Director, Operations Training

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most, starting with their homes and expanding to all they value, in a world where climate risks, rising costs, and outdated systems leave too many behind.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

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.

• As the Director of Training, your days will be a dynamic mix of strategy, execution, and team leadership. You’ll spend time designing and facilitating onboarding programs rooted in adult learning principles—ensuring that new hires in Sales and Customer Service ramp quickly and confidently. Whether leading live workshops, coordinating high-impact role-plays, or partnering with instructional designers to refresh core content, your focus will always be on delivering training that translates directly into performance.

• You’ll oversee a team of seven, providing direction, coaching, and development to maximize their effectiveness. Your leadership will ensure the team remains agile—able to pivot and deploy resources as business needs shift. In parallel, you’ll drive multiple training projects from concept to delivery, managing timelines, delegating responsibilities, and tracking results across each initiative.

• Beyond team and project execution, you'll own performance measurement—establishing KPIs, analyzing outcomes, and optimizing training programs to close gaps in real time. You’ll 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.

• Finally, you’ll play a key role in building internal alignment. Whether you're consulting with stakeholders on program strategy or shaping a roadmap for future enablement efforts, your impact will be both tactical and strategic. In this role, success is defined by faster onboarding, stronger agent performance, and a company-wide recognition that training is a growth accelerator—not a support function.

• 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 360 a plus.

• Strong project management skills with the ability to manage timelines, resources, and competing priorities

• Exceptional facilitation, communication, and presentation skills

• Proven ability to gather insights from subject matter experts and translating them into effective learning experiences.

• Ability to thrive in a fast-changing environment while maintaining a results focus

• Strong delegation and leadership abilities

• You are comfortable working in moments of ambiguity and changing priorities

• You’re outcome-oriented, as well as collaborative. Taking ownership and prioritizing key outcomes is important, but so is taking an emotionally intelligent approach to working with others. Working with strong-willed people is something you enjoy.

• You wake up positive and driven to improve what’s in your control

• You can quickly assess a large, complex workload and organize it into a clear, structured, and efficient process.

• You are optimistic, energetic and even if people disagree with you, you can hold their attention

• You prefer to follow existing playbooks instead of building and leading your own.

• You’re uncomfortable with shifting priorities, high visibility, or high expectations.

• You see training as content delivery, not a strategic lever tied to sales performance.

• You avoid difficult conversations, delegation, or coaching.

• You want a solo contributor role—this is a team leadership position.

Oh, and don’t worry, we’ve got you covered!

We offer a comprehensive benefits program, allowing you to choose the

benefits that are best for you and your family including: Medical, Dental, Vision, Life Insurance, Short and Long Term Disability Insurance options, Employee Assistance Program, as well as elective voluntary benefits such as accident insurance, hospital indemnity, critical illness, legal assistance, and pet insurance. Kinfolk become eligible for benefits on the first day of the month following their start date.

In addition to these benefits, we also are excited to offer the following:

• Competitive salary and company equity through Restricted Stock Units (RSUs), granted as part of our standard compensation package and based on role and level.

• 401K with company match of up to 4% of eligible earnings

• Flexible PTO for exempt employees (employees typically take 15-20 days annually), along with 8 company-observed holidays

• A paid parental leave program that provides 100% salary continuation of up to 14 weeks for birthing parents and 8 weeks for non-birthing parents

• Continuing education and professional development opportunities

This role is eligible to earn additional compensation annually through participation in our Kin Leadership Incentive Plan.

Kin will accept applications for this role until September 1st, 2025. We will begin reviewing resumes on a rolling basis from now through the deadline, ensuring every applicant who applies by the close date is given full and fair consideration.

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, MN, 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.

State locations and specifics are subject to change as our hiring requirements shift.

Kin is the only pure-play, direct-to-consumer digital insurer focused on the growing home insurance market. We make policies convenient and affordable through a technology platform that delivers a seamless user experience, customized options for coverage, and fast, high-quality claims service. Kin is a fully licensed carrier that offers coverage through its reciprocal exchanges which are owned by its policyholders. To learn more, visit www.kin.com.

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.