Medicare Advisor-Mesa/Remote

| Remote
Employer Provided Salary: $52,000 Annually
Salary data is provided by the employer. Please note this is not a guarantee of compensation.
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Why We Exist

Every morning, 11,000 Americans wake up and begin their first day of retirement. While retirement should be an exciting, empowering, and fulfilling part of one’s life, the reality today is that retirement brings along with it a fundamentally new set of challenges that make it an overwhelming time for many.
At Chapter, we believe that the current infrastructure for retirement is broken, and we’re on a mission to fix it. We’ve started by building industry leading technology to solve the first major obstacle in retirement: navigating Medicare (healthcare coverage for retirees over 65). Our products help seniors sign up, choose an insurance plan, and leverage their plan after they are enrolled. And, unlike most Medicare advisors who only search plans that pay them, Chapter searches every Medicare option nationwide. This allows us to find savings and benefits that others miss.
But our ambition doesn’t stop with Medicare — we seek to transform the way that Americans navigate and experience retirement. If this sounds exciting to you, we’d love to speak with you.

Our Commitment

Chapter provides the best Medicare guidance in America by breaking down barriers to information, training best-in-class Advisors, and maintaining continuous community & support.
Other advisors only recommend plans from insurance companies that pay them. Chapter’s technology enables its Advisors to search every plan from every carrier at unprecedented levels of detail—to ensure we provide the best recommendation every time.
Every Chapter Advisor is trained to use our proven 3 Ps Method to review each Medicare beneficiary’s providers, prescriptions, and priorities—ensuring that every client receives the high-quality healthcare they need and deserve at the best value.
We never stop being there for our members and provide continuous community & support to ensure no one’s ever left alone in this exciting chapter of life!

How You’ll Contribute to our Mission

Chapter is looking to expand our advisory team. In this role, we impact lives daily by saving our members thousands on out-of-pocket medical costs and insuring financial stability in what should be the best chapter of their lives. As a medicare expert, you will listen, guide, teach and empathize with our members in their medicare Journey. Our advisors offer concierge-level service with our proprietary technology to guide Retirees into the top coverage for them this year and every year after. This is a full-time role. We are currently offering a $1,500 signing bonus *to all new Medicare Advisors* *who start before April 1st, 2024
In this role, you will spend several hours each day advising seniors via phone and email.
You should apply for this position if you are excited to set and achieve ambitious goals. We measure advisor performance based on three things:
1) Customer satisfaction
2) Customer retention
3) Number of customers enrolled
While your compensation will be tied to your performance, it does not vary based on the specific coverage you recommend, even if it is with a carrier that does not pay Chapter.

What You'll Do

  • Assess seniors’ Medicare needs with an engaging, natural, and professional demeanor.
  • Provide prompt and efficient service by phone and email.
  • Use Chapter’s software to identify plan options for seniors.
  • Demonstrate strong prioritization skills to determine what is important.
  • Educate & guide clients into the right insurance coverage for them

About You

  • Strong sense of ownership, self-motivated, driven, and able to work independently as well as fostering a collaborative environment
  • Active life and health license or desire to train and become a licensed insurance agent
  • Computer savvy
  • Strong interpersonal skills and distinguished verbal and written communication ability
  • 2+ years of prior Medicare sales experience

Benefits and Perks

  • Full medical, dental, and vision premiums covered at 100% for full-time employees
  • Partnerships with Talkspace (mental health support), Teledoc (telehealth), and OneMedical (concierge medicine)
  • Wellness & Home office stipend
  • In-office lunch and a stocked office pantry
  • Join a BuiltIn NYC startup to watch in 2022
  • Generous parental leave
  • Paid holidays (10 days of PTO, 5 sick days, & 5 Bonus PTO days after AEP)

The salary for this role will be the $52,000/$25.00 an hour, with uncapped commission structure (OTE 80,000 - 140,000) + equity, but it might vary depending on skills and experiences. If you think you'd be a good fit for the role, you should apply. All of our offers are based on our assessment of each individual's unique skills and experience.

Our Commitment

Chapter embraces diversity and equal opportunity in a serious way. We are committed to building a team that represents a variety of backgrounds, perspectives, and skills. The more inclusive we are, the better our work will be.

Chapter will provide any necessary accommodation during the recruitment and selection process to an employee or applicant with a disability. 

If you have a disability or special need that requires accommodation at any time during the recruitment process, please let us know.

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Technology we use

  • Engineering
    • JavascriptLanguages
    • PythonLanguages
    • TypeScriptLanguages
    • GCSLanguages
    • Next.jsLanguages


We're centrally located in NoHo, right next to NYU's campus and easily accessible by subway.

An Insider's view of Chapter

What are some social events your company does?

In addition to doing happy hours almost every month, Chapter's Culture Council also plans other fun excursions like escape rooms, baseball games, paint & sips, and more. We do team lunches at local restaurants and host a holiday party every December with plus-ones.


Enterprise Marketing Manager

What's the biggest problem your team is solving?

As our organization continues to grow, my team is currently focused on how our cross-functional prioritization will be determined & communicated to our internal stakeholders.
Ruthless prioritization is essential for a growing startup and we must ensure that all of our teams work together in that approach as we continue to build & solve new problems


Senior People Partner

What unique initiatives do you have that encourage innovation?

If you rely on the CEO to spur innovation, you’ve already lost. We hire amazing people who have excellent ideas, and we give them support to build.



What does your typical day look like?

A typical day might include building a new KPI dashboard, running trainings for our advisor team, brainstorming retention strategy, or any of the many day to day activities that go into “keeping the ship afloat” at a startup. The variety of work our team takes on has helped me continue to learn and grow in my role at Chapter.


Senior Operations Associate

What are Chapter Perks + Benefits

Partners with nonprofits
Open door policy
OKR operational model
Team based strategic planning
Open office floor plan
Employee-led culture committees
Hybrid work model
Employee awards
Flexible work schedule
Remote work program
Mandated unconscious bias training
Health Insurance & Wellness Benefits
Flexible Spending Account (FSA)
Dental insurance
Vision insurance
Health insurance
Wellness programs
Mental health benefits
Financial & Retirement
Company equity
Child Care & Parental Leave Benefits
Generous parental leave
Return-to-work program post parental leave
Fertility benefits
Vacation & Time Off Benefits
Unlimited vacation policy
Generous PTO
Paid holidays
Paid sick days
Flexible time off
Bereavement leave benefits
Company-wide vacation
Office Perks
Commuter benefits
Company-sponsored outings
Free snacks and drinks
Some meals provided
Company-sponsored happy hours
Pet friendly
Fitness stipend
Home-office stipend for remote employees
Professional Development Benefits
Lunch and learns
Promote from within
Continuing education available during work hours

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