Join our team and help us reimagine the retirement experience.

Hi! We’re CoverRight

CoverRight is a digital Medicare concierge. Our mission is to help the 10,000 people retiring everyday find, select and enroll in the right insurance plan.   We do this by making it easy for them to understand their options, compare quotes, and enroll a plan, all in one place. 


We’re growing fast and looking for people with passion, collaborative attitudes, and creative problem-solving skills to join our team.

Open Roles

Sales Manager (Medicare) (NYC / Remote)

CoverRight is an insurance technology (‘insurtech’) startup on a mission to make Medicare more accessible to the 60 million Medicare beneficiaries across the country. We help the 10,000 people retiring every day make one the most complex but important decisions as they age into retirement – finding the right health insurance.

We’re backed by reputable venture capital investors and have assembled a passionate and driven team to tackle an industry long overlooked by technology.  Our mission is to become the most trusted partner in navigating the early-stages of retirement. 

Our team is tight-knit, scrappy, and adaptable to many different roles. We move fast, take risks, and get things done. And, most importantly, we care deeply about each other and our customers.

About the Sales Manager (Medicare) role

CoverRight is looking for a Sales Manager who is excited to take on the responsibility of being the critical driving force behind our early growth story.

You will be the foundational member of our Medicare Sales team will own and manage the Sales Operations of CoverRight end-to-end, with goal of helping us build a multi-tiered sales team. You will be expected to be accountable for performance, reporting, developing strong leaders, and building processes that scale with the business.

You should be an experienced sales leader who can recruit, motivate and coach our Medicare insurance sales staff and develop them as leaders. Above all, your contagious passion for sales stems from helping the customers and the company to succeed.  Your role will include providing observations and suggestions to our Product & Engineering team on how technology can help improve sales efficiency/productivity.

You will report directly to CoverRight’s CEO and be expected to provide input on strategic and tactical decisions around CoverRight’s sales operations, sales processes and sales incentives.


In this role, you will…

  • Work with the CEO to set sales team KPIs and daily, weekly, and monthly targets; drive execution in line with those metrics
  • Develop, maintain, and iterate on sales incentive programs
  • Proactively identify and problem-solve issues related to lead conversion, lead quality, team capacity and service levels
  • Provide timely and accurate executive-level reports of sales performance and forecasts of org needs
  • Own all aspects of people leadership and success in the inside sales org: recruiting, onboarding/training/continuing ed, licensing, performance management, compensation, career development, team structuring, staffing forecasting, scheduling/timekeeping, day-to-day tactical coaching and mentoring
  • Lead by example and ‘roll up your sleeves’ to help with sales and answering customer questions if required
  • A/B test and optimize scripts, contact strategies, team structures, workflows, etc. to drive results and continuous improvement
  • Working collaboratively with other operations leaders including the Product & Engineering team to build technology that will help improve sales productivity and efficiency


We’d love to hear from you if…

  • You have a proven track record of individual sales achievement and sales team leadership; minimum 5+ years of senior-level sales experience, with multi-level leadership experience
  • You are a licensed Medicare sales agent yourself or have been in the past 2-3 years OR have been in a similar role at another fintech/insurtech
  • You understand the importance of data in sales – you know how to stand up a dashboard, what the data means, and can derive insights to determine action
  • Understanding of the market and competitive landscape in which the company operates and ability to use that to shape sales scripts and training
  • You have demonstrated experience building a team from the ground up, including a track record of developing leaders
  • Strong sales mindset and client problem-solving orientation
  • You have a keen eye for detail and “no task is too small” attitude
  • Skilled at building trust with direct reports, peers and leadership but also able to have difficult conversations successfully
Medicare Sales Associate - (NYC / Remote) is looking for a driven licensed health insurance agent to be an early member our Client Success team.  You will be working closely with the Company’s COO to serve our inbound customers while also helping to develop, build and scale CoverRight’s sales function.


