Blog Post

Want to work at Osprey’s Echo Sea Kayaking?

by | May 29, 2025

Osprey’s Echo Sea Kayaking is clearly a seasonal business.  There’s not much demand for kayaking between, say, November and April.  This is why you see Will head to a ski mountain and Mike and Dale start to travel.

The first couple of years, the business consisted of Will, Mike and Dale with periodic valuable help and support from his siblings, Katie, Sarah and Jack.  It became apparent of course that we’d need more help.  The nature of the business is that we need to recruit each year, hiring people who are interested in a great summer job, but with a hope that we will attract someone who would like to return year after year.

We think a lot about the type of people we’d like to attract to work with us.  First and foremost is the importance of fitting in with our team, being attracted to the culture and truly enjoying the work. Our customer relationships are the most important thing we have, and the “family-run” vibe of the company is attractive to many.  We need people who will enjoy working with our customers, will have a smile on their face and will enjoy Surrey and Gimli, our loveable dogs who are the chief meeter-greeters for the company!

We need a variety of skills at the company.  We need help on the waterfront.  This role includes everything from greeting customers to hauling and servicing the boats, to maintaining them properly. It is an outdoor job, involving both physical labor and good customer relationship skills.  We have found that it’s a great job for either a local high schooler or a college student.  We had one college student who worked with us on the waterfront for two years.   He did not aspire to be a licensed guide, but he was a real part of the family at Osprey’s Echo.  He enjoyed the physicality of handling the boats, was detail-oriented and redesigned some of our processes when it came to managing the gear, and he was always a smiling face for our customers.

Young man holding kayak on shore

The other important role is a licensed sea kayak guide, Will is a licensed guide, Wilderness First Responder and an ACA level 3 instructor.   He spends up to 10 hours a day on the water, and he loves it.  He loves paddling, but even more he loves treating customers to the enjoyment of exploring our archipelago and learning all about it.  When we have a second or third guide available we have flexibility – we can run more tours, take more customers out, and launch new products.    What does it take to become a sea kayak guide at Osprey’s Echo?

Firstly, you need to pass the Maine Guide exam for sea kayaking.   We will admit that it’s a non-trivial process as the state of Maine is more rigorous than any other in the nation when it comes to ensuring our guides are qualified. Sea kayak guides will be tested on navigation skills, safety and paddle technique, even knowledge of the local birds and animals.  We have helped four people pass the exam already so we know we can help with the process, but it does require commitment. Candidates can start working at OESK in May, start studying for the exam, take advantage of all the materials that Will has accumulated over the years, enjoy the opportunity to attend a class we host, and book a date to take the exam with the Department of Inland Fisheries in Augusta.  Once you have the license, you are permitted to take customers out on the water! I probably should note that you don’t have to work for us to take advantage of this excellent training.

In parallel to preparing for the license exam, we will help you learn all about paddling in Stonington, how to enjoy being a part of the OESK team and even some of the stories we tell our customers out on the water.  We like to offer an educational experience as much as a physical (paddling) one.  We talk about the history of the island, the lobster industry, and interesting facts about the birds, seals, porpoises that we will see.  Our customers enjoy this.  We are also ‘ambassadors’ for the island, or as we say “guides on and off the water”.  We are always keen to help our customers with their questions about where to eat, where the best hiking is, and what other wonderful things there are to do on this island (see our earlier post on this topic!).  This is the full OESK experience and we want all of our staff to embrace it.

Finally, there are opportunities to learn what it takes to start and run a small business.   Guiding and waterfront support are vitally important – they are the product and service we provide. However, there is a lot more to the business behind the scenes – managing our booking system, developing new marketing ideas and campaigns, managing our social media presence, and other important back office topics.   Some of our staff have really enjoyed dipping into these topics, learning the ins and outs of running a small business and helping us a great deal along the way.

Last summer, Maggie McCrostie and Delphine Demaisy – college students – passed their guide exam, became excellent guides, helped us run the business and enjoyed a wonderful summer.  We are looking forward to welcoming new staff members this year.

Working with Osprey’s Echo Sea Kayaking is a wonderful summer job.  Deer Isle is magical – its beauty, culture and plethora of activities will stay with you after you have moved on.  Whether you spend one summer with us, or make it an annual commitment, our experience suggests that you won’t regret it! 

Group of individuals in front of Osprey's Echo Sea Kayaking Sign

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