Employment Opportunities

Thanks for your interest in Kollegewidgwok Sailing Education Association (KSEA). Our instructional and leadership positions are now open for summer 2025 and we are looking for fun, qualified candidates. Please view below for information about our opportunities and send us an email at kseaprogramdirector@gmail.com if you have any questions

Perspective teenage volunteers, please fill out the 2025 KSEA Volunteer Form.


instructors and leadership for summer 2025.

Application deadline: Friday, January 3, 2025 @ 11:59pm. If interested after this deadline, please submit your application for us to keep on file.

Welcome to the application process for the summer of 2025.  As part of the application process our program director would like to have you share your strengths, challenges and aspirations for yourself and the people you plan to lead in the KSEA program.

All positions run Mon-Fri from June 16 - August 22, 2025. We know that school schedules vary and can discuss accommodations that you might need related to schedules.

Below are the current roles at KSEA. Please read through each job description before you answer the application questions. 

  • Head Instructor

  • 420/Bull’s Eye Fleet Captain

  • Optimist/Pram/Rowing Fleet Captain

  • C420 Race Team Coach

  • Optimist Race Team Coach

  • Instructor

  • Junior Instructor

  • Volunteer 

The questions following will allow the KSEA hiring team to learn about your aspirations for the program and for yourself at KSEA. Please reach out to Jenny Cahalan at kseaprogramdirector@gmail.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 2025 summer.

  2. What makes you a good fit for each of these positions? Think personality traits, leadership skills, sailing/racing/coaching skills, relevant non-sailing skills… 

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

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

  6. How have you grown over the past year (you can break it up into how you grew in summer 2024 and how you might have grown so far in the offseason? 

  7. What is one sailing or boating skill you excel at? What is one that you are looking to practice and gain more knowledge/experience? 

  8. What is a special interest you might want to commit to for Summer 2025? This could be something that's not necessarily in anybody’s job description, but something KSEA would benefit from. Examples (of which you’re welcome to use and elaborate on) include girls and women in sailing, learning and implementing proper boat tuning, fiberglass work, hype person for potlucks/movie nights, friday snackday, Pirate Day chairperson, etc. 

  9. What does accountability mean to you? 

Once you have completed the applications questions, please send them in a simple email to kseaprogramdirector@gmail.com. This will serve as your complete application.

Perspective teenage volunteers, please fill out the 2025 KSEA Volunteer Form.

  • 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 and the leader among all sailing and rowing instructors. The head instructor will report to the program director and work closely with the KSEA Board, parent volunteer coordinators, and all instructors throughout the summer.

    The Head Instructor should fulfill the requirements and uphold the duties and responsibilities of an Instructor. In addition, responsibilities include:

    • Leading by example in 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 launching and hauling of sailing equipment at the beginning and end of the season; working with the fleet captains to track sailboat and rowboat maintenance 

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

    • Upholding program safety policies and high staff expectations

    • Providing sailing instructors and coaches with support and regular feedback

    • With the program director, club 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 & junior instructors, supporting other team members both on & off the water

  • As members of the KSEA leadership team, the two Fleet Captains will oversee all aspects of maintaining and managing the KSEA fleets.  They will be the team “experts” on the fleet and 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.

    The Opti, Pram, and Rowing Fleet Captain should fulfill the requirements and uphold the duties and responsibilities of an Instructor. In addition, 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 staff’s inquiries regarding class placement

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

    • Communicating with instructors and coaches to keep an informal repair log

    • Making repairs to equipment where possible, and delegating/communicating issues that can’t be immediately fixed to the program director. 

    • 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

    • Check in daily with junior instructors leading Rowing classes to help manage curriculum, kid behavior, and ensure safety and learning. 

  • As members of the KSEA leadership team, the two Fleet Captains will oversee all aspects of maintaining and managing the KSEA fleets.  They will be the team “experts” on the fleet and 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.

    The 420/Bull’s Eye Fleet Captain should fulfill the requirements and uphold the duties and responsibilities of an Instructor. 

