KSEA is Hiring Sailing Instructors and Coaches!

Job Posted 11/28/2023
Kollegewidgewok Sailing Education Association
KSEA 44 KYC Lane
Blue Hill, ME 04614
United States
Summer Only
Summer Only
Experience Required
Housing Provided
Job Start Date
Job End Date
Application Closing Date
Job Description


KSEA Staff Application

Welcome to the application process for the summer of 2024. As part of the application process the hiring committee would like to have you share your strengths, challenges and aspirations for yourself and the people you plan to lead in the KSEA program. We started this process last year and it was very helpful for getting to know our applicants and your thoughts about the program. If you had a position last year, please know that this is an opportunity to express what you have learned and how to bring that into the coming year, and to indicate interest in the same or a different position. We at the KSEA Board envision an environment of support for growth of our participants and instructors, in both skills on the water and in leadership. We look forward to your answers to the questions. Please read on for a brief description of the KSEA structure and positions available for the 2024 summer.

Your application, including the answers to the questions at the bottom are due January 3rd. You may email your responses to the questions to kseasail@gmail.com.

KSEA Positions for Summer 2024

All positions run Mon-Fri from June 17 - August 23, 2023

(We know that school schedules vary. We can discuss any accommodations that you might need related to schedules.)

See detailed job descriptions below. Please indicate in which position(s) you are interested. If you have an interest in Race Team please let us know (even if you are not applying to be a coach.)

Leadership Team –The following three positions will serve as the leadership team at KSEA. The fleet captains will work closely with the head instructor to address challenges as a team and work in a seamless way to support the KSEA mission.

  • Head Instructor

  • Opti/Rowing Fleet Captain

  • 420/Bullseye Fleet Captain

Race Coaches –The race coaches will work with their fleet captains and the Head Instructor to manage the race teams. A volunteer race team coordinator (likely a race team parent or KSEA Board member) will work to support the race team coaches as well.

  • Opti race coach

  • 420 race coach

Full-Time Instructors– The full-time Sailing Instructor positions are ideal for instructors open to teaching a variety of different classes. These positions are important to allow for a flexible program. They also allow instructors to develop leadership skills while experiencing many aspects of the KSEA program. To be a full-time Instructor, you have had experience as a JI and are ready for the responsibility of being a full-time instructor. You must also be 18 years old and have your US Sailing Level 1 Certification.

Junior Instructors-This position is for novice instructors, learning methods and best practices for teaching sailing. You will work closely with more experienced instructors and coaches, assisting with both on & off the water instruction. Over the course of the summer, you will be exposed to a variety of classes across the different fleets, including rowing. You must be 16 years old to be a junior instructor.

KSEA Job Descriptions

Head Sailing Instructor

The Head Sailing Instructor is responsible for the safe, smooth, and organized daily operation of the KSEA sailing program, including all on-the-water activities and special events. The Head Instructor is the face and spokesperson of the program, the most senior full-time employee and the leader among all sailing and rowing instructors. The Head Instructor will report to the club’s manager and work closely with the KSEA Board, parent volunteer coordinators, and all instructors throughout the summer.

Responsibilities include:

  • Leading by example, setting a high bar for staff reliability, safety, and consistency

  • Working closely with the fleet captains & race coaches to develop class curricula and daily lesson plans

  • Ensuring grounds and equipment are prepped for classes each morning, and that all equipment and coach boats are stored properly at the end of each day

  • Supervising the hauling and launching of equipment at the beginning and end of the season; working with the fleet captains to track maintenance of 420, Opti, Rowing and Bullseye fleets

  • Acting as a primary point of contact for inquiries related to the KSEA program. Maintaining an open line of communication with fellow instructors, participating sailors and parents

  • Upholding program safety policies and high staff expectations

  • Providing sailing instructors and coaches with support and regular feedback

  • With the Club Manager, Program Manager & Fleet Captains, planning and executing annual special events like Pirate Day, potlucks and race teas.

  • Working as part of a cohesive team of KSEA instructors, coaches & JIs, supporting other team members both on & off the water

Fleet Captains

As members of the KSEA leadership team, the Fleet Captains will oversee all aspects of maintaining and managing the KSEA fleets. They will be the team “expert” on the fleet equipment, the course curriculum for their fleet and the sailors participating in those classes. They will also work closely with the race team coach to assess equipment for racing and travel to races.

Responsibilities include:

  • Reviewing the curriculum for each class in their fleet at the beginning of each season, making updates as needed

  • Overseeing daily lesson plans, supporting instructors & JIs in teaching those classes

  • Responding to inquiries re: class placement

  • Ensuring that the equipment is properly cared for, stored & maintained. This includes boats, trailers, waterfront racks & docks

  • Working closely with race coaches to manage sailboat and coachboat coverage, especially when race teams are traveling to regattas

  • Meeting regularly with the head instructor and race coaches to provide updates specific to their fleet

  • Working as part of a cohesive team of KSEA instructors, coaches & JIs, supporting other team members both on & off the water

Opti & 420 Race Coaches

The Race Coaches are responsible for the leadership & coaching of the Opti & 420 race teams. This will involve daily instruction as well as on-the-water coaching at local & travel regattas. The race teams are small but dedicated, and we expect the race coaches to foster a positive team environment where racers feel both challenged and supported by their teammates and coaches.

