Chief of Staff

Fairsquaremedicare

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New York Until 8/22/2026 H-1B sponsor history First posted March 21, 2025 Last posted March 21, 2025
Job description

Fair Square is profitable and expanding across two business lines: vertical SaaS and DtC health insurance.

You will work daily with the CEO on product operations, cultivating relationships that will lead to multi-million dollar deals, and developing novel, creative and envelope pushing customer acquisition strategies.

You must be a high-energy go-getter. Must have rizz. Must be able to build systems. Must be able to write. Must be an original thinker. Must be quantitative. Must be able to point to past wins. Past successful and entrepreneurial or college/amateur/pro athletic experience are a plus.

If interested, email: dan at fairsquaremedicare.com. Subject line: Chief of Staff.

About this role

Summary

Work with CEO on operations and develop customer acquisition strategies.

Job title

Chief of Staff

Experience level

5+ years

Industry

health insurance

Location requirements

Located in New York, remote work not allowed

Salary

Not specified

Visa sponsorship

H-1B sponsor history

Management role

Yes

Skills & keywords

Required skills

build systemswritingoriginal thinkingquantitative analysispast wins

Preferred skills

entrepreneurial experiencepro athletic experience

Specializations

product operationscustomer acquisitionrelationship buildingquantitativeentrepreneurial
Locations

Structured locations inferred from the posting.

New York, NY, USA

On-site City