Meet the Team

Meet the Watermark Team

Debbie Gosselin, President

Joined Watermark in College

What is your favorite Watermark product and why?

This is like asking which of your children is your favorite. Each of Watermark’s products is unique, distinct, and supports our brand essence statement. They’re all great!

Have you ever held any other positions at Watermark?

I started out as a crew member in college; became the bookkeeper in the early 1980’s, and President in the 1990’s. In 1999 when I purchased the tour and charter boat business from my father, I became the owner.

What is your favorite Watermark memory?

There are too many, but my favorite continuing experience is meeting and working with so many wonderful young people. They remind me that the future is bright.


Heather Skipper, Director of Guide Operations

Joined Watermark February 2008. Plus, Heather worked for Watermark during summers while in college.

What is your favorite Watermark product and why?

My favorite Watermark product is the Day on the Bay to St. Michaels. It is the most relaxing, laid back, and excellent way to cross the bay to the small port town of St. Michaels. One hidden gem on the cruise over in the morning is the local donuts that are provided!

Have you ever held any other positions at Watermark?

Yes, I was the Water Ops Assistant during my summers in college. I have also bartended, sold tickets, and worked in the sales office during my college years. I have also jumped in and live narrated the Miss Anne cruise way back when!

What was your first job?

Jeepers Junior: Fun, Food and a Monkey in Fairfax, VA!I was a teenager in High School and I learned to be a cashier and cook, then a Manager.


Ginny Mininger, Vessel Operations Manager

Joined Watermark Fall 2011.

What is your favorite Watermark product and why?

City Lights Cruise! It’s such a magical way to see the city of Baltimore and there’s great music.

Have you ever held any other positions at Watermark?

One time I planked for 2 minutes. I also managed operations in Baltimore, then Annapolis, and now I am responsible for the operations in both locations.

What is your favorite Watermark memory?

Seeing our Captain pull Harbor Queen into City Dock on a rainy day with 250 kids doing the Harlem Shake. Somehow, even on rainy days we all still have a blast.


Dave Lewald, General Manager of Vessel Activities

Joined Watermark 2016


April O’Brien, Director of Sales and Marketing

Joined Watermark January 2011

What is your favorite Watermark product and why?

Too hard to choose! I grew up on the water so any cruise is great! But I studied history so I also enjoy the land side too. Parties are fun so private charters?It’s the variety that works for me…and why I enjoy promoting and selling all our products and services.

Outside of Watermark, what is your favorite thing to do in the Chesapeake Bay area?

On the water. Usually out on the South River with hubby Paul and our golden retriever Lou. In chillier months we love exploring the Bay’s shorelines and hidden places in and around Annapolis. Never a dull moment!

If you could trade jobs for a day with anyone at Watermark, who would it be and why?

The position really doesn’t exist as a separate “job” but I’d love to answer all the questions from guests helping them with cruises, walking tours and events in Annapolis and Baltimore. Head Watermark Concierge?


Chip Johnson, Comptroller









Rick Flamand, Annapolis Vessel Operations Manager

Joined Watermark February 2017


Zach Gibbons, Baltimore Vessel Operations Manager

Joined Watermark 2010

What is your favorite Watermark product and why?

My favorite Watermark product is the Baltimore Firework cruises on the 4th of July. Baltimore always puts on an impressive display and Watermark's part in the event puts you in the best viewing area.

Have you ever held any other positions at Watermark?

Yes. I started here as a crew member straight out of High School.

Outside of Watermark, what is your favorite thing to do in the Chesapeake Bay area?

I love adrenaline sports and being outside. Boating in the Severn River with my family and friends is also one of my favorite things to do.



“Mac” McAleer, Director of the Fleet

Joined Watermark March 2015

What is your favorite Watermark product and why?

The employees! In all my years of working, I have never met such a great group of people...from the Management, Captains, Crew, Sales, and Operations...I haven’t seen such a professional group of individuals, that have great personalities, and go out of their way to make sure our customers have such a great experience.

What was your first job?

I was given a very large glove that went all the way up to my shoulder. Little did I know I had to reach inside the Microphor holding tank and unclog a drain! People laughed so I guess I passed the test.

Outside of Watermark, what is your favorite thing to do in the Chesapeake Bay area?

Sailing and racing my boat.


Taylor Kshimetski, Private Yacht Charter Sales and Event Planner

Joined Watermark February 2012

What is your favorite Watermark product and why?

I love the selection of private yachts and vessels that are available for hosting events on the water. There’s no better place to celebrate any and all occasions than on the water and truly, no decorations are required!

What was your first job?

