Quality & Training Lead, Insurance Operations

Jerry.ai is making insurance as easy as it should be. We’ve built a platform that finds competitive policies in minutes, ensuring our customers have the best coverage at the best price. Our Sales and Service teams are the front line of this mission, and we are looking for a Quality & Training Lead to be the architect of their success.

As the Quality & Training Lead, you aren't just checking boxes—you are building the blueprint for excellence. Reporting to the Senior Manager of Contact Center Operations, you will own the end-to-end strategy for Quality Assurance (QA) and Training across our Sales and Service departments.

You will design the curriculum that turns new hires into experts, build the scorecards that define "great" service, and partner with Legal and Carrier teams to ensure we are always compliant and ahead of the curve.

• Build the Standard: Develop and scale our QA program, including call audits, scorecards, and calibration processes that align with regulatory and carrier standards.

• Educate & Empower: Design and deliver comprehensive training for new hires and ongoing education for veterans, focusing on product knowledge, system proficiency, and sales/service effectiveness.

• Drive Licensing Success: Own the insurance licensing process, providing prep support and tracking to ensure our team is fully credentialed and compliant.

• Analyze & Optimize: Use QA data and performance trends to identify skill gaps and translate them into "just-in-time" training initiatives.

• Knowledge Management: Maintain our internal knowledge base (SOPs, job aids, and e-learning modules) to ensure the team has the most accurate information at their fingertips.

• Collaborate: Partner with Legal, Compliance, and Carrier Relations to operationalize new requirements and product updates.

• An Insurance Pro: You have 3+ years in insurance operations (agency, brokerage, or carrier) and hold an active P&C license (or are willing to obtain one quickly).

• A Natural Coach: You have 2+ years of experience in training, quality auditing, or performance coaching. You love seeing others succeed.

• Analytical & Detail-Oriented: You can look at a spreadsheet of audit scores and see a story. You know how to turn data into a coaching plan.

• Communicator: You can break down complex insurance regulations into clear, actionable guidance for a front-line team.

• Adaptable: You thrive in a fast-paced environment where things change quickly, and you’re comfortable building processes from the ground up.

• Pay: $90k-$120k base salary + equity (stock options)

• Workplace: Remote (we will provide you with equipment)

• Schedule: Monday–Friday, 8:00 am – 4:30 pm EST

• Benefits: Insurance (health, vision, dental), paid time off, paid parental leave, 401K with employer matching, etc.

While we appreciate your interest and application, only applicants under consideration will be contacted.

Jerry.ai is proud to be an Equal Employment Opportunity employer. We prohibit discrimination based on race, religion, color, national origin, sex, pregnancy, reproductive health decisions or related medical conditions, sexual orientation, gender identity, gender expression, age, veteran status, disability, genetic information, or other characteristics protected by applicable local, state or federal laws.

Jerry.ai is committed to providing reasonable accommodations for individuals with disabilities in our job application process. If you need assistance or an accommodation due to a disability, please contact us at [email protected]

The successful candidate’s starting pay will fall within the pay range listed on this job posting, determined based on job-related factors including, but not limited to, skills, experience, qualifications, work location, and market conditions. Ranges are market-dependent and may be modified in the future. In addition to base salary, the compensation may include opportunities for equity grants.

We offer a comprehensive benefits package to regular employees, including health, dental, and vision coverage, paid time off, paid parental leave, 401(K) plan with employer matching, and wellness benefits, among others. Equity opportunities may also be part of your total rewards package. Part-time, contract, or freelance roles may not be eligible for certain benefits.

About Jerry.ai:

Jerry.ai is America’s first and only super app to radically simplify car ownership. We are redefining how people manage owning a car, one of their most expensive and time-consuming assets. 

Backed by artificial intelligence and machine learning, Jerry.ai simplifies and automates owning and maintaining a car while providing personalized services for all car owners' needs. We spend every day innovating and improving our AI-powered app to provide the best possible experience for our customers. From car insurance and financing to maintenance and safety, Jerry.ai does it all.

We are the #1 rated and most downloaded app in our category with a 4.7 star rating in the App Store. We have more than 5 million customers — and we’re just getting started. 

Jerry.ai was founded in 2017 by serial entrepreneurs and has raised more than $240 million in financing.

Join our team and work with passionate, curious and egoless people who love solving real-world problems. Help us build a revolutionary product that’s disrupting a massive market.