Jerry Technologies Inc. logo

Customer Experience Advocate (Remote, Insurance Tech Startup)

Job Overview

Location

Orlando, Florida

Job Type

Full-time

Category

Customer Support

Date Posted

August 18, 2026

Full Job Description

đź“‹ Description

  • • This job is what Jerry is all about: helping our customers take care of their most important assets, their car and home, with the kind of warmth and speed they didn't expect from an insurance company.
  • • Car and home are people’s most important assets, yet the experience of owning them is stuck in the 90s. Every part of the journey - insurance, repairs, financing, maintenance - is fragmented, complicated, and expensive. Jerry.ai http://Jerry.ai is building the first app to help people manage it all.
  • • The work is fast-paced, high-energy, team-oriented, and fully remote.
  • • A few things our team members love about working at Jerry:
  • • Opportunities to shape the customer experience as the product and services are constantly evolving.
  • • Competitive wage and benefits (medical, dental, vision insurance, 401K match, paid vacation time).
  • • Stock equity (stock options) — we're a tech startup, and you own a piece of what you're building.
  • • Flexible scheduling: a 5-day, 8-hour or a 4-day, 10-hour work week.
  • • Fully remote, with work equipment provided.
  • • A career path in one of the largest industries in the world — insurance. We pay for your P&C insurance license if you don’t have one yet.
  • • And, importantly, the colleagues you work alongside. Ask our team what they value most and the answer is almost always the same: the people and the culture. Jerry is full of people who take their work seriously and take helping each other just as seriously.
  • • This role runs on two paths (sales and service). You don't have to know yet whether you're a sales person or a service person. We will figure this out together through the interview process.
  • • As a member in the Customer Operations team, some of your responsibilities could include:
  • • Taking great care of our customers. Our team members don't just answer the question asked — they catch the thing the customer didn't know to ask about. A coverage gap. A discount they qualify for. A renewal about to spike.
  • • Answering inbound calls from customers shopping auto, home, motorcycle, and other policies, and from policyholders who need something changed.
  • • Getting deep on the product. With a large panel of insurance companies to work from, knowing which one fits which customer is the craft of this job. Our app evolves constantly too, and knowing it inside out makes you the person customers trust to navigate it.
  • • Problem solving to remove barriers between a customer and the right coverage.
  • • Processing service requests — vehicles, drivers, lienholders, policy documents.
  • • Making the product better. Tell us what you're hearing. The feedback loop here is short enough that you'll see your suggestions ship.
  • • Who you are:
  • • Prior work experience in customer service, sales, or hospitality is a plus, but not required
  • • Genuinely friendly and positive attitude and willingness to work as a team
  • • Strong work ethic
  • • Strong problem solving skills
  • • Strong communication skills
  • • Compensation and perks:
  • • For sales path: Hourly wage of $19.00 - 21.00 plus uncapped commissions *Our most successful team members typically earn $100,000+ per year.

🎯 Requirements

  • • Prior work experience in customer service, sales, or hospitality is a plus, but not required
  • • Genuinely friendly and positive attitude and willingness to work as a team
  • • Strong work ethic
  • • Strong problem solving skills
  • • Strong communication skills

🏖️ Benefits

  • • Competitive wage and benefits (medical, dental, vision insurance, 401K match, paid vacation time)
  • • Stock equity (stock options) — we're a tech startup, and you own a piece of what you're building
  • • Flexible scheduling: a 5-day, 8-hour or a 4-day, 10-hour work week
  • • Fully remote, with work equipment provided
  • • A career path in one of the largest industries in the world — insurance. We pay for your P&C insurance license if you don’t have one yet

Skills & Technologies

Remote

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Jerry Technologies Inc. logo
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About Jerry Technologies Inc.

Jerry Technologies offers a mobile-first AI platform that automatically compares insurance quotes, refinances auto loans, and shops for home and renters coverage. Users submit photos of existing policies, and the app retrieves and compares rates from carriers to find lower premiums or better terms. The company earns commissions from insurers when policies are switched or originated through its platform, serving consumers seeking to reduce recurring auto and home expenses without manual comparison shopping.

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