This role will give you the opportunity to accelerate your career as our business goes from strength to strength. You’ll be joining a small team at the ground level with unparalleled frontline experience with significant growth opportunities for anyone who demonstrates a high level of competency in their assigned roles. is an insurance technology (‘Insurtech’) startup on a mission to make Medicare more accessible to the 60 million Medicare beneficiaries across the country. We are backed by venture capital investors and have assembled a passionate and driven team to help make Medicare easy for consumers using technology. 


We’d love to hear from you if you:

  • Like the start-up energy and want first-hand experience working at an ambitious startup looking to make a difference

  • Enjoy working in a fast-paced environment and thrive on autonomy

  • Desire a flat structure and direct day-to-day to access senior leadership

  • Are ambitious and not afraid to take on ‘non-traditional’ tasks in order to help scale our platform

  • Like meritocracy – we promote based on performance, not tenure


In this role, you will…

  • Get on the phone and serve as the key point of contact for prospective customers

  • Be a subject matter expert on Medicare for our clients, including complex situations

  • Use a consultative sales approach to guide customers through the application process

  • Demystify the industry jargon and make Medicare easy to understand

  • Work closely with CoverRight’s COO and have the opportunity to have a hands-on approach in setting up the company’s sales function at it scales

  • Collaborate with technology and other teams to ensure both a seamless customer experience and improve our agent-facing technology

  • Continuously improve your performance in a metrics-driven environment, directly impacting your earnings


Apply if you have:

  • 2-3 years of Medicare (Medicare Advantage, Medigap, PDP) sales experience

  • Bachelor’s degree (preferred)

  • Current AHIP certification

  • State licenses in AZ, CA, FL, GA, IL, IN, MO, NC, NJ, NY, NV, OH, PA, SC, TN, TX, VA (must have at least 5 from this list or can quickly obtain)

  • History of compliant insurance sales practices



  • High commissions and production bonuses

  • Opportunity to accelerate career trajectory in a fast-growth start-up

  • Sell the best, national Medicare Advantage / Medigap carriers such as UnitedHealthcare, Humana, Aetna, Anthem, Wellcare, and Cigna more

  • Potential to be remote – sell from the comfort of home so you can be near family

Junior Medicare Sales Associate (NYC / Remote)

CoverRight’s Client Success team provides critical support and services to CoverRight’s new and existing customers.


Our Client Success team thrives on collaboration, creative competitions and thoughtful communication with customers as we drive a positive, tech-enhanced experience in an industry typically known for being ‘old-school’ and paper-based. 


This role is part-time and remote. Successful candidates will have the opportunity to transition into a full-time W-2 sales role with attractive salary + commission compensation package based on performance. We will support your training and licensing needs and requirements.


Your Responsibility

  • Get on the phone and chat to serve as the first point of contact for prospective customers and deliver high-quality customer service

  • Use a consultative approach to help customers demystify the industry jargon, and make health insurance easy to understand plus check if they are eligible for Medicare and Medicare benefits 

  • Work closely with seniors sales teammates to solve complex client problems 

  • Continuously improve your performance in a metrics-driven environment, with potential to directly impacting earnings

  • Ensure prospective customers receive unparalleled service


We’d love to hear from you if… 

  • You are self-motivated, ambitious, and excited to start your career in sales

  • You have experience in a high-volume, fast paced role, bonus points if you have prior experience in a dialer-based role, the insurance industry, or in sales!

  • You’re eager to find yourself among a diverse group of competitive peers, always learning from each other

  • You have a will to succeed in a target-driven environment, with substantial incentives based on various KPIs

  • You work well with others, solving problems on the fly using Slack, Zoom, Google Hangouts and other communication methods

  • Your family and friends would describe you as a natural conversationalist – you keep the conversation flowing and are a pleasure for our clients to speak to!

  • You welcome any and all feedback – you’re looking to improve your skills, and recognize the value of hands-on managers who care deeply about your growth

  • You are open to working some weekends and evenings – since we’re all remote for now these shifts would be from the comfort of your home!

  • You appreciate the value of a well-placed gif!


Desired Attributes:

  • Previous experience in a sales or customer service role, solving customer inquiries and requests (ideally 1+ years experience)

  • Provide availability with flexible schedule

  • Access to high-speed internet – as a startup, we use cloud-based software