Apply to work at Lakeside Watersports this Summer!
Lakeside Watersports: Team Sessions!
A brief visual of what it’s like to be part of the Lakeside Watersports Team! We are not your average Summer Job.
Lakeside Watersports is an Equal Opportunity Employer
Fill out the application form below to be considered for open positions we are actively looking to fill for this summer season on Candlewood Lake.
Available Positions:
Boat Driver/Watersports Instructor
Deckhand/Spotter
Greeter / Receptionist
Connor’s assistant
About Lakeside Watersports:
Get ready for an exciting summer on Candlewood Lake! Lakeside Watersports is back for its 3rd season at Echo Bay Marina and is the leading watersports provider in Connecticut. We offer private, hour-long lessons in wakeboarding, waterskiing, wakesurfing, and tubing adventures.
Founded by a local Candlewood Lake enthusiast, our goal is to share the thrill of watersports with as many people as possible. We are proud of our growing customer base and the positive reputation we've established around the lake.
At Lakeside Watersports, we are dedicated to providing top-notch service and creating unforgettable experiences on the water. Apply today and join us a team of experts for a summer of fun on Candlewood Lake!
"Lakeside Watersports purpose is to give public access to Candlewood Lake for an affordable price to people who want to learn any type of watersports (Wakeboarding, waterskiing, wakesurfing)! We train our customers on watersports instruction, and safe boating!" - Connor Kostyra - Owner / Watersports Instructor
Why work for Lakeside Watersports?
In any of the positions here at Lakeside Watersports, there’re 3 reasons why you should work with us. Experience, Education, and mainly Lifestyle!
We change our staff a little every year because people move onto other jobs or we need a change of people. We’re a seasonal business that only operates for a portion of the year. Specifically, the summer time in Connecticut on Candlewood Lake.
The first reason to work for Lakeside Watersports is the experience. We are a unique company that is not normal in the sense of a “summer job”. We are actually extraordinarily above average, and you being part of our team is your first step in proving your value in the “job” world. Find us a better summer job than working for us, and we will invest in that business! Our job at Lakeside is to prepare you for the social interactions of talking with customers, and teaching people new skills they have never learned. These skills prepare you for the life of sales. When we say sales, we mean in selling yourself as a person, and your value. The connections you will make on these boats with our customers you will remember for life. Our customers are very high net-worth individuals, and you will be able to talk with them on a very casual low pressure level, when they are at their peak of fun with the family!
The second reason to work for Lakeside Watersports is the education. Let’s start off by declaring, if you’re good at watersports, you will be even better after a summer with us on our Wednesday Sessions. It’s our mission here to make sure you’re knowledgeable of all the practices of watersports. Your level of expertise no matter how high, you will always still have something to learn from us. Education is important to us because we are a small business where you truly matter, and we want to make sure we’re all mentors for you. One day, we believe you can be a mentor for others in your position. You will have a lot more responsibilities working this job than any other. We want to make sure you have “real world experience” education. Plus, the new experiences you will create in the most fun manner will stick with you for life.
The third reason to work for Lakeside Watersports is the lifestyle. If you’re truly interested in this job, it’s probably because you have a passion for watersports. You’re in luck, because we all do too! When you join our team, you’re joining friendships that will last you a lifetime. You will always be part of our team, and have a place at Lakeside Watersports. You being a part of the Lakeside team means you truly embody the watersports lifestyle. It’s our job here to share that love, and passion with our customers. We are here to show them why we do these sports, and how it’s important for your well-being to learn new skills like any of our disciplines. It’s our job to expose people to the best summer activity, and teach them the lifestyle you are now living!
We hope this short explanation gives you some detail into what you will learn being a part of the Lakeside Watersports Team. We are super excited to receive your application, and keep these three concepts in mind when filling out the application!
Employee Mission:
Here at Lakeside Watersports our employee mission is "We give our customers a boating experience they will never forget, and teach them skills they will never regret!"
Join our team of exceptional talent and help us maintain our 5-star reputation in 2025! At Lakeside Watersports, we are always looking for dedicated individuals to join our family and contribute to our legacy of outstanding service.
