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Legacy Health/Specialists

Vol. 4 — Careers

Work that helps real people make a real decision.

We're hiring licensed agents and support staff who want to do this differently. No quota theater, no sales-floor energy — just the actual work of helping neighbors navigate Medicare.

Scroll to see what we look for
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What you'd do

Roles that make an impact.

The day-to-day is people-first. Here's what that looks like in practice.

Meaningful conversations

You'll spend your day actually helping people figure out a confusing chapter of their life. Not selling, not pressuring — guiding.

Advanced technology

Modern CRM, modern dialer, modern enrollment tools. We invest in the tools that let you focus on people, not paperwork.

Human-centered approach

Our calls are not scripted. Our managers don't fixate on talk time. The work is the work — do it well and the rest follows.

Support that fosters growth

Continuing education paid for. Carrier certifications covered. A clear path from new agent to senior advisor to specialist.

Remote-friendly by design

Remote roles, supported properly.

Half our team works fully remote. The other half is hybrid. Neither group gets a worse experience.

Consistent support

Working remote shouldn't mean working alone. Daily team huddles, async docs for everything, a Slack that actually gets used.

Innovative tools

Same tooling as in-office. Same access, same training, same speed. No second-class remote experience.

Nationwide team culture

Agents from coast to coast. Quarterly virtual gatherings, optional in-person retreats, and a bias toward over-communicating.

Growth without limits

Geography doesn't cap your career. Senior roles are open to anyone who does the work — wherever you happen to live.

Benefits & perks

The practical stuff.

Pay, time off, healthcare, parental leave, and a few other things that matter. No ping-pong tables.

Career opportunities

Clear progression paths and internal mobility — most leadership came up through the agent track.

Competitive compensation

Base salary plus performance bonuses tied to real outcomes, not vanity metrics.

Healthcare benefits

Medical, dental, vision, and mental health coverage. (We sell insurance — yes, we believe in it.)

Incentives & rewards

Quarterly recognition, annual top-performer trips, and meaningful peer-nominated awards.

Generous PTO

Three weeks to start, four weeks at year three. Plus eleven paid holidays. Take the time.

Parental leave

12 weeks paid for primary caregivers, 6 weeks for secondary. Phased return supported.

Open positions

No open roles posted right now.

We hire when we find the right person. If this page resonates with you, send us a note — we keep a short list, and the next opening tends to come from it.

Not what you were looking for?

Maybe you're a client, not a candidate.

If you landed here looking for help with your Medicare plan instead of a job, we'd love to hear from you all the same.