Responsibilities include:

  • Developing a summer-long racing syllabus.

  • Developing a summer-long regatta calendar to be distributed to race team families at the start of the summer.

  • Planning and executing daily lesson plans to refine sailors’ knowledge of boat handling, boat speed, tactics & strategy as well as racing rules

  • Working closely with the fleet captains on boat maintenance throughout the summer

  • Working with the race team parent coordinator to organize and supervise travel to and from local and regional regattas

  • Providing on-the-water coaching at regattas

  • Partnering with local programs for team racing practice

  • Providing the Club Manager, Head Instructor & Fleet Captains with timely information about calendar events, including NOR, registration information, etc.

  • Assisting with the hosting and running of regattas hosted by KSEA

  • Working as part of a cohesive team of KSEA instructors, coaches & JIs, supporting other team members both on & off the water

Full-Time Instructors

The Full-Time Instructors are responsible for leading daily lessons for Opti, 420 & Bullseye sailors, focusing on beginner to intermediate sailing instruction, water safety, boat handling & knot tying. The Instructors will maintain a safe environment for all sailors while providing a fun & exciting learning environment.

Responsibilities include:

  • Planning and executing daily lesson plans to refine sailors’ knowledge of rigging & derigging, boat handling, boat speed, basic seamanship and racing rules

  • Working closely with the fleet captains on implementing class curriculum and determining class placement for sailors

  • Creating learning opportunities for the JIs, including chalk talks, on-the-water instruction, coach boat handling and mark setting

  • Working as part of a cohesive team of KSEA instructors, coaches & JIs, supporting other team members both on & off the water

Junior Instructors

The JI position is ideal for aspiring instructors and coaches, beginning to develop their skills as a sailing instructor. This position is a support for the sailing education and the KSEA leadership at all levels. Working side-by-side with more experienced members of the team, you will learn methods of instruction, strategies for leading an engaging & informative class and best practices for maintaining a safe learning environment. In most cases, this is a half-day position.

Responsibilities include:

  • Assisting the senior members of the instructor team in leading their classes. This may include participating in chalk talks, setting marks, assisting sailors in rigging & derigging boats, setting tow lines, monitoring sailors on the water and generally helping out where needed.

  • Working as part of a cohesive team of KSEA instructors, coaches & JIs, supporting other team members both on & off the water


The questions following will allow the KSEA Board to learn about your aspirations for the program and for yourself at KSEA. Please reach out to River at manager@kycbluehill.com if you have questions during this process.

Please answer the following questions in an in-depth manner. You may need to read through them and think about them before addressing them fully. There is no prescribed word count per answer, as some of you have minimal experience and others, more to write about. This is your opportunity to engage with each topic. Please include the question with your answer.

  1. Please list all of the above positions of interest to you for the 2024 summer. For each position, list experience you believe qualifies you for the position.

  2. Please list all past instructor positions at KSEA, or at another sailing program, including volunteer positions. Can truly be a list.

  3. What positions do you aspire to, but may not be ready for at this time? This is your opportunity to express your own personal vision for your role at KSEA in the future so we can assess how best to support you in that growth.

  4. Please describe your experience and proficiency with sailing (KSEA and other), including regatta experience. May organize this section by boat type and years of sailing experience. Please differentiate race team, or regatta experience from cruising/pleasure sailing. Please share important accomplishments.

  5. What makes you an asset to KSEA’s sailing program?

  6. What are your personal areas for growth as an instructor and how can leaders support you in this growth?

  7. What does working at KSEA mean to you? If not previously a KSEA sailor or instructor, what does teaching in a sailing program, generally, mean to you?

  8. In your experience, what are three to five things that KSEA does well? If not previously a KSEA sailor or instructor, explain three to five things that a program you have been involved with has done well?

  9. In your experience, what are three to five things that KSEA can do to improve? If not previously a KSEA sailor or instructor, suggest three to five ways a program you have been involved with could improve.

  1. Phones are a constant in our lives, but not appropriate to use most of the time at work. The KSEA work environment requires attention to safety and learning, and in a setting where we are working around others, many types of boats and changing conditions. Phones are a barrier to our efficiency and effectiveness, but may be useful in some circumstances. What are some suggestions you have for how to manage phones in this work environment?

  1. KSEA has an hour at the end of the day after classes end that is often underutilized. Given your experience, how do you propose that we use that last hour of the day as a team?

  1. Race pairings can be a stressful and fraught process. What suggestions do you have for pairing up sailors for race teams, regattas and race days? *This question is for those who have experience on 420 race team as a sailor or instructor.

    13. Junior Instructors are an important part of our sailing instruction team. Do you have suggestions for the best way to structure this position to maximize learning for the JIs and benefit the Instructor staff? *This question is for those who have already worked at KSEA or a sailing program with similar roles.


Job Requirements
Multiple jobs. Please read listing for positions and instructions for applying. Sailing Experience needed. US Sailing Certification required for Instructors, Fleet Captains, Coaches and Head Instructor. Race Coaches will have some travel to regattas.
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