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Claims Supervisor

Squaremouth is looking for a Claims Supervisor for our travel insurance brand Tin Leg. The ideal candidate will be sociable, passionate about their work, laid-back and fun. They must have at least 5 years of claim leadership experience. A current Florida adjuster license in good standing is required. Multiple state adjuster licenses are preferred.

The successful candidate will be responsible for adjusting travel insurance claims and managing a small team of adjusters. They should possess a superior knowledge of insurance contracts and claim adjusting principles. They need to be able to set, communicate and monitor the performance of team members.

We are seeking a self-motivated individual who has an intrinsic desire for personal growth and professional success, and who strives to be an expert in our industry. They will teach themselves, learn from others, and take ownership of their successes and challenges. This person must be a team player as Squaremouth is a highly collaborative environment.

Responsibilities and Requirements

  • Supervises all activities of the claim department
  • Handles claims
  • Ensures adequate staffing
  • Monitors workload and reviews claims
  • Establishes and implements policies and procedures
  • Educates and develops claims staff
  • Ensures claim handling adheres to the requirements of the underwriter and in accordance with state regulations
  • Assists in developing internal claim handling system


  • Bachelor's degree
  • 5 or more years of adjusting experience
  • At least 3 years of leadership experience
  • Florida adjuster license required
  • Insurance designations preferred

What we offer

Competitive salary based on experience
Revenue share
Unlimited paid vacation (minimum 10 days off required)
Paid medical
401k match
Mandatory birthday off with $200 beer bonus
Access to the Squaremouth company boat
Automatic CPI increase every January
Rapid promotion
Free parking
Involvement in major Squaremouth decisions and future direction, including pay raises and new hires

Who we are

Squaremouth is America’s fastest growing travel insurance comparison site. The company has received national recognition for its unique workplace culture and business growth. Recent accolades include INC Magazine’s 2017 Best Workplaces in America, Fortune’s #2 Workplace for Women in America, and one of Inc.’s Fastest Growing Companies.

Squaremouth founded Tin Leg travel insurance in 2014. Tin Leg's products are designed to provide travelers with comprehensive coverage, including in-demand Trip Cancellation benefits and high Primary Emergency Medical coverage.

Tin Leg’s award-winning customer service department, dedicated 24 hour emergency support, and revolutionary claims process, have established the company as a trusted leader in the travel insurance industry.

The Squaremouth offices located in St. Petersburg provide a unique environment with free beer on tap, no assigned desks, wide open work spaces, a nap area, and pool tables.

Squaremouth’s organizational structure is relatively flat, promoting transparency, open communication, and group decisions. Everyone knows how much everyone makes, and the company’s unique raise policy was recently featured in the Business Observer. At any time, employees can request a pay raise, which is determined by a majority vote from their co-workers.

Local candidates only.

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