Meet the candidates vying for Winter Springs City Manager

Winter Springs begins a crucial job search this week, interviewing five candidates looking to become city manager.

In late February, Shawn Boyle suddenly retired as city manager, citing, in part, emotional and physical distress from the job. “The emotional and physical distress that I have been under make me unable to continue working as the city manager for the City of Winter Springs,” Boyle’s statement read. 

Winter Springs Mayor Kevin McCann said he’s looked at the bios of the candidates and is optimistic. The first interview with candidates was on Tuesday, and the final round of interviews will be done on Saturday. 

When asked about the timeline to get the city manager hired?

“The sooner the better,” McCann said. “This is the most important decision this commission will make. We’ve got some great candidates.”

One candidate who’s not in the running? Interim City Manager Phil Hursh, who was previously the public works director. Hursh declined an interview request about the process of hiring a city manager, since the city has hired a consultant, Korn Ferry, to run the process. 

“Korn Ferry will collect applications, and the top five candidates will be presented to the Mayor and Commissioners,” Winter Springs Spokesperson Matthew Reeser said. “The vote for the next City Manager will need to be a super-majority decision with at least four being in favor.“ 

Oviedo Community News reached out to all five candidates for the position and asked them the same questions. Four of them responded. See below for a quick synopsis of the candidates and their responses to the questions. The candidates are listed in alphabetical order.  

Candidate: Dale “Doc” Dougherty

Current position: City Manager of Garden City, Michigan

Consultant’s assessment: Mr. Dougherty spent approximately 15 years in Florida municipal management working for various sized communities in community affairs and parks and recreation. In addition to Florida, Doc brings municipal experience from Georgia, South Carolina, and currently Michigan. He believes that city management is not a job but a lifestyle. He has implemented staff orientation and integration programs including the T.E.A. Program which creates a personnel structure based on Trust, Empowerment, and Accountability.

Candidate: Christopher T. Edwards

Current position: Economic Development Director, City of New Smyrna Beach

Consultant’s assessment: Mr. Edwards has an extensive background in municipal economic development including at the City of Tallahassee and the City of New Smyrna Beach. He has been involved in capital improvement projects, master plans, and redevelopment initiatives. He prides himself on being innovative and results-oriented with extensive experience in operations, strategic planning, and project management. He has served in economic development, community redevelopment, and public infrastructure while in public service.

Candidate: Kathryn M. Matos

Current position: Assistant City Manager, City of Boynton Beach, Florida

Consultant’s assessment: Ms. Matos has several years of municipal project management experience in various departments and at different levels of government. She has overseen legislative affairs, personnel, environmental conservation, budget, and operations as well as implementing several technology/software updates creating a more customer-focused process for the community. She views the role of city management as an apolitical position that shares expertise and implements the direction set by the commission.

Candidate: Jonathan McKinney

Current position: Assistant City Manager, City of Port Orange, Florida

Consultant’s assessment: Mr. McKinney has extensive municipal finance expertise in large and small Florida communities. He has implemented comprehensive financial policies and procedures that align with best practices. He has led communities through audits and multiple state accreditation programs. Outside of finance, he prides himself on being able to build cohesive, expert staff across different departments.

Candidate: Christopher R. Miller

Current position: County Administrator, King George County, Virginia

Consultant’s assessment: Mr. Miller brings decades of municipal management experience and has completed several impressive infrastructure projects across multiple states with varying levels of government. He currently serves as the County Administrator for King George County in Virginia where he oversees hundreds of employees and a $115 million budget. In his career he has held multiple government and quasi-government positions in Colorado, Alabama, Texas, and Virginia.

Oviedo Community News asked all five candidates for the top job the same question. Four of them returned responses. Christopher T. Edwards declined an interview while he is in the hiring process. The answers below have been edited for clarity. 

What drew you to the City of Winter Springs as a candidate for city manager?

Dale “Doc” Dougherty: I love the energy of local governments in Florida. I spent half my career (15 years) working in two communities in Florida (a town in Palm Beach County & Hillsborough County). I only left the state to obtain my MBA from Notre Dame and to become a city manager in Michigan. Both reasons were to better develop my skill set. Moving to Winter Springs would be like coming home … AGAIN!

It was always our plan to move back to the Sunshine State after making positive changes in Michigan. In addition, our eldest daughter just finished college at UF and moved to Melbourne last year to start her career as a software engineer.

I also listened to several Winter Springs meetings, which I felt were professionally run. It additionally appeared that the staff was well prepared. Having a dedicated staff and a generally unified City Commission is very attractive to me.