    In addition, 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 & junior instructors in teaching those classes

    • Responding to staff’s inquiries regarding class placement

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

    • Communicating with instructors and coaches to keep an informal repair log

    • Making repairs to equipment where possible, and delegating/communicating issues that can’t be immediately fixed to the program director

    • 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 & junior instructors, supporting other team members both on & off the water

  • The 420 Race Team Coach will work with the fleet captains and the head instructor to manage the 420 race team. A volunteer race team coordinator (likely a race team parent or KSEA Board member) will work to support the race team coaches as well.  

    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.

    The 420 Race Team Coach should fulfill the requirements and uphold the duties and responsibilities of an Instructor. In addition, 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

    • Hold a pre-season informational meeting for parents and sailors

    • Planning and executing daily lesson plans to refine sailors’ knowledge of boat handling, boat speed, tactics & strategy, emphasizing the racing rules of sailing and sportsmanship

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

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

    • Deciding race team pairs and regatta rosters, and communicating pairing information to the program director, parents, and sailors

    • Providing on-the-water coaching at regattas

    • Providing weekly goals and feedback to sailors

    • Assessing readiness for sailors to move up to race team and communicating that readiness to sailor, parents, and instructor team 

    • Partnering with local programs for team racing practice

    • Providing the program director, head instructor & fleet captains with timely information about calendar events, including notices of race, registration information, trailer loading day, travel day, and regatta day schedules, etc.

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

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

  • The Opti Race Team Coach will work with the fleet captains and the head instructor to manage the Opti race team. A volunteer race team coordinator (likely a race team parent or KSEA Board member) will work to support the race team coaches as well.  

    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.

    The Opti Race Team Coach should fulfill the requirements and uphold the duties and responsibilities of an Instructor. In addition, 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

    • Holding a pre-season informational meeting for parents and sailors

    • Planning and executing daily lesson plans to refine sailors’ knowledge of boat handling, boat speed, tactics & strategy, emphasizing the racing rules of sailing and sportsmanship

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

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

    • Deciding regatta rosters, and communicating pairing information to program director, parents, and sailors

    • Providing on-the-water coaching at regattas

    • Providing weekly goals and feedback to sailors

    • Assessing readiness for sailors to move up to race team or onward to 420 race team, and communicating that readiness to sailor, parents, and instructor team

    • Partnering with local programs for team racing practice

    • Providing the program director, head instructor & fleet captains with timely information about calendar events, including notice of races, registration information, trailer loading day, travel day, and regatta day schedules, etc.

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

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

  • 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. You must be 18 years old and hold a US Sailing Level 1 Small Boat Instructor Certification.

    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:

    • Working during set up and clean up weeks to prepare campus for the season and pack equipment away at the end of the season

    • 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 junior instructors, including chalk talks, on-the-water instruction, coach boat handling and mark setting

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

    • Playing an active role in potlucks and movie nights, helping to set up and clean up, generally being helpful to parent volunteers, and mingling with sailors and their families

  • You must be 16 years old to be a junior instructor.

    Over the course of the summer, Junior Instructors will be exposed to a variety of classes across the different fleets, including rowing and be asked to learn, build and practice skills to set themselves up for future success as an instructor. 

    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. Please reach out to Jenny at kseaprogramdirector@gmail.com if you’d like to discuss an exception to this eight week long half-day commitment. 

    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 & junior instructors, supporting other team members both on & off the water

    • Leading rowing classes on daily adventures under supervision of nearby instructors. 

    Before the first day of work, Junior Instructors will be expected to know the following information and skills:

    • Tie a bowline

    • Tie a square knot 

    • Tie a cleat hitch

    • Coil a line

    • Rig an Opti sail 

    • Rig a 420 with proper halyard tensions 

    • Rig a Bullseye 

    • Sail a Bullseye with minimal assistance

    • Know the simple basics of driving a powerboat 

      • Wear a kill cord

      • How the throttle works–forward, neutral, and reverse

      • Importance of keeping lines, especially bowline, tidy and secured 

  • We will continue our tradition of welcoming early teen volunteers to assist our instructional staff. Interest forms submitted by April 1st will be prioritized. Please fill out the 2025 KSEA Volunteer Form here. Please email kseaprogramdirector@gmail.com with any questions.