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2017 Best Bosses

Celebrating Southwest Florida’s top leaders.



Not everyone is meant to lead, but everyone can be affected by a great leader. That is an individual who can inspire people to believe in themselves and matters around them. In the workplace, it’s someone who empowers staff to take pride in their positions and the company that employs them. Someone who lets workers know their ideas matter—and that they matter.

In order to recognize top leaders in our community, we asked readers to nominate their esteemed superiors for our Best Bosses story. We received more than 50 nominations of bosses who were highlighted for their kindness, support, strength and benevolence. The submissions were reviewed and voted upon by our panel of judges: Karen Anderson, vice president, HR & Technology/corporate compliance officer with Shell Point Retirement Community; Kelli Baxter, principal with Value Generation Partners; Anne Frazier, major gift officer with the Lee Health Foundation; and two Gulfshore Business staffers.

In the end, the following five bosses earned the top spots for their unwavering commitment to their teams. Please read on to learn what makes these leaders special in the eyes of their workers.

Education: Dr. Angela J. Pruitt

Chief Human Resources Officer, School District of Lee County

When Dr. Angela J. Pruitt assumed her role as chief human resources officer at the School District of Lee County in 2014, she held individual meetings with employees to hear their needs and concerns, and establish trust among them. Three years in she continues to build on that trust, strengthening internal relationships and the district’s human resources division overall.

“Employees consistently say they feel like they are part of a family and feel connected to one another and the division,” according to nominators and staff members Christine Christensen and Shellie Halstead. “Her leadership contributes to an overall sense of care for each other and a focus on what matters most.”

Pruitt’s dependable leadership style encourages the betterment of the school district, positively impacting student achievement in turn. She’s embraced a systematic and data-driven approach to set her division apart from others in the state of Florida, and focuses her service on staff, customers and stakeholders.

Pruitt has been involved in a number of national, statewide and regional endeavors, including Society for Human Resource Management, PACE Center for Girls, Project Management Institute, North American Association of Educational Negotiators, Florida Educational Negotiators, Lee Health Impact Initiative, Cape Coral Goldcoast Rotary Club, Lee County Educational Administrators, Florida Gulf Coast University College of Education and more.

She’s a proud mother of two sons, Mitchell and Wesley, and enjoys exercising at Orangetheory Fitness. 

Nonprofit: Sarah Owen

President and CEO, Southwest Florida Community Foundation

Sarah Owen is a collective leader who empowers her staff to make real and sustainable change within their region and lives.

Owen works to give each of her employees a good work/life balance based on their independent circumstances, trusting that they will bring their best game to the office when given the space to perform well in other aspects of their lives.

She’s known among her staff to be fearless, compassionate, intelligent and influential. “Sarah has been an incredible role model and has shown us what great leaders, especially women, can do in the community, and how much of a difference one can make,” says Caroline Rogers, the foundation’s vice president of development and communications.

She’s also “a master of her media,” caring deeply about people who do not have a voice and assisting them through the foundation, which supports community nonprofits and charitable causes.

Under Owen’s leadership, the foundation has become one of the largest funding organizations in the region. She continues to give back outside of the office by mentoring young girls and participating in speaking engagements. She’s the Florida delegate for the National Vision 20/20 Initiative, chair of the Community Foundations of Florida, a board member of the Southwest Florida Economic Development Alliance, and on the Healthy Lee Steering Committee. She enjoys writing and spending time with her family. 

Medical: Mike Ellis

CEO, Healthcare Network of Southwest Florida

Mike Ellis sets the tone for a collaborative spirit within the healthcare community. The Healthcare Network of Southwest Florida CEO believes in teamwork, rather than competition, and works tirelessly to get the right people in the room to generate solutions. “His leadership brings people together, and allows them to believe in their own ability to make change,” according to Steve Wheeler, the organization’s vice president of development.

