Leadership Team

Tom Ostrom founded Encore Management and Development in 2001 with a desire to improve older Americans’ lives by bringing a new, innovative approach to senior housing. Since then, he has overseen the company’s successful portfolio growth through acquiring and developing properties.

Today, the Encore portfolio has 43 communities, nearly 2,000 residents, and 1,600 employees. Before starting Encore, Tom was the Senior Vice President at a large national senior housing operator.  A serial entrepreneur, Tom founded more than three dozen companies in and outside the senior housing industry. Tom graduated from Harvard College with a degree in Economics.

Tom lives in Chicago with his wife of 20 years, their two children, and one very lazy dog.

Fun Fact: Tom has 50 first cousins!

First Job: His first job was salting country hams.

Roth has been in the hospitality and seniors housing industry for over 35 years. He worked his way through Valdosta State University as a server and receptionist at a hotel while earning a bachelor’s degree in Management and Marketing. After graduating from college, Roth went into the hotel industry, then transferred his hospitality experience to senior living where he found his passion serving seniors in leadership positions such as Executive Director and Regional Director of Operations. As Chief Operating Officer since the inception of Encore Senior Living, Roth helped build the company’s inclusive, family-oriented, diverse and dynamic culture.

Originally from Live Oak, FL, Roth divides his time between Oak Park and Galena, IL with his partner Brad.

Fun Fact: Roth is a 5th generation Floridian and grew up on a 3,000-acre working ranch in North Florida – The Florida Sheriff’s Boys Ranch in Live Oak, FL.

First Job: Washing dishes and operating the potato peeling machine at the Boys Ranch at age 10.

Barbara has served in the Senior Living industry for over 20 years. Her journey began with a single site continuing care retirement community that fueled her passion to serve older adults.

Barbara has a diverse background and skillset having held consulting, operational, and Chief Financial Officer roles with multi-campus senior living providers throughout the Midwest. She maintains the highest ethical standards and prides herself on having partnered with CEOs to complete campus development and expansions, debt refinancing, and restructure operations.

Barbara holds a bachelor’s degree in business administration with a major in public accounting from Loyola University of Chicago and received her CPA from the University of Illinois.

Barbara recently became an empty nester and fled the suburbs for Chicago. She now enjoys morning runs along the lakefront, a walk to Wrigley for a Cubs game, and an occasional game night with her three children.

Fun Fact: Barbara worked her way through college as a bank teller. One day, a young rookie Chicago Blackhawk player stepped up to the teller window with his first paycheck for deposit.  He later went on to be one of hockey’s greats and was named to the Hockey Hall of Fame.

First Job: Barbara’s first job was dipping ice cream at Cock Robin, a local ice cream parlor restaurant chain famous for their “One-in-a-Million” shakes. After the first month, she was known as the fastest dipper.

Lindsey has had a successful career in the Seniors Housing industry over the past 15 years. She has a strong passion for sales and marketing and the impact that a positive sales culture within a company has on its success. She grew her skill set as a sales professional at the community level, which set a solid foundation for understanding the needs within the community.

Prior to joining Encore, Lindsey served as the Vice President of Sales Training and Talent Development for a large seniors housing provider. She is an integral contributor to a seniors housing leadership team and embraces the notion that in order to have a positive company culture, its leaders need to lead by example. Lindsey holds a bachelor’s degree in Psychology and a master’s degree in Sociology/Gerontology.

Lindsey lives in Oak Park, IL just outside of Chicago, with her husband Brian and their two children, Adeline and Kevin. In her free time, she enjoys exercising and lots of family time!

Fun Fact: Her first job in a senior living community was as a server in high school. She loved it so much that she persuaded all her friends to come and work with her.

First Job: While Lindsey babysat from the about the age of 10, her first paid job was in a dry cleaner!

Jennifer has worked in the seniors housing industry for the majority of her career. She has over 22 years of experience starting as a caregiver and evolving to various leadership roles. She is currently the Vice President of Human Resources for Encore. Jennifer has her bachelor’s degree in Psychology, Human Resources and Organizational Leadership.

Jennifer lives in Sherwood, WI with her husband Gary and their three children, Miya, Nora and Callen. They enjoy doing things together as a family and finding ways to make each other laugh. Outdoor activities such as skiing, snowshoeing, kayaking and camping are frequent weekend activities.

Fun Fact: Jennifer coached a youth soccer team for seven years and took a hiatus after her first child was born. At nine-months pregnant with her son, she discovered her daughter’s soccer team needed a volunteer coach, so she signed herself up. She coached a game, and her son was born the next day!

First Job: Jennifer’s first job was at Discovery Zone, an entertainment facility for young children.

Fun Fact: While vacationing in Jamaica several years ago, Leslie jumped off a cliff at Rick’s Café in Negril.

First Job:Leslie’s first job was as a front counter server at Kentucky Fried Chicken restaurant.

Michael has over a decade of experience serving residents in the Senior Living industry. His journey began as a care advisor helping seniors and their families find solutions to long-term care needs. In this role, he quickly learned he had a passion for enabling seniors to continue to live active and fulfilling lives within their communities.  Through the course of his career, Michael’s roles have ranged from marketing and sales positions to executive leadership positions.  Michael is a servant leader who strives to empower his teams to achieve success but does not hesitate to roll up his sleeves and pitch in where needed.   Prior to joining Encore, Michael served as a Regional Vice President for a large Senior Living provider and was a key contributor to its success.

Michael lives in the Indianapolis, Indiana area with his wife, Julie. In his free time, you will find him getting as much wind therapy on his Harley Davidson as possible, doing volunteer work with abused children, or cheering on his favorite sports team, the St. Louis Blues.

Fun Fact: In 2021, Michael earned his first patch from a popular distance riding association for riding over 1000 miles from Indianapolis to Orlando in less than 24 hours!

First Job: Michael’s first job was as a kid helping with his family’s business which owned and maintained cemeteries in southeast Texas. His first paying job was on a sod farm in St. Louis, MO cutting and laying sod for various customers.