About Us

Jim Dean | President & Sales Professional

I grew up in NW New Jersey on a glacier lake where we spent every summer sailing, canoeing, and making boats out of anything that floated. When I was 20, my stepfather and mother bought a 42’ Post that they kept in Bay Head, NJ. This took my boating adventures to the next level, to say the least! Every weekend, we would run out of the Manasquan inlet and enjoy taking a cruise and fishing! When I received my Bachelor of Science degree from Centenary University in 1992, I went to work in the Corporate World. My first job was Bell Atlantic Mobile in NJ. I spent about a year there and had an opportunity to transfer to the Annapolis Sales team. This is when I was introduced to the Chesapeake Bay boating scene! The first thing I did was buy a boat and explore the Bay on the weekends. I spent the next 10+ years in sales driving around the beltway for Bell Atlantic Mobile, MCI, Quest, Microsoft, and Net App.

In 2006, upon the arrival of my first of three boys, I decided to make my dream a reality to start my own company. I combined my love of boats, sales and service to create Deans Yacht Services, Inc. We are currently are in our 15th year, and are a full service boat and yacht maintenance company in the Annapolis and surrounding areas. Dean’s Yacht Services, Inc. believes that personal leadership and involvement gets things done in exceptional ways.
When I decided to become a Broker and pursue a Yacht Sales Company, I wanted to find one that believed in service first, sales second. Since customer service is the driving force behind Dean’s, I felt I was missing the ability to help purchase and sell vessels for my customers.

As for my personal life, My wife and I, and our three boys, a dog and two cats live on Kent Island. We are very busy with sports on the weekends, but always find time to get out on the water, go surf fishing down on Assateague Island and skiing in the winter! We truly love Kent Island and the lifestyle that goes along with it!!

Jim Dean
Cell: 410-353-8888
Email: [email protected]

Lisa Dean | Vice President & Sales Professional

Spending the last 25 years with my husband, Jim, I grew to love the Chesapeake Bay and all that it has to offer.  Many of our most special times were on a boat!  My role with the Company is to make sure everyone is aware of the amount of sales support, advisement, management etc that Dean Yacht Company brings to our customers on a daily basis.  See you on the water!

Email: [email protected]

Dailey Tipton | Sales Professional

After a successful corporate career and many years of yachting Dailey has joined Dean Yacht Company in July 2023. Starting off, he worked as a rigger to fund his way through college and gained a Navy Scholarship, leading flight school and eight years of service including the Gulf War. He then spent 25+ years in High Tech and Sustainability field, all the while pursuing his passions for the water and yachting.

He has many years of experience as a big boat bowman on offshore racing yachts on both East, West coasts and Caribbean, then migrated to the Chesapeake in the 90’s where his interest split to large power boats and sailing. Dailey is a skilled mechanic, rigger, fiberglass/carbon fiber fabrication and repair, and marine wood working. His passion for the yachting industry is infectious.

In personal life, Dailey and his wife Jessica own a Mochi Craft 44 Dolphin they keep in the Northern Chesapeake and race sailboats competitively out of Annapolis. Dailey and Jessica’s have two grown children (Nate married to Kacie, and Leah married to Shane) and two grandchildren. Dailey is a competitive athlete in open water swimming, long distance trail running and the continued focus on racing sailboats.

Dailey Tipton
Cell: 484-947-9334
Email: [email protected]

Peter Pupshis | Sales Professional

After a successful corporate career as a Certified Public Accountant and many years of yachting Pete joined Dean Yacht Company in August 2023. He spent his early years fishing and crabbing the Chesapeake Bay and its tributaries. His first boat was a 1972 Boston Whaler and owned and operated may more sense that time. In 2018. Pete obtained his U.S. Coast Guard Operator of Uninspected Passenger Vessel (OUPV) and later obtained his 25ton Masters with a Towing endorsement. He then spent 25+ years in public accounting, all the while pursuing his passions for the water and yachting.

He has many years of experience as a charter boat captain in and around Ocean City Maryland both offshore and coast bays.  In addition, he spends time on the water teaching safe boating as a certified safe boating instructor.  He also is a level one certified Yamaha technician.  His passion for the yachting industry is infectious.

In personal life, Pete and his wife Cheryl own a center console Sportsman that they keep in Ocean City and the Chester River. Pete and Cheryl have two grown children (Alec and Cameron). Pete is an avid fisherman and spends as much time offshore chasing Tuna and Mahi Mahi.

Peter Pupshis
Cell: 443-243-6930
Email: [email protected]

Teressa Penland | Comptroller

Teressa is the eyes and ears of the financial health of Dean Yacht Company.  She brings a over 30+ years in the Financial, accounting, taxes and insurance industry.  She manages day-to-day financials as well as long term financial decisions.

Tom Flint | IT Manager

Tom is responsible for making sure Dean Yacht Company’s website, social media platforms, as well as their technology partners are in place.  Tom keeps our platforms nimble which gives us the ability to apply all new technologies in a timely manner to help give our clients a great experience whether on a social media platform, or on our website.