Cross-Functional Support Representative

Overview

Are you a highly organized, detail-loving professional who thrives on variety and enjoys supporting a team behind the scenes? We’re looking for a Cross Functional Support Representative to join our fully remote team! In this dynamic role, you’ll support both our sales and service teams through insurer portal data entry, back-shop and billing support, and special projects. You’ll also take the lead on key initiatives like our Cheep Apartment Protection Program (CAPP) and contribute to process improvements that help the whole team work smarter. If you love variety, teamwork, and making an impact, we’d love to hear from you!

Key Accountabilities

• Accurately upload new business, endorsement, and cancellation information into insurance carrier portals and systems, ensuring compliance and turnaround time targets are met.
• Act as backup support for Billing and Back Shop leads during peak times and vacations.
• Manage our Cheep Apartment Protection Program (CAPP), including monthly bulk renewals, landlord partner communication, and service request coordination.
• Handle special projects as assigned — including rollovers, tech tasks, and process improvements.
• Review and action daily reports and pending download bins to ensure accuracy and follow-through.
• Communicate professionally with insurer partners’ underwriting and tech support teams.
• Contribute to team meetings, one-on-ones, and overall team performance goals.
• Support team training by helping with onboarding, virtual training, and job shadowing sessions.
• Maintain up-to-date knowledge of insurer binding authorities, submission procedures, and rating/underwriting changes.
• Understand payment and financing methods (direct bill, agency bill, premium financing) and follow all procedures.

Qualifications and Skills

• Strong attention to detail and a high degree of accuracy in data entry.
• Proficient with computer applications and quick to learn new systems.
• Organized and able to manage time across competing priorities.
• Comfortable working independently and as part of a collaborative team.
• Strong verbal and written communication skills.
• Experience in the insurance industry or with insurer portals is a strong asset.
• Eager to learn and take on increasing responsibility over time.

Compensation

Salary to be determined by education, experience and qualifications.

About Cheep Insurance

Our Mission:

We believe insurance should be simple, convenient, and accessible to everyone.

We help find personal insurance & payment plans that work for everyone – even if you don’t have the best driving record, credit, or payment history.

Our Core Values

Our company culture is very important to us – we’re looking for team members who align with our core values:

• People First – We believe in teamwork, empowerment, empathy, & open communication.
• Innovation & Simplicity – We work smarter, not harder.
• Professionalism – We take pride in our work, act with integrity, and lead with accountability.
• Good Vibes – We strive to bring positive energy to the world of insurance.
• Growth-Focused – We take initiative to #GSD (if you know, you know) and make our vision a reality.

Highlights of Working at Cheep Insurance

• Work from home full time to maximize work-life balance
• Opportunities for growth and development
• Positive work culture and relationships, including a formal employee recognition and appreciation platform
• Simplified workflows to make life as easy as possible for our team (in the insurance broker world, this can be hard to come by!)
• Our fun team culture and fast-paced environment make the work day enjoyable!

Working at the Southampton Financial Group of Companies

Cheep Insurance is a proud member of the Southampton Financial Group of Companies.

Our aim is to create a workforce that is diverse, promotes positivity, and demonstrates the values of equality, fairness, and respect in everything we do. We are dedicated to an antidiscrimination approach and provide equal opportunity for employment regardless of gender, race, ethnicity, national origin, age, sexual orientation or identity, education, or disability. We respect and value diverse life experiences and cultures and ensure that all voices are valued and heard.

Southampton Financial Inc. welcomes and encourages applications from people with disabilities. Accommodations are available on request for candidates taking part in all aspects of the selection process.

Apply Now

Interested? Send your resume and cover letter to [email protected] to apply.

We thank all applicants for their interest; however, only those selected to be interviewed will be contacted.