Work for Portland Paddle in 2019

Join Us as a Manager, Guide or Shore Staffer

UPDATE 5/8/19: We have finished hiring for the 2019 season. However, feel free to reach out if you are interested in connecting about joining our team part-time or in the future — especially if you are a licensed Maine guide.

Portland Paddle is staffed by a talented team of folks who are passionate about paddling. Many of our staff members from past years return every summer, but we're also seeking new members of our team for the 2018 paddling season, which starts in late May. 

We're hiring for these positions (scroll down for complete descriptions) for our 2019 season: 

The Portland Paddle Staff

The Portland Paddle Staff

SHORE STAFF: This is our entry-level position that involves supporting our sea kayak and paddleboard rentals and trips. 

SITE SUPERVISOR: This position is similar to the core staff job, but it also involves a leadership role overseeing operations at our main site. 

OPERATIONS MANAGER:  This is a position for someone who has management and outdoor leadership experience and is interested in taking on a major leadership role in coordinating our operations and supervising staff. 


SEA KAYAK GUIDE: You must have a valid sea kayak guide license from the state of Maine or be prepared to take our guide training class in May (or a guide class offered by another company). 

PADDLEBOARDING INSTRUCTOR: You must have the relevant guide license from the state of Maine or be prepared to take our guide training class in May (or a guide class offered by another company). 


1.  Scroll down this page and read the relevant job descriptions. Decide which position is the best fit for you. Also take a look at our website so you understand a bit more about us and what we do.

2.  Complete the online application by clicking the button below: 

3. Email your resume to us.  If you have additional information you'd like to share with us or questions you'd like to ask feel free to include that in your email as well.

4. Applications will be accepted on a rolling basis, but we intend to make most offers by mid-March, 2018. Some positions may not be available after March. However, we're always happy to hear from qualified folks interested in working with us, and we are always in need of licensed sea kayak guides. Feel free to reach out anytime. 


Giving a quick lesson on the parts of a sea kayak

Giving a quick lesson on the parts of a sea kayak

This is the core staff position at Portland Paddle. We call it "shore staff" because most of the work is done on land as opposed to the on-water work of our guides. This position involves a wide range of tasks, but your basic job is to support our sea kayak and paddleboard rentals, tours and lessons at the East End Beach. If you'd like to spend the summer outdoors and you're interested in paddlesports, this could be a great job for you. You'd be joining a terrific team that includes staff who have been with us for several years. This job requires hard work and commitment. It also provides lots of opportunities to learn new skills, meet interesting people from all over the world and become well-acquainted with the beauty of Casco Bay. 

This is a full-time seasonal position (30-40 hours/week)  that lasts from late May through August, with the option of taking more work through September and October. Scheduling is somewhat flexible, but working many weekends and evenings is essential. Our staff spends much of its time interacting with customers, so we are looking for individuals who are prepared to be friendly and communicate effectively. The job also requires lifting and carrying loaded kayaks every day, so you should be generally fit and capable of carrying a fairly heavy boat with assistance. This is a very active job that can be both physically and mentally challenging. 

What the job entails:

  • Helping customers rent from our fleet of kayaks & stand-up paddleboards (SUPS).

  • Offering basic safety and skills tips to customers.

  • Taking reservations, in-person and over the phone, for rentals and tours.

  • Lots of carrying and loading kayaks and SUPs (with help).

  • Assisting guides on tours and lessons.

  • Making important judgment calls regarding safety (for example, turning away customers based on an assessment of weather conditions).

  • Keeping our shop clean and organized.


  • Easy-going, with a sense of humor.

  • Interested in spending lots of time outdoors.

  • Able to help carry kayaks and assist with other physically demanding tasks.

  • Available from late May through August, and September if possible.

  • Kayaking and/or paddleboarding skills are not necessary, but candidates should be enthusiastic about learning and passing on knowledge of paddlesports to customers.

  • First aid or lifeguard certification is preferred (if you don't have First Aid certification you would need to get certified before starting the job).


  • Starting at $12.00 per hour, with significantly higher rates possible for those with relevant experience.

  • Free use of kayaks and SUPs (with advance notice).

  • Pro discounts on outdoor gear.

  • Opportunities to develop paddling skills through free courses and training sessions.


We are seeking a supervisor this year who can support the operations manager and the owner with the leadership of the business. The job will involve everything included in the description of the "shore staff" position (see above), but the site coordinator will also have the following responsibilities:

  • Assisting with staff training and staff communications.

  • Assisting with staff scheduling.

  • Managing the Portland Paddle physical site to ensure a well-organized, attractive appearance that is visible to customers and the public.

  • Attending weekly meeting with the owner and operations manager.

  • Assisting with marketing through use of social media, blogging and other means.

  • Modeling strong customer service skills and outdoor leadership for the entire staff.


  • Customer service experience.

