As Tiffany Winemiller reaches her first 100 days as Gateway Community Services’ President & CEO, she reflects on what she has learned, what inspires her, and where she sees Gateway heading next. From strengthening our services and supporting our team to expanding our impact across the community, Tiffany shares her perspective on leadership, the opportunities ahead, and her vision for Gateway’s next chapter.
Read the full conversation and hear directly from Tiffany about her first 100 days—and what comes next for Gateway.
Interviewer: What has surprised you the most and what have you learned that you didn’t know before?
Tiffany: Having been part of this organization for many years, including serving in an executive leadership role, I entered the CEO position with a strong understanding of our programs, operations, employees, and the behavioral health needs of our community.
What has surprised me most during my first 100 days is how different the organization looks from the CEO’s seat. I have gained a much deeper appreciation for the number of relationships and competing priorities that must be balanced every day—from employees and clients to our Board, funders, community partners, elected officials, and regulatory agencies. I have also learned how important it is for the CEO to remain focused on the long-term sustainability of the organization while still staying connected to the day-to-day realities of the people providing services.
One of my greatest takeaways has been that leadership at this level is less about having all the answers and more about listening, asking the right questions, communicating clearly, and empowering a strong leadership team. These first 100 days have reinforced for me that our greatest strength is our people and their commitment to serving individuals and families throughout Northeast Florida.
I have also developed an even greater appreciation for the complexity of behavioral healthcare funding and the importance of advocacy, partnerships, and diversification of revenue. The need for these services is continuing to grow, and ensuring that nonprofit providers have the resources and workforce necessary to meet that need will require strong collaboration across our community.
Interviewer: Have you learned anything from the staff?
Tiffany: Absolutely. One of the most important things I have learned is that the people closest to the work often have the best insight into what is working, what is not, and where we can improve.
Our staff have reminded me of the importance of listening and staying connected. They see firsthand the challenges our clients and families face, and they bring tremendous knowledge, compassion, and creativity to their work every day.
I have also learned that communication matters more than you sometimes realize. Employees want to understand not only what decisions are being made, but why they are being made and how those decisions connect to our mission and future.
Most importantly, our team has reinforced for me that leadership is not about one person. Gateway’s success comes from the collective commitment of people throughout the organization. My job as CEO is to listen to them, support them, remove barriers when I can, and make sure they know how important their work is to Gateway and to the community we serve.
Interviewer: What has been your biggest challenge?
Tiffany: My biggest challenge has been learning to step back from the operational role I held for many years and fully embrace the role of CEO. I spent much of my career being very close to the day-to-day operations of the organization, so learning when to stay involved and when to trust and empower my leadership team has been an adjustment.
I have also had to become comfortable with the fact that, as CEO, there will always be more needs than resources and more priorities than time. Behavioral health organizations operate in an increasingly complex environment, and difficult decisions are sometimes necessary to protect the long-term strength and sustainability of the organization.
There are so many things I am proud of at Gateway, but I am most proud of our people and their unwavering commitment to our mission. Behavioral healthcare is challenging work, and every day our employees show up for individuals and families during some of the most difficult moments of their lives. I am also incredibly proud of the breadth of services Gateway provides and our ability to meet people wherever they are in their recovery journey. We have continued to evolve as the needs of our community have changed, while never losing sight of why we are here—to help people build healthier, more productive lives.
I am proud of Gateway’s reputation and the trust we have built throughout Northeast Florida. Our relationships with community partners, funders, healthcare organizations, and local and state leaders have allowed us to expand our impact far beyond what we could accomplish alone.
Finally, I am proud of Gateway’s resilience. Like many nonprofit behavioral health organizations, we have faced funding challenges, workforce pressures, and an increasingly complex healthcare environment. Yet we continue to adapt, innovate, and find ways to serve our community.
After being part of Gateway for many years, becoming CEO has made me even more proud of what this organization represents. I feel a tremendous responsibility to honor what has been built here while making sure Gateway remains strong, relevant, and sustainable for the people who will need us for many years to come.
Interviewer: Have your priorities/visions of Gateway changed since day one? What advice would you give on day 1?
Tiffany: Over these first 100 days, I have become even more focused on long-term financial sustainability, strengthening our workforce, developing our leaders, building community partnerships, and making sure we are positioned to respond to the changing behavioral health needs of our community. I have also realized that we do not have to accomplish everything at once. Sustainable change takes time, and sometimes doing fewer things exceptionally well is more impactful than trying to address everything at the same time.
Interviewer: What do you think staff need from you the most moving forward?
Tiffany: I think our staff need me to be present, transparent, consistent, and willing to listen. They need to know where Gateway is going, what our priorities are, and how the work they do every day contributes to our success.
They also need honesty. I may not always have the answer they want to hear, and there may be times when difficult decisions have to be made, but I can commit to communicating openly about the “why” behind those decisions whenever I can.
I also believe staff need to feel heard and valued. Some of the best ideas for improving Gateway will come from the people doing the work every day, and I want to create an environment where employees feel comfortable sharing those ideas and know their voices matter.
Most importantly, I want our staff to know that I will advocate for them just as strongly as I advocate for the people we serve. If we take care of our employees, give them the tools and support they need, and create a culture where people feel valued and connected to our mission, we will be a stronger organization for our clients and our community.
Interviewer: What decisions/changes are you most confident about in these last 100 days?
Tiffany: I am most confident about the decisions that have strengthened our leadership team and positioned Gateway for long-term stability. One of my priorities has been making sure we have the right people in the right roles, empowering our leaders to make decisions, and creating greater accountability throughout the organization.
I also feel confident about the steps we have taken to be thoughtful and disciplined financially. Not every decision has been easy, but I have tried to make decisions based not only on what Gateway needs today, but on what will keep us strong and sustainable for the future.
I am particularly proud of our increased focus on communication and transparency. I want our employees to understand where we are going, the challenges we face, and the role they play in our success. I believe trust is built when people hear from leadership consistently—not just when things are going well.
I am also confident in our continued focus on strengthening community partnerships, advocating for behavioral health funding, and looking for opportunities to grow and diversify our resources.
I certainly don’t believe every decision I make will be perfect. What I am confident about is the process: listening to the right people, asking difficult questions, considering the impact on our employees and clients, and ultimately making the decision that I believe is best for Gateway and our mission.
