Health Insurance Jobs in Fairfield, CT (NOW HIRING)

THE OPPORTUNITY & WHAT YOU'LL DO

This is a service-first role centered mostly around protecting and serving our existing book of business. Your main job is to ensure our current clients never feel forgotten or transactional.

• Primary Client Management: Be the primary daily point of contact for our established Medicare, ACA, and Group clients, helping them navigate complex plan designs and carrier networks.
• Retention & Renewal Operations: Manage renewals, plan changes, and inbound client service tickets with incredible care, speed, and regulatory precision.
• Systems & Data Tracking: Utilize our CRM and quoting platforms to flawlessly document client histories and track account health.
• Maintain the Strategic Priority: Your core focus remains the preservation and exceptional care of our existing accounts. While you will be fully compensated for any natural expansion or inbound referrals that come your way, new client acquisition is a secondary perk and must never come at the expense of our daily service standard.

WHAT WE OFFER  

​We believe in building an environment where people can do their best work. That means providing a competitive financial foundation, clear avenues for professional growth, and the structure you need to feel supported in areas of your life. 

• Competitive base Salary
• Health Insurance
• Training milestone bonuses
• Performance Bonuses
• Client referral bonuses
• Training & Learning Bonuses
• Paid time off
• Paid holidays

​​​​WHO YOU ARE & WHAT YOU BRING

Externally, your demeanor is warm, friendly, and dependable.  Internally, you thrive on being sharp, deeply curious, highly organized, you are mission driven, and you are looking to learn how a modern business actually operates.

Required:

• Be authorized to work in the United States without employer sponsorship or employer participation in an immigration-related work authorization process, now or in the future.
• You must possess an Active Connecticut health insurance license in good standing.
• Exceptional written and verbal communication skills; you enjoy interacting with people and have a natural capacity for empathy and kindness.
• An elite organizational mindset. You pay attention to details others miss , love ticking boxes off a checklist, and take pride in precise data management.
• A strong work ethic and a "no task is too small" ownership mentality.
• You're tech-driven by nature. Systems don't intimidate you; with training, you thrive in a cloud-based, paper-light environment.

Preferred (but not required):

• Active health insurance licenses in other states including NY, NJ, MA, SC, GA, and FL.
• Experience: Prior experience in customer-facing roles (hospitality, retail, banking, corporate administration, or healthcare).
• Tools: Familiarity with Google Workspace, Apple hardware/OS, modern CRMs, and foundational AI Models (Gemini, ChatGPT, Claude, etc).
• Languages: Bilingual or multilingual skills (Spanish and/or Portuguese) are a huge asset.

Note: If you believe you’re a fit for this role, but don’t meet our preferred qualifications, we still encourage you to apply. While our hard requirements are non-negotiable, we’re otherwise open-minded, and don’t need you to be the “perfect” candidate on paper

WHERE CAN YOUR CAREER GO?

Successful mastery of this role is a definitive launching pad inside the business. Depending on your performance and interests, your path can evolve directly into:

• Operations & Technology Management: Building and scaling workflows)
• Digital Marketing & Growth Operations: Driving lead generation and branding)
• Licensed Advisory / Client Management: Stepping into a more advance producer or senior advisory track)
• Something else? As you grow, perhaps a completely different role emerges that is best suited to your skillset 

The door is wide open if you're ready to walk through it.

WHAT TO KNOW GOING IN (THE FINE PRINT) 

• Home Office: We currently operate out of a home-based office in a residential area. We are actively scouting a fully dedicated commercial office in the surrounding area and plan to transition in the near future, but for now, this setup is entirely by design. It is lean, quiet, and intentionally structured to support deep work and close collaboration. While the current workspace is located within a residential property, it functions as a completely separate, fully equipped professional environment occupying an entire floor. If you thrive in fast-moving, purpose-driven settings, you'll feel right at home. We realize, however, that this isn't for everyone, and that's okay.
• Chaos: We're a small, growing company, where things move fast, change often, and sometimes feel messy, in the Health Insurance field. You have to be someone who can thrive in ambiguity, solve problems as they come, and stay focused.
• In-person: This role is fully onsite to help you get embedded in our tools, systems, and culture from day one.  You'll be working directly with members of the founding team. That means high access, rapid decisions, and a chance to shape the future. Around here, your independence and ideas are essential. If you're ready to speak up, dive in, and contribute meaningfully, this is your kind of place.

READY TO APPLY ? 

If you like what you've read please submit an application using our online application tool

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Formed in 1988 as a partnership in Connecticut, our company has morphed into The Strategies Group, a Limited Liability Company, in 1996. We are a health insurance agency and active members of the Stratford Chamber of Commerce and the Bridgeport Regional Business Council.

We help you navigate through the various complex processes of selecting the insurance coverage that is the best for you as an individual or for your group. Whether or not you're an Organization or Individual, our goal to help you achieve peace of mind as you negotiate the complicated landscape of health insurance coverage.

Our expansive capabilities stretch across solutions for Companies and Organizations, Individual Solutions, Corporate Wellness, Federal Assistance coverage and more.