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Clover Health — Unlimited PTO Jobs

Technology-driven Medicare Advantage insurer using the Clover Assistant platform to support primary-care physicians treating seniors. Verifies "No Meeting Fridays" on its public careers page under Mental Well-Being.

5 day weekUnlimited PTONashville, United StatesMedium (51-200)Fully Remote

About Clover Health

What is Clover Health?

Clover Health (Nasdaq: CLOV) describes itself as "a physician enablement technology company committed to bringing access to great healthcare to everyone on Medicare." In practice it runs Medicare Advantage health plans — "Preferred Provider Organization ("PPO") and Health Maintenance Organization ("HMO") Medicare Advantage ("MA") plans for Medicare-eligible individuals" — and builds the software its doctors use.

That software is the core of the business. "Our proprietary software platform, Clover Assistant (licensed externally as Counterpart Assistant), helps us execute this strategy by enabling physicians to detect, identify, and manage chronic diseases earlier than they otherwise could. This technology is a cloud-based software platform that provides physicians with access to data-driven and personalized insights for the patients they treat." In 2024 Clover launched Counterpart Health, "a new Software-as-a-Service ("SaaS") and Tech Enabled Services Solution to bring the power of Clover Assistant technology to external payors and providers."

Clover Health was incorporated in July 2014 and co-founded by Vivek Garipalli, now Executive Chairperson, who was CEO until December 2022. Andrew Toy is the current CEO. As of 1 January 2026 the company "operated our MA plans in five states and 203 counties" — Georgia, New Jersey, Pennsylvania, South Carolina and Texas — serving over 150,000 Medicare Advantage members, and it reported its first quarter of positive GAAP net income in Q1 2026.

Where will I work?

Almost certainly from home. "Clover Health is a remote-first company. Accordingly, we do not maintain a corporate headquarters," and its annual report lists "Item 2. Properties. Not applicable." The careers page adds: "The majority of our roles are 100% remote and we offer a home office reimbursement for full time employees."

The company frames this as deliberate: "We operate a distributed team model from the Board of Directors on down within our organization, and we believe that our distributed approach to teams allows us to attract the best talent for each and every role, without geographic constraints." Teams are "based in the United States, Hong Kong, Canada, New Zealand and beyond," including a Hong Kong office opened in 2018. Note that field and clinical roles are tied to Clover's plan states.

What is the Clover team like?

Clover reported 724 employees at 31 December 2025, roughly 93% in the US and 6% in Hong Kong. Hiring spans engineering, data science, product, clinical, plan operations and field roles, and job ads are posted for both Clover Health and its Counterpart Health subsidiary.

Work-Life Balance

Clover is a full-time-week employer — it publishes no four-day week or reduced-hours policy — but it protects time deliberately in three ways.

First, "No Meeting Fridays": a company-wide meeting-free day. This is a working day with the calendar cleared, not a day off. Second, at least one paid company-wide holiday every month, which is what produces the "monthly three-day weekends" Clover advertises, plus a paid year-end "Week of Rest". Third, a flexible time off policy for salaried staff — though note that field and clinical roles instead "accrue up to 18 days of vacation per year" alongside 10 federal holidays, 4 additional paid holidays and a floating holiday.

Perks and Benefits

  • "No Meeting Fridays" — a company-wide meeting-free working day
  • At least one paid company-wide holiday per month, plus a paid year-end "Week of Rest"
  • Flexible time off for salaried roles; up to 18 accrued vacation days for field and clinical roles
  • Remote-first — the majority of roles are 100% remote, with no corporate headquarters
  • Comprehensive medical, dental, vision and telehealth for employees and their families
  • Mental health resources
  • Paid parental leave for all new parents
  • 401(k) with company match and an Employee Stock Purchase Plan at a discount
  • Performance-based bonus programme and regular compensation reviews
  • Home office setup reimbursement plus a monthly cell phone and internet stipend
  • Learning programmes, mentorship and professional development funding

Open Positions

42 jobs