Ellis’s passion and positivity influences employee morale, and he strives to work with each team member’s strengths, weaknesses, likes and dislikes, in order to draw the best from each individual. He also encourages self-care and camaraderie among workers. “Mike is humble and his modesty sets a tone of humility and strength that everyone else follows,” Wheeler says.

A former board member of Lee Health, Ellis currently serves on the Lee County Mosquito Control District board and Marieb College of Health & Human Services advisory board at Florida Gulf Coast University. He joined Healthcare Network as CEO in 2013 and has more than three decades of healthcare experience under his belt.

He is an avid Ohio State Buckeyes fan and has attained black belts in taekwondo and hapkido. He’s active in boating and environmental issues affecting Pine Island, where he resides, and is a master-licensed Coast Guard captain and scuba diver. Ellis also discovered a love of mountain climbing and all things Africa after he and other Naples community members participated in a Kilimanjaro for Kids climb fundraiser. The climb raised more than $400,000 for The Golisano Children’s Hospital of Southwest Florida. 

Large Company: Michael Wynn

President, Sunshine Ace Hardware

When you’re running a business with multiple locations and hundreds of workers, it’s easy to let employee satisfaction slip through the cracks. Michael Wynn, however, doesn’t let that happen. The Sunshine Ace Hardware president has implemented a number of programs and learning opportunities to keep 300-plus employees engaged, including a “future leaders” program, which identifies and trains future talent. Key management and staff members of the eight-location operation are also encouraged to build soft skills with the 11-week Dale Carnegie “Effective Communication and Human Relation Skills” course, and company leaders meet with associates each month to discuss goals, opportunities and concerns.

Each year, Wynn leads the business in a Team Appreciation Week that honors associates with daily events, food, prizes, games and raffles. Associates are also treated to company picnics, tailgate parties and holi- day gatherings. Then there are the smaller routines, like ending the day with a game of charades or starting the morning off with a bad joke—a ritual that began in one store and filtered through the others.

The activities sound typical of family gatherings, which makes sense, because Sunshine Ace is family-owned (Wynn’s grandfather, Don, founded the company). Wynn works to uphold a culture that rep- resents the company’s original core ethics and values and encourages staff to support charitable causes through company-wide and independent initiatives. The business has helped the Uncommon Friends Foundation, Muscular Dystrophy Association, American Cancer Society, Susan G. Komen, Junior Achievement of Southwest Florida, Shelter for Abused Women & Children, Habitat for Humanity of Collier County and more.

Wynn has been married to his high school sweetheart, Paula, for 26 years, and has two daughters, Sydney and Olivia. His favorite hobby is fishing. 

Small Business: Jennifer Wallace

Hotel General Manager, DoubleTree Suites by Hilton Naples

For DoubleTree Suites by Hilton Naples’s most recent Boss Appreciation Day, team members reflected on their most impactful experience with General Manager Jennifer Wallace.

One employee recalled when Wallace rolled up her sleeves during a busy morning at their in-house restaurant and began washing dishes; another talked about a time a pipe burst when the hotel was at full capacity and Wallace mopped up the water—shoes and pant legs soaked from the spillage—in the middle of the night, until it was under control.

“Her biggest act of kindness toward me was all her help during my mom’s last days. She gave me time to go to my homeland two times during a busy season, cared for me during the worst time of my life,” says DoubleTree employee Desiree Dayhoff. “She even brought delicious Spanish food and wine for me and my family during the memorial time. These are things I will never forget.”

The stories serve as a testament to Wallace’s dedication to the team, whether it’s helping them in their daily work or being there when they need it most. She’s routinely spotted around the hotel conversing with various department workers, to stay sharp on their needs and remain an accountable leader.

Wallace empowers her team to improve the hotel’s culture and guest experience so it can reach an annual goal as the top-ranking DoubleTree by Hilton. She holds brainstorming sessions and staff meetings to ensure ideas are heard and fairly acted upon.

Wallace leads the hotel’s community outreach program, which has benefitted Keep Collier Beautiful, St. Matthew’s House, Harry Chapin Food Bank and more. She’s a dedicated wife and loves music and cats.

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