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 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.

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.

APPLY HERE: Insurance Sales & Service Associate (Remote, Tech Startup)

As a Customer Experience Representative (Advanced Support), you will be the front line of our business, supporting customers through time-sensitive and often sensitive situations while collaborating across teams to ensure safe and reliable service.

We’re looking for adaptable problem-solvers who thrive in a fast-paced environment and are comfortable working schedules that include weekend coverage. Assigned schedules are provided in advance and may vary based on operational needs.

If you enjoy helping customers through complex situations, working with multiple teams, and making a meaningful impact every day, we’d love to hear from you.

Why Join Us?

Culture

Join a supportive and inclusive work environment where collaboration, respect, and open communication are at the core of everything we do.

Competitive Compensation

We offer competitive compensation that recognizes your skills, experience, and contributions.

Flexibility

Work a structured full-time schedule with shifts assigned in advance. As part of a customer-focused operations team, you’ll help ensure coverage across weekdays and weekends.

Technology

Use modern systems and tools that empower you to provide exceptional customer support and continuously develop your skills.

Growth Opportunity

Gain valuable experience in a dynamic customer support environment while collaborating with cross-functional teams across the business.

Safety Focused

Safety is at the heart of everything we do. Our 24/7 safety-first mindset supports both our customers and employees.

What You’ll Do

• Act as the primary point of contact for customer inquiries, including urgent and safety-related concerns.
• Navigate multiple systems in real time to assess situations, prioritize needs, and make informed decisions.
• Collaborate closely with dispatch, field teams, and internal partners to coordinate timely service.
• Build trust quickly through clear, empathetic communication and confident problem-solving.
• Manage complex customer requests involving billing, payments, and service coordination.
• Maintain accurate and detailed documentation across multiple platforms.

 What You Bring

• Proven ability to solve problems in fast-paced, high-stakes environments.
• Strong collaboration skills and experience working across multiple teams.
• Advanced computer proficiency and the ability to multitask across systems.
• Ability to quickly build rapport and manage sensitive customer conversations professionally.
• High attention to detail, sound judgment, and adaptability.
• Availability to work assigned schedules that include weekend coverage.
• Availability to work shifts scheduled between 6:00 a.m. and 6:00 p.m.
• Legal authorization to work in the country where you are applying. We do not sponsor employment visas for this position now or in the future.
• Fluency in Spanish is considered an asset.

Schedule Requirements

• Full-time remote position.
• Weekend availability is required.
• Assigned schedules may include:
  • Wednesday to Sunday
  • Friday to Tuesday
  • Saturday to Wednesday
  • Other similar five-day rotations based on operational requirements
• Schedules are communicated in advance and may change based on business needs.

What Sets This Role Apart

• 1-year contract opportunity.
• Remote work environment.
• Exposure to multiple areas of the business.
• Meaningful work that directly supports customer safety and service excellence.
• A collaborative team environment focused on problem-solving and continuous improvement.
• The opportunity to make a real impact during critical customer interactions.

The expected hourly range for this role is $18.00-$22.50 per hour.

Please note that compensation information is provided as a general guideline only. Actual compensation will be determined based on skills, experience, qualifications, market conditions, and geographic location.

APPLY HERE: Customer Experience Representative (Advanced Support)

Live in Arizona, Florida, New York, South Carolina, or Texas? Join a Top Workplace!

Looking for a temporary remote opportunity with the potential to grow into something more?

Velocitii is hiring Remote Underwriting Processors for a contract assignment running from 9/21/2026-1/31/2027. In this role, you’ll play a key part in the underwriting process by reviewing applications, verifying documentation, and ensuring accuracy and compliance for health insurance policies.

This is a temporary contract position, with the potential to be considered for a regular full-time position at the completion of the contract based on business needs and performance.

WHAT’S IN IT FOR YOU – THE PERKS! 

💵 Compensation & Contraction Completion Bonus

• Pay is dependent on state:
  • AZ/NY: $17.00/hour
  • FL/SC/TX: $16.00/hour
• Paid training provided
• Contract runs 9/21/2026-1/31/2027
• Completion bonus available at the end of the contract based on certain qualifications

💻 Company-Provided Equipment

• We’ll set you up with everything you need to succeed—no equipment worries!

🏠 Remote Work

• Work comfortably from home and skip the commute.

🤝 Supportive Culture

• Velocitii values open communication, compassion, collaboration, and creating a strong sense of belonging for all employees.

📈 Opportunity for Future Employment

• While this position is a temporary contract role, successful employees may be considered for future regular full-time opportunities based on performance and business needs.

🕗 Consistent Schedule

• Monday–Friday 8:30 AM to 5:00 PM EST—no weekends!

A DAY IN THE LIFE

As an Underwriting Processor, you’ll play a critical role in helping ensure health insurance applications are accurate, complete, and compliant. You’ll work closely with agents and team members to gather documentation, review case information, and support underwriting decisions.

You’ll:

• Retrieve and review cases from client systems
• Compare application details against system data to ensure accuracy
• Identify required documentation and request missing information from agents
• Review submitted documents for completeness and compliance with product requirements
• Verify information and escalate discrepancies when appropriate
• Maintain detailed and accurate case records
• Work across multiple systems while managing a high-volume workload
• Collaborate with teammates and leadership to achieve departmental goals
• Meet productivity and quality standards in a fast-paced environment
• End your day knowing you’ve helped ensure accurate processing of health insurance applications

WHAT WE’RE LOOKING FOR

Required:

• Strong verbal and written communication skills 
• Organizational and time management skills
• Critical thinking and problem-solving abilities
• Strong attention to detail and accuracy
• Ability to navigate multiple computer systems 
• Experience in a virtual desktop environment 
• Distraction-free remote workspace 
• High school diploma or GED

Preferred:

• Associates degree or higher
• Previous underwriting, insurance processing, administrative, or related experience
• Experience reviewing documentation for accuracy and compliance
• Healthcare, medical insurance, financial services, or insurance industry experience
• Familiarity with underwriting platforms such a Agenium
• Prior remote work experience

Additional expectations:

• Participate in virtual interviews using a computer with a working camera 
• Comfortable in a diverse, inclusive, team-focused culture 
• Complete pre-employment steps:
  • Internet speed test
  • Background screening, employment verification, and drug screening

APPLY HERE: Medical Insurance Application Processor