Courageous Sailing Employment Application

We are glad you are interested in working at Courageous! Please complete this application to be considered for an available position. You will need to provide some basic personal information, answer some questions and upload a resume and cover letter.

Basic Information

Please complete with your permanent address.

Secondary Contact Information

Emergency Contacts

Emergency Contact #1
For Minors under age 18: This should be your parent or legal guardian.

Emergency Contact #2

How did you hear about Courageous?

Employment Opportunities

Youth Program Employment Opportunities

Select your preferred employment site, position and program. You may specify up to 3 position preferences.

Please note that some positions are only available at certain locations.

Adult Program Employment Opportunities


Cover Letter

Please write a brief (~300 word) narrative of your sailing experience and/or teaching experience. Explain why you would like to work at Courageous, why you're interested in your preferred positions, and how you will contribute to our team.

Accepted file types: .doc, .docx, .rtf, or .pdf


Submit your current resume with relevant education, sailing and/or teaching experience (if applicable) and at least 5 years of past employment experience, if applicable.

Accepted file types: .doc, .docx, .rtf, or .pdf

Returning Staff Application

We're thrilled that you're interested in returning to work at Courageous Sailing this summer! Applicants who worked at Courageous Sailing should complete this page in lieu of submitting a resume and cover letter. If you worked at Courageous Sailing in the past but not last year, you will need to submit a cover letter and resume.

Please include the name of the institution, degree attained, and dates of attendance.

Include 5 years of employment history, including name of business, job title, dates of employment, and job responsibility.

Instructor-in-Training (IIT) Essay **For new IIT applicants only. Returning IITs, please skip this page.**

Courageous Sailing’s mission statement is “Transforming lives through sailing programs that inspire learning, personal growth and leadership.” 

Please respond to one of the following (in 750 - 1250 words, or 1 - 2 typed pages in  single-spaced, 12 point, Times New Roman Font):

(1) Describe a situation in which you had to be a leader.

(2) Describe another individual whose leadership skills you admire.


All new applicants: Please provide contact information below of three references.

First time Youth Program applicants are responsible for sending this reference form to three references (not relatives). Three references must be received before Courageous can review your application for employment. 
Reference #1

Reference #2

Reference #3

Interest & Availability

Please note that all Youth Program staff are required to undergo a criminal background check.

Please note that not being available for the entirety of the program is not an automatic bar to employment.

This is purely for informational purposes and does not impact one's application eligibility or status for a position with the Summer Youth Program.

Additional Youth Program Work Opportunities

These are opportunities to work beyond the scope of the core Summer Youth Program. Availability and/or interest in these extra opportunities do not impact one's application status for the Summer Youth Program. This is purely for planning purposes.

To submit your employment application to Courageous Sailing please click submit below.