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Join the SimplyInsured Team



SimplyInsured is “Kayak for Health Insurance” - we are a 100% online platform to buy small business health insurance. We are revolutionizing the $17B health insurance brokerage market. We have hundreds of delighted customers, are generating revenue, and are backed by YCombinator and some of silicon valley’s top entrepreneurs and investors.


Open Positions:


What we look for:

  • Strong desire to build, to sell, and to win
  • Great people who want to fundamentally transform the insurance industry
  • Self starters with a history of building (and breaking) things
  • Ability to work quickly in a small team environment

What we offer:

  • Generous stock option packages
  • Lunch and Dinner every day (along with healthy snacks)
  • Team-building activities like wine tastings and free (as in beer) beer
  • Health, Vision, Dental Insurance (duh!)

Email us your resume at jobs@simplyinsured.com .


Full Stack Hacker

Like breaking the rules and hacking software systems? We are looking for hackers and generalists that like using software to win. Don’t hesitate to get in touch - we are built on Ruby on Rails, but we just want you to be smart and get stuff done.

What we look for:

  • Demonstrated experience hacking elsewhere - code samples are best (share your github, personal website, previous projects, etc.)
  • Will do everything from tweaking nginx on our servers, to building analytics and marketing solutions, to designing entirely new insurance services
  • Work hard - play hard, strong desire to build product and win
  • Technical background: a degree in CS, EE, math, physics, molecular gastronomy, etc.
  • Bonus points if you have worked at a startup

Office Manager/Executive Assistant

Like keeping the trains running on time for a fast growing office? Do you like growing sales as fast as humanly possible? Enjoy the challenge of managing people, vendors, an office, and an executive's schedule? You will be the face of the office - everyone and everything that comes into the office will be your responsibilty - coordinating recruiting, managing lunch/dinner and deliveries, and helping manage the CEO's calendar.

What we look for:

  • Love to organize, coordinate, and keep the trains running on time
  • Strong communication, organization, and management skills
  • Flexibilty to wearing many hats and excelling at new challenges
  • Work hard - play hard, strong desire to keep the office running smoothly

Business Development/Revenue Growth

Do you like growing sales as fast as humanly possible? Then this role is for you. As a business generalist - you'll be working on sales, marketing, partnerships, underwriting, state expansion, support - if it requires facing the customer and growing our sales - you will be owning it.

What we look for:

  • Passion for sales and revenue growth
  • Strong communication, organization, and sales skills
  • Flexibilty to wearing many hats and excelling at new challenges
  • Work hard - play hard, strong desire to help businesses get SimplyInsured

Operations Manager

Our operations are complex - your job is to make them simple. We are hiring an experienced operations generalist. You will be responsible for the flawless and speedy execution of insurance processes. This includes optimizing billing and payments, speeding up data retrieval from customers, and working with customer processes to help get insurance faster.

What we look for:

  • Passion for making onerous processes simple and quick
  • Highly detailed and process oriented thinking
  • Problem solving skills to navigate complicated issues
  • Work hard - play hard, a strong desire to simplify operations to grow the company

Client Success Manager

Happy and healthy clients are your bread and butter. We are hiring an exceptional customer service represenative. Your job will be to fight on behalf of our clients, their employees, and their families - against insurance companies, doctors, and billing departments. On the phone, email, or in person, we win when our clients are happy with their insurance.

What we look for:

  • Positive and optimistic personality - no client problem is too big
  • Passion for making people happy - especially when it comes to their health
  • Problem solving skills to navigate complicated issues
  • Work hard - play hard, a strong desire to simplify operations to grow the company

Email us your resume at jobs@simplyinsured.com .