lean isn't a limitation – it's our competitive advantage. Keep asking ‘What if?’ - We value curiosity. To make insurance better for our customers, we experiment. We embrace insights. And we base decisions on data rather than assumptions. We see setbacks as opportunities for growth and are always learning and improving. Both individually and as a company. Where we work We are a remote-first company with offices in Chicago, IL and St. Petersburg, FL where teams can come together for collaboration. For Sales Agents and Customer Service Agents: These roles sit in any of the following 30 states: AL, AZ, CO, FL, ID, IL, IN, KS, KY, MA, MD, ME, MI, MO, MT, NC, NE, NM, NV, NY, OH, OK, PA, SC, TN, TX, UT, VT, VA, WA, and WI. For all other positions, these roles can sit in any of the following 40 states: AL, AR, AZ, CA (exempt only), CO, CT, FL, GA, ID, IL, IN, IA, KS, KY, MA, ME, MD, MI, MN, MO, MT, NC, NE, NJ, NM, NV, NY, OH, OK, OR, PA, SC, SD, TN, TX, UT, VT, VA, WA, and WI. Please only apply if you are able to live and work full-time in one of the states listed above. For remote technical positions located in Canada, we are only able to hire individuals who reside in Ontario. Applicants must be able to live and work full-time in Ontario to be considered. State locations and specifics are subject to change as our hiring requirements shift. EEOC statement Kin is proud to be an Equal Employment Opportunity and Affirmative Action Employer. We don't just accept difference – we honor it, nurture it, and celebrate it. We don’t discriminate based on race, religion, color, national origin, gender (including pregnancy, childbirth, or related medical conditions), sexual orientation, gender identity, gender expression, age, status as a protected veteran, status as an individual with a disability, or other applicable legally protected characteristics. Kin welcomes and encourages applications from people with disabilities. Accommodations are available on request for candidates taking part in all aspects of the selection process. If you require accommodation, please contact us by sending an email to [email protected]