Operations Trainer
Kin Insurance
Location
Remote (United States)
Employment Type
Full time
Location Type
Remote
Department
Training
Deadline to Apply
April 13, 2026 at 11:59 PM EDT
Compensation
- $65K – $80K • Offers Equity
The posted range represents the typical compensation range for this role. Actual compensation is determined by multiple factors such as market rates, qualifications, experience, and an evaluation of internal pay equity. Additional benefits are included in the job posting.
Quick Summary
Deliver engaging onboarding and skill development programs that prepare Operations team members to perform confidently, ramp quickly, and deliver exceptional results for Kin’s customers.
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simpler, more affordable, and better for homeowners — especially in the places where climate risks, rising costs, and outdated systems make it harder.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 Trainer to deliver engaging, high-impact learning experiences that prepare Kin’s Operations team members for success in their roles. As Kin continues to grow, strong onboarding and continuous skill development are essential to ensuring our teams can deliver exceptional service and operational performance.
In this role, you’ll facilitate new hire onboarding and ongoing training programs that build knowledge, capability, and confidence across Operations teams. You’ll also serve as a critical voice of the learner—providing feedback, insights, and recommendations that help continuously improve training programs, learning materials, and the overall training experience.
Your responsibilities
Facilitate onboarding programs and new hire training for Operations team members across multiple operational functions
Deliver ongoing learning sessions and skill development programs for tenured employees
Create engaging, inclusive learning environments that promote knowledge retention, participation, and skill development
Assess learner progress through evaluations, coaching, and structured feedback
Provide guidance and support to help learners build the knowledge, behaviors, and confidence needed to succeed in their roles
Identify trends in learner performance and training outcomes to inform improvements to training programs
Share insights and feedback with training leadership to enhance training effectiveness and learner engagement
Partner with instructional designers and knowledge management specialists to ensure training materials remain accurate and effective
Collaborate with Operations leaders and subject matter experts to incorporate operational insights into learning experiences
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 sessions are consistently engaging, well-structured, and receive positive learner feedback
New hires graduate from training with the knowledge, skills, and confidence required to succeed in their roles
Learner feedback and performance insights contribute to measurable improvements in training programs and materials
Strong partnerships are built with instructional design, knowledge management, and Operations stakeholders
What you’ll bring
Active personal lines insurance license
2+ years of experience in training, facilitation, learning and development, operations enablement
Strong facilitation and presentation skills with the ability to engage diverse audiences in virtual or in-person settings
Ability to communicate complex processes and concepts clearly and effectively
Experience coaching learners and providing structured feedback to support skill development
Strong collaboration skills and the ability to work effectively with cross-functional partners
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Strong problem-solving and critical thinking skills to adapt training based on learner needs and feedback
How we hire
We believe a great hiring experience should be clear, respectful, and human. We’ll accept applications for this position until Monday, April 13th at 11:59pm CST.
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
Due to the urgent need of this role we anticipate the following timeline:
Applications Accepted and Reviewed: April 6th - 15th
Recruiter Screens: April 16th - 21st
Hiring Manager Interviews: April 22nd - April 24th
Assessment / Final Rounds: Week of April 27th
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 careers@kin.com
Compensation Range: $65K - $80K