At SimplyInsured we are on a mission to eliminate fear in health insurance.

Health insurance is complicated, expensive, and really important - so it tends to create fear for most people; our goal is to reduce that fear as much as possible.

We specifically work with small business owners who have the enormous task of purchasing the right type of insurance for their employees and their families. With more than 20,000 customers and several major partnerships including Intuit and Square, we're growing quickly and disrupting this convoluted and confusing industry by making it more transparent and fully accessible to everyone. We got our start in the Y-Combinator incubator, and have been funded by top-tier investors at Polaris Partners, Bessemer Venture Partners, New York Life Ventures and AltaIR Capital.

Job Summary:

We are hiring our first Chief of Staff to work hand in hand with the CEO and our leadership team.

What you’ll do:

Communicate variances, identify associated risks and opportunities for optimization to facilitate decision-making
Communicate and be able to tell effective stories with data
Root cause analysis, project management
Ability to work with the CEO and be an extension to leadership
Lead strategic Board discussions and decisions (fundraising, budget planning etc.)

What you’ll bring:

Entrepreneurial-minded, taking action and solving problems proactively
Highly analytical & strategic, able to look at data and find the story
Ability to define & communicate company wide strategy
Strong interpersonal skills, ability to communicate and manage effectively at all levels of the organization
Promoter of a Data-Driven Company
Experience in a regulated industry (e.g. finance, insurance, real estate) is a plus

What we offer:

Generous stock option packages
Competitive compensation
Remote work environment
“Take what you need” time off plan
100% Medical, Dental, and Vision Insurance coverage
FSA plan
401k
A values-based culture that invests in employee success

Compensation:
The base salary range for this position is $160,000 to $190,000.

We have a market-based compensation structure. The salary for this position may vary based on a candidate's experience, industry expertise, technical skills, and location. The range provided is just one component of total compensation including, but not limited to bonus eligibility based upon the achievement of performance objectives and company stock options.

Our Culture:

We value radical transparency, feedback, bias to action, growth, and an obligation to dissent. Every opinion is respected, we hold each other to extremely high standards, we're driven by the diversity in our backgrounds, and unified by 100% alignment on our mission.

Research shows that candidates from underrepresented backgrounds often don't apply for roles if they don't meet all the criteria. We strongly encourage you to apply if you're interested; we'd love to learn how you can amplify our team with your unique experience!

We are an equal opportunity employer and value diversity at our company. We do not discriminate on the basis of race, religion, color, national origin, gender, sexual orientation, age, marital status, veteran status, or disability status.

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