Kathryn M. Matos: Winter Springs is a city on the rise; a destination city for people in all stages of life. The opportunity to serve Winter Springs as city manager is the pinnacle of my career. I have spent 11 years in municipal management, and I am passionate about building resilient communities and making local government accessible, responsive and efficient. I am all about constant improvement and building the brand of the city through transparent communication and excellence in customer service.

Additionally, my sister and her family live in unincorporated Winter Springs and many of my extended family members live in the greater Orlando area. I have spent quite a bit of time in Winter Springs, visiting many of its parks and amenities over the years. A couple of weeks ago, I was in town and visited Trotwood Park – there was a birthday party in the pavilion, the playground was full of children and families. The sense of community was tangible. It was a small but surreal moment where my husband and I both looked at each other and got excited about moving to Winter Springs. 

Jonathan McKinney: Two things. First, is the opportunity to expand on the existing strengths of this community and help to make it a better place to live.  I am inspired by the opportunity to make a difference in the lives of the people who live and work in Winter Springs.  Second, is the location as it is within Central Florida and my family and I want to remain in close proximity to the beaches. 

Christopher R. Miller:  I have had the privilege of serving in a number of municipal, county and regional jurisdictions throughout my career, including my current position with King George County, Virginia. I am looking forward to learning more about all the wonderful attributes that Winter Springs has to offer.  

My interest in this position is based on a variety of reasons. One, its location is ideal. Second, I started my career serving in municipal governments and this opportunity in Winter Springs would allow me to return to that area of concentration. Third, I feel my background and experience match up well with what the elected and appointed leadership in Winter Springs are looking for in the next city manager.

2) Understanding that things may change if you’re in the position, but what do you see as the biggest challenges for Winter Springs?

Dale “Doc” Dougherty: Change in leadership – Whenever there is a change in leadership, employees of a community tend to hunker down and wait until they get a good feel for the personality of the new city manager and their expectations. This is always a challenge for a new manager.

Population Growth – After experiencing uncontrolled growth in Hillsborough County (Tampa), I have become a firm believer that the infrastructure of the community must keep pace with its growth. Uncontrolled growth leads to traffic nightmares, which can easily destroy a community’s quality of life.

Wastewater Treatment Facilities – The refurbishment and the replacement of the two wastewater treatment facilities, and the associated infrastructure, as well as the potential long-term costs of the facilities, is an issue that will be front and center for years.

Audits – Correct any issues and implement any appropriate policies that would relate to legitimate findings from the recent external audits.

Kathryn M. Matos: In light of the experience during Hurricane Ian in 2022 that put a magnifying glass on infrastructure and flooding issues, it is vitally important that we make the city resilient to handle future flooding events. Ground water level and quality of water is essential. Even with understanding that presently water quality is still in good ranges, we cannot discount resident’s concerns to plan ahead and ensure water quality for the future. It is important to be proactive, not reactionary and to work closely with the scientific community to monitor wells and allay residents’ fears about flooding and address their concerns. Across the state, cities are experiencing less capacity in existing infrastructure so the key will be increasing infrastructure capacity. The dual benefit of this is also the ability to improve the city’s rating for the Community Rating System (CRS) and reduce flood insurance rates, which will drive down costs for homeowners.  

It is also vitally important to ensure the city is in compliance with any county, state or federal regulations and to ensure that any recent reports from any entity are addressed immediately. 

Jonathan McKinney: I believe there are two immediate challenges for the next City Manager.

1. The Water, Wastewater and Reclaimed Utility System infrastructure improvements and how to fund these projects.  This could be accomplished through utility rate designs, state appropriations and grants.
2. Among my strengths are the management and finances of municipal operations, therefore, I believe I am well situated to guide the city with the necessary corrective actions of the preliminary findings resulting from the auditor general’s operational audit.

Christopher R. Miller: As with other similar-sized communities in Florida and other parts of the country, I am certain the leadership of Winter Springs faces the constant challenge of trying to maximize available financial and human resources and its physical infrastructure to meet the ever-increasing needs of its citizens for higher levels of service delivery.  Additionally, the leaders of the community face the great challenge of governing and preserving democratic ideals within an atmosphere of high demand for transparency and instantaneous communication and engagement about policy and service delivery.  I believe my background and experience has me well-suited to be of assistance to the City of Winter Springs in managing these challenges and I look forward to further discussion with the leadership of the community regarding their insight into such issues and other areas of service.

3) What do you see as the biggest opportunities in Winter Springs?

Dale “Doc” Dougherty: Financially Stable – With the recent increase in the city’s credit rating, it appears that the city is financially stable. This will assist in focusing on infrastructure, crime reduction, community programming and miscellaneous capital projects and purchases.

Controlled Growth – Due to Winter Springs being a kept secret over the years, unlike other areas in Central Florida, the city has the ability to grow strategically.

