Jason K. Cupp, CLP
President and CEO, Account Manager

Jason is our lead Account Manager, working closely with many of our clients, helping to develop relationships focused on key service areas. His love and passion for helping clients realize their dream property allows him to work closely with a Landscape Designer/Project Manger to execute on behalf of the client.

Jason also serves the firm as President and Chief Executive Officer. In this global-vision leadership position, he focuses on the strategic growth initiatives, the sales and marketing plan, and representing Highland Outdoor in the marketplace and beyond.

Jason is instrumental in our affiliation with the Professional Landcare Network (PLANET). In 2001, he successfully completed the Certified Landscape Professional (CLP) exam. He is one of a few in the Kansas City area with this designation. In May 2008, Jason will begin a year of serving PLANET as President. PLANET is the largest Landcare trade association in North America. Also, his various industry service has included: being involved in the design of a memorial park near Ground Zero in New York City, NY; a member of the Board of Directors of PLANET; and a founding Member of the International Certification Council and the International Liaison Committee, representing Certification Programs between the United States and Canada.

In 2006, Jason successfully completed courses to become a Certified Kolbe Consultant, a conative index that our firm has used extensively to align their teams for maximum synergy, balance and energy.

In his spare time, Jason is involved in many volunteer boards, including Young Life Chicagoland Region, and Reconnect Resources Kansas City. When time allows, he enjoys spending time with friends and family, traveling extensively, watching baseball and basketball games, specifically the Chicago Cubs and the Kansas Jayhawks.

Please visit Jasons LinkedIn Profile Here

Mitch Benjamin
Landscape Designer/Project Manager

Mitch serves clients as a Landscape Designer and Project Manager. With a degree in Horticulture and Landscape Design from Iowa State University, Mitch possesses skills and education to creatively deliver client expectations. Mitch has veteran experience in the landscape and design/build industry, having been involved in the green industry since age 16. Mitch’s involvement in the sales and design process is the core of assuring projects are delivered to the client as they are designed. Mitch specializes in communicating extensively with his clients, and takes pride in offering creative and efficient designs to each of his customers. In his spare time, Mitch enjoys sports, working outdoors, cars, and spending time with his wife, Shannon and son, Graden.

David Rowan
Landscape Designer/Project Manager

David Rowan brings experience and knowledge to the Highland Outdoors’ landscape team, with particular interest in natural horticultural landscape design and installation and native plant restoration projects.

David has served in a wide variety of roles within the green industry, from a groundskeeper at Eagle Knoll Golf Course in Hartsburg, Missouri to landscape designer of a multi-million dollar design build firm in Saint Louis, MO and many field installation positions in his edification.

David holds a bachelor’s of Science in Horticulture and Landscape Design from Kansas State University, and is a member of the Pi Alpha Xi National Honors Society for Landscape Horticulture. As a student at KSU, David attended a horticultural tour of Holland to study Dutch landscape Architecture and floral production, which included tours of the famous Hetloo Palace, Tropenburg Arboretum, and The Floriade, the Netherlands’ flower exposition that happens once ever ten years. David also was a participant for KSU in the Associated Landscape Contractors of America (ALCA), now know as PLANET, Student Career Days where he help his team place 11th of 54 teams student teams across the country in only their third appearance of this prestigious event for Green Industry students.

As a Professional, David was selected to attend the American Nurserymen & Landscapers Association (ANLA) annual Management Clinic in Both 2003 and 2005 as a scholarship recipient. David co-designed a landscape mater plan for a “Wild Times” Interactive ADA/Dementia-accessible Garden at the Heisinger Home nursing care facility in Jefferson City, which planned to bring the residents and their families together in a natural landscape setting on the bluffs of the Missouri River.

David is studying to become a Certified Landscape Professional (CLP), through PLANET.

In his free time David enjoys spending time with his family and friends at his family’s recreational farm, playing golf, and bird hunting with his German Shorthair Pointer.

Rich Clark, COLP, ISA Certified Arborist
Landscape Maintenance Manager / Account Representative

Rich serves Highland Outdoor clients by heading up the Landscape Maintenance Division. He is also the lead Account Manager for maintenance. Rich is a Certified Ornamental Landscape Professional (COLP), a Certification of the Professional Landcare Network (PLANET), and is an International Society of Arboriculture (ISA) Certified Arborist. With Rich’s 14 years in the green industry, he has an unprecedented knowledge and value to clients – ranging from turf to landscape to trees. Rich has owned his own tree and landscape company as well as has taken care of half of a 200+ acre finely manicured world headquarters of a Fortune 500 company located in Kansas City. Rich's experience and knowledge gives him a comprehensive approach to caring for clients’ landscape. Rich prides himself as comprehensively communicating with clients about their exterior living space, taking into consideration the home itself, the hardscapes, the landscape and the plants in it, as well the trees and the turf to assure clients properties look and feel its best from a horticulture standpoint.

In his spare time, Rich loves to spend it with his wife and two girls. Rich's hobbies include judo and climbing trees.

Abby Smith
Executive Assistant

Abby is a native of Kansas City. She is someone who is friendly, professional, helpful and most importantly, organized. With her job she is responsible for the overall administrative management of the office our President and CEO, Jason Cupp. As his Executive Assistant, her duties include, but not limited to, coordinating and tracking the schedule, travel requirements, activities, and project responsibilities.

Abby resides in Lenexa, Kansas. She is currently pursuing her degree in Business. In her free time she enjoys spending time with family and friends, sight seeing around beautiful downtown Kansas City, and of course supporting the KC Chiefs and Royals. And someday, hopes to travel.

Natasha Gabbert
Office / Sales Manager

Natasha is likely one of the friendly voices you’ll hear when you call the Highland Outdoor offices. She coordinates many facets of our office as Office and Sales Manager, and is one of the primary communicators with clients and vendors. Her focus on a smooth-running office is a huge benefit to the Management Team, so they can focus on client interaction on a daily basis in the field. Natasha is currently attending Ottawa University to complete her bachelor’s in Business and Marketing.

In her spare time she enjoys spending time with her family and friends, cooking, and working out. She also enjoys playing with her 3 dogs and going on an annual missions trip to Panama. She is an avid Chiefs fan, attends Life Church in Olathe, and currently resides in Osawatomie, KS.