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We're Hiring: Retention Specialist — Personal Lines Fully Remote | Full-Time | FirstMark Insurance

June 26, 2026

At FirstMark, we don't treat a renewal as paperwork. We treat it as a promise — the chance, every single year, to show a client that trusting us with what matters most was the right call. We're growing, and we're looking for a Retention Specialist to stand on the front lines of that promise. This is the person our clients remember. The steady voice on the other end of the line who knows their policy, knows their story, and makes sure they always land in the right place for the year ahead. If you love people, know personal lines inside and out, and take real pride in being the reason someone stays — keep reading. WHAT YOU'LL DO<ul><li>Personally review every policy at renewal, side by side with the client, and guide them to the smartest path for their next policy period.</li><li>Know when to keep a client right where they are — and when to re-market their account across our deep bench of carriers to find them something better.</li><li>Own a book of 2,000+ accounts a year, treating each one like it's the only one.</li><li>Partner with our incredible teams to deliver a world-class, boutique client experience in every single interaction.</li></ul> WHO YOU ARE<ul><li>You have at least 2 years of personal lines insurance experience in a client-facing role.</li><li>You're a natural relationship-builder and leader — warm, clear, and genuinely easy to talk to.</li><li>You're organized and proactive, the kind of person who gets ahead of a renewal instead of chasing it.</li><li>You see retention as care, not a quota. Doing right by the client is always the strategy.</li></ul> WHAT WE OFFER<ul><li>A fully remote role — do your best work from wherever you are.</li><li>Health insurance, 401(k), and PTO.</li><li>A genuine Monday–Friday, 8:00 AM–5:00 PM PT schedule.</li><li>A growing company with a boutique heart, where your work is seen, your ideas matter, and the team actually feels like one.</li><li>Salary DOE - $50,000-$55,000 </li></ul> We're building something special at FirstMark — a place where clients feel cared for and team members feel home. If that's the kind of work you've been looking for, we'd love to meet you. Ready to be the reason our clients stay? Apply today, or message us directly. #Hiring #InsuranceJobs #PersonalLines #RemoteJobs #InsuranceCareers #NowHiring

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Common Interview Questions And Answers

1. HOW DO YOU PLAN YOUR DAY?

This is what this question poses: When do you focus and start working seriously? What are the hours you work optimally? Are you a night owl? A morning bird? Remote teams can be made up of people working on different shifts and around the world, so you won't necessarily be stuck in the 9-5 schedule if it's not for you...

2. HOW DO YOU USE THE DIFFERENT COMMUNICATION TOOLS IN DIFFERENT SITUATIONS?

When you're working on a remote team, there's no way to chat in the hallway between meetings or catch up on the latest project during an office carpool. Therefore, virtual communication will be absolutely essential to get your work done...

3. WHAT IS "WORKING REMOTE" REALLY FOR YOU?

Many people want to work remotely because of the flexibility it allows. You can work anywhere and at any time of the day...

4. WHAT DO YOU NEED IN YOUR PHYSICAL WORKSPACE TO SUCCEED IN YOUR WORK?

With this question, companies are looking to see what equipment they may need to provide you with and to verify how aware you are of what remote working could mean for you physically and logistically...

5. HOW DO YOU PROCESS INFORMATION?

Several years ago, I was working in a team to plan a big event. My supervisor made us all work as a team before the big day. One of our activities has been to find out how each of us processes information...

6. HOW DO YOU MANAGE THE CALENDAR AND THE PROGRAM? WHICH APPLICATIONS / SYSTEM DO YOU USE?

Or you may receive even more specific questions, such as: What's on your calendar? Do you plan blocks of time to do certain types of work? Do you have an open calendar that everyone can see?...

7. HOW DO YOU ORGANIZE FILES, LINKS, AND TABS ON YOUR COMPUTER?

Just like your schedule, how you track files and other information is very important. After all, everything is digital!...

8. HOW TO PRIORITIZE WORK?

The day I watched Marie Forleo's film separating the important from the urgent, my life changed. Not all remote jobs start fast, but most of them are...

9. HOW DO YOU PREPARE FOR A MEETING AND PREPARE A MEETING? WHAT DO YOU SEE HAPPENING DURING THE MEETING?

Just as communication is essential when working remotely, so is organization. Because you won't have those opportunities in the elevator or a casual conversation in the lunchroom, you should take advantage of the little time you have in a video or phone conference...

10. HOW DO YOU USE TECHNOLOGY ON A DAILY BASIS, IN YOUR WORK AND FOR YOUR PLEASURE?

This is a great question because it shows your comfort level with technology, which is very important for a remote worker because you will be working with technology over time...