My first job was working in the fields on the farm that I grew up on. I love, and still do, the feel of fresh turned dirt. As part of my responsibilities, I also provided snacks and the noon-day meals for the hired help when it was harvest time. I didn’t always care for the hot Georgia sunshine but I do cherish the memories and the friendships that were formed during the season.

Outside of Watermark, what is your favorite thing to do in the Chesapeake Bay area?

I love sitting on the docks while sipping on a cocktail, having light conversations with friends and soaking up the amazing views!


Missy Blevins, Private Yacht Charter Sales and Event Planner

Joined Watermark 2014. Previously worked with Watermark as a guide.

What is your favorite Watermark product and why?

I really enjoy helping families with special celebrations (wedding, anniversaries, birthdays) on private charters.It’s great to see the joy they express when everything comes together as planned.

What was your first job?

I mucked stalls, groomed horses and babysat at my riding instructor’s farm in exchange for riding lessons.

Have you ever held any other positions at Watermark?

I was a tour guide for approximately 8 years before joining the charter sales team. I thoroughly enjoyed giving tours to the many school children and visitors to the area.


Claudette McDonald, Group Sales Specialist

Joined Watermark 2000 as a tour guide.

Have you ever held any other positions at Watermark?

I tour guided, and have been the clothing designer and seamstress for 15 years (yikes).

Outside of Watermark, what is your favorite thing to do in the Chesapeake Bay area?

I love touring vineyards with my family, taking my Golden Retrievers anywhere, spending time in the Mountains – reminds me of home.

What is your favorite Watermark product and why?

I have lots of favorites – the Day on the Bay makes me feel like I am on vacation, the new Time & Tides enhances all I thought I knew about the area and the Four Centuries Tour is still the best ambassador program for Annapolis.


Jennifer DeLancey, Group Sales Manager

Joined Watermark March 2012.

What was your first job?

My first job was as a camp counselor and I was also the Water Skiing Instructor and Program Director at the camp. The camp was an all-girls’ camp near Highlands North Carolina. It was in the mountains and a beautiful area.Great first job!

If you could trade jobs for a day with anyone at Watermark, who would it be and why?

I would like to be a Captain. I lived on a boat for 12 years that looked like Cabaret II and I miss being behind the wheel. I have also always wanted to be a Bartender!

What is your favorite Watermark product and why?

My favorite product at Watermark are any of the Cruises because I just love to be on the water!


Cindy Wells, Retail Program and Merchandise Manager

Joined Watermark December 2014

What is your favorite Watermark product and why?

WRNR Rockin’ River Cruise is my favorite because it is an intimate format for experiencing great music.

What is your favorite Watermark memory?

I liked going to WineFest in St. Michaels on Lady Sarah. It was cool and overcast but a lot of fun and the first time I had gone to St. Michaels via boat.

What was your first job?

Produce merchandiser in the Commissary (grocery store) on an American Communications Station in Germany where I lived with my family.


Mike Mathias, Director of Inventory

Joined Watermark in 2006

What is your favorite Watermark product and why?

The 40-minute Annapolis Harbor and USNA Cruise on Harbor Queen. The timing is just right – short and sweet – and it captures the history of Annapolis.

What was your first job?

I worked as a deckhand on a sportfishing boat.

Outside of Watermark, what is your favorite thing to do in the Chesapeake Bay area?

I do a lot of metal detecting on beaches and farmlands looking for Civil War relics and Colonial artifacts. I used to hunt in Patterson Park a lot and found many gold coins.


Katie Redmiles, Marketing Specialist

Joined Watermark February 2012

What is your favorite Watermark product and why?

I like the Four Centuries Walking Tour. I’ve learned so much about the city I call home by taking this tour and each time I’ve taken it, it’s been a different experience because every tour guide puts a personal spin on the tour. Great for locals and visitors!

What is your favorite Watermark memory?

Our tour guides were given a preview of the restored Old Senate Chamber by the historians who worked on the restoration. I was fortunate to attend as well and learn about the project and the historical significance of the room. When the room was later opened to the public by Governor Hogan, Watermark was given notice and I was there to see the official opening.

What was your first job?

I worked concessions at the Bowie Baysox Stadium. I learned customer service skills before I even had my driver’s license and enjoyed an unlimited supply of cheese fries.


Maggie Flamand, Customer Service Coordinator

Joined Watermark April 2015

What is your favorite Watermark product and why?

I love riding the Yachts!Everything is better when you’re on the water!

What is your favorite Watermark memory?

Blue Angels Day…riding the yachts over to City Dock…seeing all the people, helping with the logistics of getting everyone where they needed to be.

If you could trade jobs for a day with anyone at Watermark, who would it be and why?

I’d like to trade jobs with Ginny and work Operations because of my Blue Angels Day experience. I like being busy and enjoy customer service.