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Head of Insurance

Job Posted
March 31, 2022

About GigEasy

The "gig economy" is rapidly becoming simply "the economy". Today, 1 in 3 Americans now works in the gig economy. Unfortunately, Gig workers cannot get much-needed benefits that are often offered to W-2 workers.

GigEasy is building a benefits company from the ground up for the gig economy.

Our first product is RentProtect by GigEasy, which covers your rent for up to six months in the event of sickness or injury.

GigEasy is a Platform Venture Studio company.

Platform was founded by 10x serial entrepreneur, Jeremy Burton (Wonolo, Fundly, Symbian) and seasoned venture investor, Tim Connors (founder/partner of PivotNorth, and former partner at Sequoia and USVP).

The Role

The Head of Insurance will work cross-functionally with product, engineering, and marketing teams to support the design, development, management, and end-to-end operations of innovative insurance products catered to the needs of the gig economy worker. The ideal candidate is entrepreneurial and collaborative with a sharp analytical mindset and superior communication skills.


  • Own overall strategy and build-out of consumer insurance products suited to meet the needs of the gig economy workforce
  • Recruit and build out our underwriting team.
  • Become the go-to expert for our insurance products, overseeing the coverage, pricing, underwriting, administration and compliance
  • Establish and maintain strong working relationships with insurance and product providers and strategic partners involved in the origination, underwriting, insuring, and servicing of the portfolio. This includes assessment and selection of Origination Partners, Third Party, and API requirements for the fulfillment of applications, decisioning, collateralization, funding onboarding, and servicing
  • Manage and grow relationships with product providers from discovery through implementation and ongoing reporting and evaluation
  • Be responsible for the growth and profitability of our Insurance product line through price optimization, determining insurance offering, filing, and rolling out to new geographies and customer segments.
  • Responsible for regulatory and compliance requirements of existing and new products including appointments and licensing requirements as well as monitoring of pending regulatory changes.


  • 15+ years of experience in the Insurance Industry, preferably in Innovation or Strategy
  • Possess a current Property & Casualty, Life and/or Health Insurance Producer License
  • Strong insurance technical skillsStrong analytical, quantitative, and problem-solving skills
  • Performance-driven, entrepreneurial, and self-motivatedAbility to work in a fast paced environment.

Preferred Experience

  • Wholesale Broker, Reciprocal or MGA experience
  • Insurtech Experience
  • TPA Licence


  • The ability to work from anywhere
  • Competitive compensation packages
  • Equity - we all own a part of the business
  • Unlimited Vacation
  • Health and wellness plans to meet the needs of you and your family including medical, dental, and visionSmart.
  • Supportive colleagues with diverse backgrounds and experiences
  • Plenty of GigEasy swag

GigEasy is an equal opportunity employer. We celebrate diversity and are committed to creating an inclusive environment for all employees.

How to Apply

Does this position sound like a good fit? Email us at

  • Include this role's title in your subject line (it'll help us to sort through the emails).
  • Send along links that best showcase the relevant things you've built and done.

Feel free to give us a call at 1-844-245-0518