Become a part of something special and join us at Lakeside Watersports, where you will be valued as a team member and receive the support and resources you need to succeed.
Job Responsibilities:
Boat Driver/Watersports Instructor
This position entails working as a professional watersports boat driver and expert watersports instructor for groups of up to 10 passengers at a time. This individual will welcome guests, get them safely onto the boat, and navigate the heavily trafficked waterways of Candlewood Lake, returning the customers to the dock on time. Ideal candidates have many hours of experience driving and docking high-end inboard boats, have a boating certificate in CT and maintain First Aid & CPR Training. This position is seasonal with an agreed upon end date, and operates on an hourly pay schedule. Full-time and part-time positions available.
Deckhand/Spotter
This position acts as the driver’s second set of eyes and ears while out on the water. This individual will welcome guests, assigns proper safety equipment for all guests, help usher customers onto the boat safely, and helps spot other boaters and hazards while out on the water. Deckhand/Spotters will also help with the driver/instructor rope management, equipment preparation, and docking. There will also be opportunities for deckhands/spotters to help instruct groups and individuals learn how to perform watersports properly and safely. Ideal candidates are reliable, responsible, have great communication skills and have a passion for being out on the water. This position is seasonal with an agreed upon end date, and operates on an hourly pay schedule. Full-time and part-time positions available.
Greeter
This position is crucial to the first physical encounter with the customers, and greeting them upon arrival. Your job is to get the next group going out on the boat ready, and prepared! You assist in the transfer of customers to the Driver / Spotter, and answer any questions they may have before experience. The position will have you intercept customer at end of lesson too to secure that everything went well, and lesson is paid for in full. The Greeter also answers the phone in downtime to answer any generic questions a customer may have calling into us for some information (Directions, Pricing, Suggestions, Etc.). The job is also to help plan the day for the Driver / Spotter so everything moves smoothly in giving our customers a high-end experience!
CONNOR’S ASSISTANT
Job Summary:
The Assistant performs secretarial and administrative duties in support of Lakeside Watersports President / Owner. Responsible for managing phones, mail, scheduling, filing and general office management.
Job Description:
- 40 hour work week – 9:00 AM to 5:00 PM EST Thursday-Monday.
- Salary based position based on experience – Paid weekly
- Seasonal Job: May 1st to September 1st 2025
- Remote or Physical location work (Prefer physical) – Part of Lakeside Watersports Team (Wednesday sessions)
Job Responsibilities:
Training from Connor directly
Answering specific Calls & Emails
Communication with Greeters (Physical at Kiosk)
Salesforce Environment
Task Document
Tasks for Connor, and from Connor
Key Updates / Changes
Working with Business Manager
Run errands as requested (Physical)
Free time
Communicating with Priority Customers
Tracking tips
Connor’s Assistant Qualifications:
Relative experience of assistance
Proactive approach to problem solving
Strong Time Management & Organizational skills
Tech-savy and experienced with word processing and Gmail
Active listening and good communication skills
Strong interpersonal skills
General Qualifications:
Available to work between May and October 2025
CPR and First Aid Certified. All applicants must show current updated certification before employment.
At least 16 years of age by date of employment
Licensed Boater (All applicants for Boat Driver/Watersports Instructor will be asked to present a copy of their current boating license. For Deckhand/Spotter applicants, this is not a requirement but highly recommended)
Demonstrates passion for watersports, boating, and teaching others
Experience spending time in and around boats, specifically high-performance wake boats
Understands premium service and what it means to exceed customer expectations
Fantastic communications skills, both with customers and with colleagues/crew members
Prioritizes a safely executed customer experience
Experience taking payment in many different forms; cash wrap, mobile card terminal, cash, etc.
Organized and punctual. Ability to stay on schedule is paramount.
Can-do, positive attitude and willingness to work on a boat in the sun for multiple hours
Preferred Qualifications:
Watersports enthusiast, someone who enjoys watersports as a pastime/hobby
Candlewood Lake knowledge and ability to navigate the entire lake
Knowledge of boating and the mechanical workings of high-end wakeboard and waterski boats