Work at a Portfolio Company

Benefits Advisor -Seattle



Accounting & Finance
Posted on Wednesday, May 3, 2023

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:

  • Impact lives daily by guiding older Americans through their Medicare journey and ensuring financial stability in what should be the best chapter of their lives.
  • Listen, guide, teach, and empathize with members to offer concierge-level service with our proprietary technology.
  • Spend several hours each day advising older Americans via phone and email.
  • Set and achieve ambitious goals to measure advisor performance based on customer satisfaction, retention, and enrollment.
  • We value your expertise and commitment to our clients. Our compensation is tied solely to your success in finding the best coverage for them, regardless of which carriers pay us.

Why Choose Chapter:

  • You don't have to be a cold-calling machine! Our marketing partnerships with GoodRx, NerdWallet, dialysis clinics, and Kroger (just to name a few) means that the leads come to you.
  • Join a winning team! Our 5-star reviews from over 800 satisfied clients, with a retention rate of 95%, prove that we're committed to excellence in customer service.
  • Be part of something big! Our mission is to revolutionize the way Americans experience retirement, and you'll be an essential part of making that happen.
  • Tech-savvy? You'll love working with our cutting-edge software and proprietary technology to help older Americans find the best Medicare coverage.
  • Opportunity for growth! With a $100 billion company on the horizon, there's no telling how far you can go with us.
  • This full-time remote role comes with a $1,500 signing bonus for all new Medicare Advisors who start before May 30th, 2023

How We Prepare You:

  • Chapter University: a 6-week program for insurance professionals to master Medicare, our advanced proprietary CRM, and persuasive sales method. Our expert-led curriculum provides deep insights into Medicare, equipping participants to offer personalized solutions and stay ahead of industry trends.
  • All licensing expenses covered, paving the way for success
  • Maximize your potential with our unparalleled support and resources

About You:

  • You're a Medicare expert with a proven track record of success and at least one year of experience.
  • You're driven, self-motivated, and take ownership of your work.
  • You have outstanding collaboration and interpersonal skills, with exceptional verbal and written communication.
  • You're highly motivated to succeed and have a strong sense of accountability for your goals.
  • You're a resilient self-starter who thrives in a fast-paced environment.


  • Enjoy full coverage for medical, dental, and vision premiums as a full-time employee – no need to worry about unexpected healthcare costs!
  • Benefit from our partnerships with Talkspace (mental health support), Teledoc (telehealth), and OneMedical (concierge medicine) to prioritize your well-being.
  • Get a wellness and home office stipend to help you create a comfortable and productive work environment.
  • Join an exciting BuiltIn NYC startup that's taking the industry by storm – be a part of something big!
  • Take advantage of generous parental leave to make sure you can balance work and family life.
  • Enjoy paid holidays, including 10 days of PTO, 5 sick days, and 5 Bonus PTO days after AEP – take the time you need to recharge and come back ready to tackle new challenges!

The salary for this role will be $52,000/$25.00 an hour, with an uncapped commission structure (OTE 80,000 - 120,000) + 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.