  • Experience working in a leadership position in the the outdoors industry.

  • Paddling experience (kayaking, canoeing, rafting or paddleboarding).

  • Should be comfortable using and/or learning to use various software programs and other technologies (online booking system, google drive, online scheduling, etc).

  • First aid certification preferred.


  • Starting at $15, with higher rates possible for those with relevant leadership and paddling experience

  • Free use of kayaks and SUPs (with advance notice).

  • Pro discounts on outdoor gear.

  • Opportunities to develop paddling skills through free courses and training sessions.


The Operations Manager (OM) is responsible for overseeing all aspects of Portland Paddle’s operations, in coordination with the owner and managers, from late May through September.

This is a full-time, seasonal position for someone with substantial professional experience in positions of leadership or management as well as significant experience in the outdoors industry, preferably with paddlesports or ocean-related activities. Ideally, the OM will have experience working as a sea kayaking or paddleboarding guide -- or have some similar experience. The OM will work closely with the owner and site coordinators and will be responsible for managing all staff and ensuring that all operations are running smoothly and efficiently. A top priority of the OM will be minimizing risk in all areas of the operations and promoting a safety-conscious culture among staff and with customers.

The job involves a diverse mix of tasks, including office work, customer service, management of staff and some manual labor.  Professional experience with graphic design, bookkeeping and/or marketing (social media promotion, advertising, etc.)  is also a plus, but not required.

The OM is a manager-level position that involves management duties, but Portland Paddle is a very small business and the OM should expect to spend a significant amount of their time on more basic tasks that are shared with all staff. These tasks include answering phones, cleaning kayaks, moving and organizing gear, opening & closing the shop and working with rental customers.

Portland Paddle’s operations are based out of a shipping container with limited space and access to electricity. The OM should be comfortable with an unconventional working environment that involves limited traditional office space and the need for flexibility and improvisation.

A Maine guide license is not required for this position, but candidates with a license are preferred. An OM with a guide license would spend some time guiding trips, mainly when other guides are unavailable. If a person without a guide license took this position they would be encouraged to complete the Maine guide testing process and become licensed. That said, it is not essential that the OM be a licensed guide.

The position extends from mid-May through mid-September, with the potential for part-time work earlier and later. Over time, the position could grow into a year-round job for the right person. 

Responsibilities include all those described above in the "shore staff" description above plus the following: 

  • Staff scheduling.

  • Assisting with staff training.

  • Managing reservations for tour, rental and lesson programs.

  • Maintaining and coordinating repairs of all Portland Paddle gear and equipment.

  • Ensuring that all staff policies are being implemented and followed.

  • Providing staff with clear instructions on a daily basis regarding specific tasks that need to be addressed

  • Ensuring that all customer phone calls, emails and online reservations are dealt with in a timely manner.


  • Negotiable and competitive. This position can be compensated by salary or hourly wage, depending on the candidate's circumstances and experience.

  • Free use of kayaks and SUPs (with advance notice).

  • Pro discounts on outdoor gear.

  • Opportunities to develop paddling skills through free courses and training sessions.


Guide image.jpg

We are looking for a registered guide to join our terrific team of trip leaders. You must have a guide license from the state of Maine to work as a guide for Portland Paddle.

If you do not have a guide license, you could enroll in our four-day guide training course that starts on May 19. If you passed the state guide exam and worked for Portland Paddle you could potentially qualify to be reimbursed for most of the course cost. 

Previous experience kayaking in Casco Bay is not required for this position but is a big plus. ACA–instructor certification is also a big plus (and it allows the candidate to teach our many lessons), but certification is not a requirement for the job.

 Portland Paddle offers a wide range of guided trips in Casco Bay. Take a look at the "guided trips" page of our website to see our list of offerings. New guides typically lead lots of Sunset Tours, Fort Gorges Tours and Half-Day Tours. There may also be opportunities to lead overnight trips. New guides go through a training and evaluation process and start off shadowing other guides before leading trips on their own.

 Scheduling is flexible for this position. The hours could be part-time or full-time, and we may be able to work around scheduling constraints (such as a regular day job). However, we prefer to hire a guide who is available to lead at least a couple dozen day trips throughout the 2018 season.

 Compensation: Negotiable, but competitive and tied to past experience and credentials.


We are looking for a paddleboarding instructor who is qualified to teach our SUP lessons. Portland Paddle offers a two-hour SUP lesson every Saturday and Sunday, and we often offer private lessons too. Most of our lessons are geared towards beginners, but we are interested in offering more advanced programming and guided trips also. We would love to find someone to join our team who is passionate about SUP and eager to share that passion with others.

 This is a part-time position that involves filling in occasional gaps in our staff schedule, though it could grow to a bigger commitment over time. Lessons typically take place during the weekends.

 Compensation: Negotiable, but competitive and tied to past experience and credentials.