The RSPA W2W Leader of the Year award honors a trailblazing woman in retail technology annually at RetailNOW. The 2025 RSPA W2W Leader of the Year was awarded to Sandee Finley of reseller PaySafe Associates.
Sandee has spent 20 years in the retail IT channel and is known for her strategic leadership, industry expertise, and dedication to mentoring others. She began her career in customer service and rose through the ranks by driving growth, building high-performing teams, and leading complex integrations.
Outside of work, she mentors individuals and gives back through organizations including Houston’s Society of Royals and the LGBTQAI+ community. A dedicated RSPA member, she represents PaySafe Associates on the W2W Advisory Group, W2W Community, and VAR Business Growth & Development Community.
We asked Sandee about her journey and growth opportunities for women in today’s retail IT channel:
- What first drew you to a career in retail technology, and what continues to excite you about it?
I was drawn to retail technology because it sits at the intersection of people, innovation, and problem-solving. Early in my career, I discovered that technology in this space doesn’t just power transactions — it helps businesses grow, adapt, and better serve their customers. Behind every system or solution is a real business owner trying to build something meaningful, and that human element always resonated with me.
What continues to excite me is the constant evolution. The retail and payments landscape never stands still, which means there is always something new to learn and new challenges to solve. I’ve always been energized by environments where innovation is encouraged and where collaboration across the channel can create meaningful progress. Knowing that the work we do helps businesses succeed and communities thrive keeps me passionate about this industry every day.
- What meaningful changes have you seeninthe channel during your career, and how have they impacted your work?
During my career, I’ve seen the channel evolve from a more transactional environment into one that truly values collaboration and innovation. Technology has advanced rapidly, but what has stood out the most to me is the way partnerships across the channel have strengthened. Organizations and individuals are more willing to share ideas, experiences, and solutions in ways that help everyone move forward.
Another meaningful shift has been the growing recognition of diverse voices in leadership. The industry is stronger when different perspectives are welcomed and valued. For me, that evolution has reinforced the importance of building relationships, mentoring others, and helping create spaces where more voices can contribute to the future of the channel.
- What motivates you to embrace innovation and take on new challenges in your role?
Curiosity has always been a strong motivator for me. I believe that growth happens when we step outside of what feels comfortable and remain open to learning. Innovation often requires courage — because stepping into new territory means you may not have all the answers right away.
What motivates me most is the impact our work can have. When technology helps a business operate more efficiently, reach more customers, or grow in ways they never imagined, it creates ripple effects that extend far beyond the transaction itself. Being part of an industry that empowers entrepreneurs and businesses to succeed is incredibly rewarding and continues to inspire me to take on new challenges.
- Can you share a defining moment in your career that influenced your leadership path?
One of the most defining moments in my career came when I realized that having the title of a leader didn’t necessarily mean I fully understood what leadership truly required. Early on, I found myself reflecting deeply on whether I was showing up in a way that genuinely supported and inspired the people around me.
That realization was humbling, but it also became a turning point. I made a conscious decision to invest in myself — seeking mentorship, learning from others, and focusing on empathy, communication, and self-awareness. I came to understand that leadership isn’t about authority; it’s about responsibility. It’s about how you show up for people, how you listen, and how you help others grow. That moment reshaped my approach to leadership and continues to guide me today.
- What challenges have you encountered as a leader, and how have you overcome them?
One of the greatest challenges in leadership is balancing results with humanity. In fast-moving industries, there can be immense pressure to focus solely on outcomes, timelines, and performance metrics. But over time, I’ve learned that true success comes from remembering that behind every result are people.
Leading with empathy while maintaining accountability has been one of the most important lessons in my leadership journey. Empathy doesn’t mean lowering expectations — it means understanding your team, communicating openly, and creating an environment where people feel supported and valued. When people know they are respected and heard, they bring their best ideas, their creativity, and their dedication to the work. That kind of culture ultimately drives stronger results and stronger teams.
- How do you mentor and uplift other women in the industry?
Mentorship, to me, begins with encouragement and connection. Throughout my career, I’ve experienced firsthand how powerful it can be when someone believes in you and takes the time to support your growth. Sometimes a simple moment of encouragement can shift someone’s confidence and help them see possibilities they may not have seen for themselves.
I try to pay that forward by sharing knowledge, offering guidance, and creating space for open conversations. I want women in this industry to feel confident stepping into leadership roles and bringing their voices to the table. Mentorship isn’t always formal — it can be a conversation, a piece of advice, or simply reminding someone of their strengths when they need it most.
- How has your community involvement across the channel influenced your leadership style, and why do those spaces matter for the industry’s future?
Being involved in the broader community across the channel has deeply influenced my leadership perspective. It has shown me how much stronger our industry becomes when people collaborate, support one another, and share their experiences openly.
These communities create opportunities for mentorship, innovation, and connection. They allow leaders to learn from one another and ensure that knowledge and opportunities are passed along to the next generation. For the future of the industry, these spaces are essential because they foster inclusion, creativity, and progress.
- What impact do you hope to leave on the industry and future women leaders?
The impact I hope to leave is one of authenticity, encouragement, and opportunity. I want future women leaders to know that they don’t have to change who they are to succeed. Strength in leadership can come from empathy, resilience, integrity, and the courage to be authentic.
If my journey can help create more space for women to grow, lead, and bring their unique perspectives to this industry, then that’s a legacy I would be incredibly proud of. At the end of the day, leadership is about lifting others and helping build a future that is stronger and more inclusive than the one we inherited.
Leadership isn’t just about the impact you make today. It’s about the people you inspire, the opportunities you create, and the example you leave behind — for today, for tomorrow, for forever.
RSPA and its members continue to collaborate and create opportunities. A prime example is best practice sharing that takes place in the RSPA Community meetings. The RSPA W2W Community meets to provide a support network and resources for women as they enter and continue to advance in the retail technology industry. If you would like to get involved in the W2W Community, please email RSPA Member Services Team at Membership@GoRSPA.org.
The RSPA W2W Leader of the Year was created to recognize a woman in the Retail Technology Industry, who is determined to reshape the industry and create a smarter and more inclusive future. This honor recognizes a woman who has demonstrated key characteristics of a pioneer paving the way in the Retail Technology Industry.
