Founding Quote Quality Specialist, Insurance VA (Future VA Team Lead)

About Upline
Independent insurance agents are the backbone of their communities, and most of them are stretched too thin to talk with every customer at renewal. Upline exists to change that. We're the proactive account management platform for independent insurance agents, built to help agencies reach their entire book and defend the relationships they've spent years earning.
Our AI does the heavy lifting behind the scenes. Now we're hiring the person who makes sure every result is right.
Please read first: this is an overseas VA role
This position is built for experienced virtual assistants working from outside the United States. Wherever you are in the world, if you have strong insurance VA experience, we want to hear from you. Compensation is set for the overseas VA market. If you are looking for U.S.-based pay, this role will not be a fit, and we ask that you not apply.
The role
Great technology still needs a sharp human eye. As our first Quote Quality Specialist, you'll be the final check between our platform and the agencies we serve. You'll learn the ins and outs of how independent agencies work: quoting, shopping carriers at renewal, and communicating with customers. You'll know a good quote when you see one, catch a bad one fast, and step in to run it yourself when it needs a human hand.
Then you'll help build what comes next. As Upline grows, you'll set our quality standards, train the specialists who join after you, and lead our VA team. We're looking for a long-term partner.
What you'll do first
Review personal-lines quotes (auto and homeowners) for accuracy against carrier rules and each agency's preferences
Verify coverages, limits, deductibles, and property details before anything reaches an agency
Run quotes manually in carrier portals whenever a quote needs a human touch
Communicate with agency customers clearly, warmly, and professionally
Know when to approve, when to verify, and when to escalate, and find missing details from outside sources like property records
Flag patterns, carrier quirks, and exceptions so our system keeps getting smarter
Where this goes
Turn what you've learned into quality standards, SOPs, and training
Become the go-to person for quality and process questions
Lead and grow the Upline VA team
Help shape how our people and our AI work together
What you bring
2+ years in insurance quoting or agency support, with hands-on carrier portal experience (Progressive, Travelers, Nationwide, Safeco, Liberty Mutual, and similar)
The ability to run a personal-lines quote manually, start to finish
Solid personal-lines knowledge: coverages, limits, deductibles, and endorsements, and the ability to explain them in plain English
Experience shopping auto and home policies or working renewals
Strong written and spoken English and a customer-first way of communicating
Serious attention to detail. "Close enough" doesn't work for you either.
A basic working understanding of AI tools and large language models (LLMs), plus the curiosity to keep learning
Comfortable working remotely with a U.S.-based team, with 2 to 4 hours of overlap with U.S. Central Time
Big advantages
You already use Claude (Anthropic's AI assistant) in your work
You've reviewed or audited other people's insurance work (QC, QA, or team lead)
Agency management systems like EZLynx, HawkSoft, AMS360, or Applied Epic
You've trained other VAs or written process documentation
Property research tools like Zillow, Redfin, or replacement cost estimators
Why Upline
Ground floor of a new company, working directly with the founders
Paid training and real, regular feedback
A clear path from first hire to VA team lead
Monday to Friday schedule with fixed weekends off
Paid holidays and PTO, plus internet, equipment, and health stipends
How to apply
Apply here and include:
A link to a 2 to 4 minute video (put it at the top of your resume): your experience, and why you want to build this with us
Your resume, plus every carrier portal, AMS, and rater you've used
Your availability in U.S. Central Time
One real example of how you've used Claude or another AI tool to do your work better

Work arrangement
Yes