Quality of Life Issues – I understand the city established a parks improvement plan and has experienced expanded community events. These issues lead to a great quality of life.

Hiring an outsider – I am obviously biased in this regard, but I had great success coming into a community with no friendships or debts owed to the past. I am able to quickly find deficiencies that insiders may overlook. I also have the ability to bring best practices which I have used or experienced from around the country.

Kathryn M. Matos: I think there are so many amazing things already happening in Winter Springs, from the quality of the city’s parks to the overall desirability to live in Winter Springs. An opportunity I see is to continue telling the amazing stories of what is already happening in the city. The current trend of focusing on the negative makes it easy to miss the positive. I have been keeping tabs on the city’s social media pages and newsletter and I love the content the team is already putting out – I would love to see more resources dedicated to communication and transparency so that residents can be made aware of what their city and their staff is doing every day to continue making their home the best place to live. 

In listening to Commission meetings, a lot of the concerns I hear from residents surround infrastructure investment and development. Ensuring that the finances of the city are setup to ensure the long term resilience of the city from an infrastructure perspective is one of my top priorities. 

In terms of economic development, I would focus energy on the city’s homegrown businesses. In my personal experience through visiting Winter Springs, when a new local restaurant opens, the doors are packed because the residents want to support local eateries. As a city, what are the things we can do to ensure the long-term viability of these kinds of businesses? Has a market survey been completed recently to see what residents and business owners are looking for? Community input is crucial. 

Another priority is maximizing the use of technology to increase efficiency and make services more seamless for residents. I am very happy to see that the city’s permitting process is online and I would work with the staff to continue to improve efficiencies that could be realized in other services across the city to make them more seamless and accessible for residents.  

Jonathan McKinney: Our people: the citizens, business owners and employees of Winter Springs.  We want to dream big and move forward to overcome the challenges that face everyone in Winter Springs while maintaining the quality of life that has kept Winter Springs the best-kept secret in Central Florida.

Christopher R. Miller: From my knowledge of the community, I would consider the city’s terrific leadership (both at the elected, appointed and staff levels) as one of its greatest opportunities for service delivery and policy making in the future. Additionally,  Winter Springs, citizens and community leadership are significant assets and provide even further opportunity for the community’s future.  Finally, I would consider the location of the community as a great opportunity for the community. 

However, I look forward to hearing from the mayor and city commission on their perspective of the community’s opportunities.

4) It’s no secret that there has been turnover and some turmoil in the city. What message would you have for city staff?

Dale “Doc” Dougherty: Unfortunately, all communities experience periodic bouts of turmoil.

What I have done in my last few positions is, after my first month of employment, I bring all the employees into an auditorium to communicate my vision. Through a one-hour PowerPoint presentation, I outline my history and then describe my initial impression of the organization. After explaining the importance of being responsive and looking at the organization from an outsider’s perspective, I later detail what I expect from the staff and what the staff can expect from me. If one department can assist another department in accomplishing its goals, they are expected to do whatever they can. I see mutual respect as professionals to be a positive way to develop working relationships and an effective team. There is no doubt that this orientation meeting sets the tone for how the organization is going to change positively, and how I understand the importance of everyone’s contribution to the success of the community.

I then unveil the Ethical Foundation I live by and encourage my staff to adopt: “Be Fair; Be Honest; Tell the Truth; Keep Your Word; Exercise Integrity.” Signs are posted in every government building. I expect the staff to be excellent and innovative in their actions, but they must always stay within the framework of the ethical foundation in everything they do.

I always try to be the manager that I wish I had. Therefore, for the employees who want to see Winter Springs succeed, I will give them the trust, support, and resources to be successful in their area of expertise.

Kathryn M. Matos: My biggest message to staff is keep moving forward. My goal is to create stability on the team. I would take a look at where employees’ skill sets best serve the team. I see myself as a liaison between the Commission and the staff and it is my job to ensure that everyone is rolling in the same direction. I care deeply about staff’s ability to progress professionally and to be able to take care of their families and home lives so that they can perform their best on the job. Public service is a beautiful calling and local government in particular is a fulfilling career that allows you to have a direct impact on your community on a daily basis. I would work to create a fun, comfortable work environment where people enjoy coming to work and staff can continue to do great things for the City. 

Jonathan McKinney: This has brought opportunity, to build a team by hiring the best individuals for positions, establishing trust through open communication, transparency, and stability that will serve the citizens of Winter Springs in a manner that brings out the best of this great community.

Christopher R. Miller: I would only offer the following in response to your question: If I were selected as Winter Springs next City Manager, I look forward to serving both the mayor and Commission and city staff and to learning from them and assisting them in their continued service to the community.  I am confident I could provide steady, seasoned, innovative, highly facilitative and consensus-oriented management and leadership service to the community.