Sidecar Health application questions — all 34, word for word

Sidecar Health hires through Greenhouse. Beyond name, email and CV, its application form asks 34 questions, 27 of them required. 4 of them are required, fixed-choice questions about your eligibility to work. A cover letter is optional.

14 roles were open when this was last checked, mostly in engineering and support. The questions below are the form's own wording, not a paraphrase.

What Sidecar Health has open

These are the roles the form was read from, as Sidecar Health titles them, in Remote:

31 of the questions below are ones at most two of the 212 employers measured ask (median: 13), the least standard being “Do you have 3+ years of experience in appeals and grievances, claims adjudication, utilization review, or a related health insurance operations role?”.

The eligibility questions

These are required, and answered from a fixed list rather than in your own words: work authorisation, visa sponsorship or security clearance. Employers often use questions like these to filter applications automatically, but Greenhouse's public data does not say whether Sidecar Health does — so treat them as the answers most likely to matter, not as a verdict. Answer them honestly either way.

QuestionAnswers accepted
Are you authorized to work in the United States? required, fixed choice Yes, No
Do you now or will you in the future require sponsorship or employment authorization to work in the US? required, fixed choice Yes, No
Are you authorized to work in the United States without current or future visa sponsorship? required, fixed choice Yes, No
Will you now or in the future require visa immigration sponsorship to work in the United States? required, fixed choice Yes, No

Every question on the form

QuestionTypeRequired
Are you authorized to work in the United States?
Yes, No
select Yes
Do you now or will you in the future require sponsorship or employment authorization to work in the US?
Yes, No
select Yes
Are you authorized to work in the United States without current or future visa sponsorship?
Yes, No
select Yes
Will you now or in the future require visa immigration sponsorship to work in the United States?
Yes, No
select Yes
First Name text Yes
Last Name text Yes
Email text Yes
Phone text Yes
Resume/CV file Yes
Cover Letter file No
LinkedIn Profile text No
Please briefly share your experience in health insurance or employee benefits. textarea Yes
Do you currently reside in the Dallas/Fort Worth, TX area?
Yes, No
select Yes
Do you have a Texas State Health and Life insurance license?
Yes, No
select Yes
Are you willing to travel up to 40%?
Yes, No
select Yes
Do you have a Bachelor's degree?
Yes, No
select Yes
If someone referred you from Sidecar Health, please list their name. text No
What are salary expectations? text No
Do you live in the greater Columbus, OH area?
Yes, No
select Yes
When are you available to join a new position? text No
Do you have reliable transportation and comfortable with 30% travel?
Yes, No
select Yes
What are your compensation expectations? text Yes
After reading this job description - why do you think you'd be a good fit for this position? textarea Yes
If you were referred, which Sidecar Health employee referred you? text No
Website text No
Do you live in California?
Yes, No
select Yes
Preferred First Name text No
Are you currently located in California and able to work from either the Los Angeles or San Francisco area?
Yes, No
select Yes
What city and state do you currently live in? text Yes
Do you have AI experience?
Yes, No
select Yes
Do you have a bachelor's degree or higher?
Yes, No
select Yes
Do you have 3+ years of experience in appeals and grievances, claims adjudication, utilization review, or a related health insurance operations role?
Yes, No
select Yes
Do you have working knowledge of health insurance regulatory requirements for appeals and grievances (e.g., state DOI requirements, ERISA, ACA)?
Yes, No
select Yes
What is your salary expectation? text No
Do you currently reside in Florida, Georgia, North Carolina, Ohio, Texas or Utah?
Yes, No
select Yes
Do you reside in Colorado, Florida, Georgia, Minnesota, North Carolina, Ohio, Texas or Utah?
Yes, No
select Yes
Have you owned the end-to-end design and delivery of a training program in a contact center or customer service environment?
Yes, No
select Yes
Please briefly describe your experience designing and delivering training programs and the environment you did it in. textarea No
Were you referred to this role by someone at Sidecar Health?
Yes, No
select Yes
Do you live in Georgia?
Yes, No
select Yes
Do you have reliable transportation and are you willing to drive up to several hours across Georgia to service members?
Yes, No
select Yes
Do you have healthcare or insurance experience? If so, how many years? text Yes

What it's really asking about

Grouped by what each question is for, so you can prepare the answers that repeat across employers.

TopicQuestions
Remote or on-site 7
Other 6
Years of experience 4
Education 3
Salary expectations 3
Visa sponsorship 3
How you heard of them 2
Role-specific screening 2
Cover letter 1
Relocation 1
Start date 1
Work authorisation 1

What other employers ask

The same question rarely comes out the same way twice. These employers' forms are measured the same way, from their own job boards:

Samsara · Scopely · Shopmy · Signifyd · Singlestore · Smartsheet

Before you apply

Have the answers to the required questions ready before you open the form — Sidecar Health's asks for 27 of them, and Greenhouse does not save a partial application by default. Settle the eligibility questions first — they are the ones with no room to elaborate, so knowing your answer before you start tells you whether the rest of the form is worth your time.

Data gathered from Greenhouse's public job board API on 2026-08-22. How this data is collected · All companies · Something wrong? Tell us and we'll fix it within 24 hours.

Source: https://boards.greenhouse.io/sidecarhealth