Chief Of Staff

United States
Jul 29, 2021
Apply HereContact Recruiter
Apply before: 
Jan 25, 2022

Who are we?

EasyHealth is a tech enabled health marketplace and a leader in the InsureTech space.

We’re reinventing the Medicare insurance member experience, making it easier to buy, sell and use.

We use technology in simple, scalable ways, to make big differences in the member experience.

We are member obsessed and we’re on a mission to improve health options and outcomes for 60 million Medicare-eligible Americans.

We’re looking for talented people that share our vision and we’re excited to build something big and to do it with people that teach and challenge us

Quick Facts About EasyHealth

  • Founded: March 2020
  • Mission:  To create better health outcomes for seniors
  • Vision: Build the first modern Medicare platform
  • Traction: Projecting a $100M+ run rate in 2022. One of the fastest growing insure-tech start-ups ever.
  • Key investors: QED Investors, Anthemis, Healthy VC, Nationwide Insurance
  • Team size: 100+ full-time equivalents (May 2021) and targeting 400+ by end of 2020
  • Location: 100% remote (US required, preferably West Coast/Los Angeles)


  • Extreme Ownership – We fulfill our promises to each other and to our customers. We own our responsibilities 110%.
  • Speed – We work quickly and pragmatically.
  • Positivity – We focus on the potential in the world and in each other. We rise to challenges rather than complain about them. We see a cup half full instead of half empty.
  • Learners - Put your ego aside and learn. This is hard but a worthy pursuit. We’re always striving for better. Helpers - We want to impact people’s lives. Both our customers, our friends and loved ones, and our coworkers. We believe, being a helper at work improves all aspect of life.

Mission of the Chief of Staff to the CEO

The Chief of Staff and his or her team will exercise manager-level “business generalist” capabilities to deliver strategic and tactical execution across all departments.

The Chief of Staff will support the CEO on the most critical projects ranging from strategy, fundraising, and scaling as we grow to 1,000 employees and a category leader within 2 years.

Range of activities will include:

Projects that involve many functions

  • E.g. stewarding OKRs, preparing exec offsite, board meetings, fundraising slides

Projects that are important but are under resourced

  • E.g. designing interviews for a new exec hires; sourcing for our advisory board

Projects that are too early, broad, or nebulous to allocate to a functional owner

  • E.g. exploration of M&A opportunities


This role would be expected to last 12-24 months, after which the Chief of Staff would hire a backfill and take another role inside or outside the company – most likely in a leadership capacity.

**Outcomes from the Chief of Staff to the CEO **

Coordination of processes and projects that involve multiple departmental functions

  • 30 Days: Consolidating existing company and department OKRs
  • 90 Days: Organizing an all-staff offsite; coordinating new OKRs; standardizing ways to ensure departments move institutional knowledge into the wiki
  • 365 Days: Re-designing product-sales interface/KPIs for next level of scale

**Execution of broad, strategic projects riddled with ambiguity **

  • 30 Days: Identifying an industry leaders to add to our advisory board
  • 90 Days: Updating company values; proposing headcount allocations
  • 365 Days: Helping evaluate, coordinate, and close M&A opportunities


Detail-oriented – This person will work with a lot of numbers and details of critical importance. Inaccuracies could cost the business millions.

Independent and self-managing – Learns and adapts without direct guidance. Independently identifies and self-directs to highest priorities among many. Accurately predicts required effort, time, and expense, especially for own projects. Ultimately delivers accurate timelines by reconciling with own capacity.

High-throughput, fast-paced context switcher – This person will have a lot to do. All at once.

Self-motivated – This job will be exceptionally challenging, busy, and often short-term unrewarding. We need someone who brings 110% no matter what, and who is eager to learn and to build the experience and exposure that this position enjoys.

Personable – This person will work with a lot of different personalities and will need to be liked in order to establish alignment among them.

Perks + Benefits

We believe that work should be meaningful and that employees should feel supported in valued which is why we prioritize investing in our employees These are a couple of ways in which we take care of our team:

  • Unlimited PTO + Paid holidays
  • Competitive Salary
  • Health Care, Vision and Dental (Available after 60 days)
  • Fully Stocked Kitchen with snacks (if in office)
  • The ability to work remote full time or come into an awesome office in the heart of Beverly Hills, CA
  • 401K
Apply HereContact Recruiter

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