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Inspiring Conversations with Melyssa Jaskiewicz of Leveling the Fields

Today we’d like to introduce you to Melyssa Jaskiewicz

Hi Melyssa, can you start by introducing yourself? We’d love to learn more about how you got to where you are today?
My journey to founding Leveling the Fields has been shaped by a mix of personal passion, professional experience, and a deep-rooted entrepreneurial spirit.
I currently serve as the Vice President of Sales at Sideline Sports, a family owned and operated business started by my sister and my father. I’ve had the privilege of driving innovative, gamification-focused engagement strategies in the sports world. It’s a role that has sharpened my ability to connect people through technology and storytelling, key skills that I’ve carried into this new venture.
Before my time in tech and sports, I earned my degree in e-commerce from Johnson & Wales University. I’ve always been captivated by technology’s power to create opportunities, and that fascination began early on. Growing up in a family of entrepreneurs, I saw firsthand the drive and creativity it takes to build something from the ground up. My dad and granddad both ran their own businesses, and watching them taught me the value of hard work, resilience, and leadership.
Throughout my career, I’ve balanced these influences: a love for innovation, a respect for entrepreneurship, and a passion for fostering connection and growth. Founding Leveling the Fields felt like the natural culmination of these elements. As a former athlete and someone who’s seen the transformative impact of sports, I recognized the barriers many young girls face when it comes to participation—whether those challenges are access, affordability, or opportunities to develop leadership skills.
Every step of my journey has shaped me into who I am, from growing up in an entrepreneurial household to my education and professional roles. I’m excited to continue growing Leveling the Fields and expanding opportunities for the next generation of young leaders.

Can you talk to us a bit about the challenges and lessons you’ve learned along the way. Looking back would you say it’s been easy or smooth in retrospect?
Of course, the road hasn’t always been smooth. Starting as a child, I struggled with both ADD and dyslexia, which often led to low confidence and self-doubt. It took time to learn how to overcome these challenges. One of the most important breakthroughs for me was learning to create systems to stay organized and focused—mostly through the use of technology. These tools became essential in helping me keep track of tasks and maintain productivity. However, technology alone wasn’t enough; I had to cultivate a strong sense of discipline to follow through on these systems consistently. Over time, this discipline became a cornerstone of my personal and professional success.
Another significant challenge has been finding balance as a working mom. Like many women, I’ve faced the ongoing struggle of managing priorities between work and family life. There are always demands pulling you in different directions, and it’s easy to feel stretched thin. For me, setting clear boundaries and being intentional about where I invest my time and energy has been key. I’ve learned to prioritize what truly matters and to give myself grace when things don’t go perfectly.

Thanks for sharing that. So, maybe next you can tell us a bit more about your business?
At Leveling the Fields, we specialize in breaking down barriers to sports participation for young girls. What sets us apart is our focus on holistic empowerment—we don’t just teach sports, we provide leadership training, personal development, and tools for long-term success. Our programs aim to instill confidence and resilience in every participant.
I’m particularly proud of the way we’ve built this organization from the ground up, with a strong foundation in community collaboration and support. Starting a nonprofit as someone with a background in sales and marketing has been a unique advantage. Many nonprofit founders come from service or educational backgrounds, but my experience in business strategy and relationship-building has helped move forward. I’ve been able to use my skills to establish key partnerships and design programs that truly meet the needs of the communities we serve.
Our main program, EmpowerPlay, offers girls from 3-5th grade an after-school multi-sport program designed to foster both athletic and leadership development. We want your readers to know that Leveling the Fields is committed to creating real, lasting change. We’re not just a sports program—we’re a movement to empower the next generation of confident, capable young leaders. Whether through volunteering, partnerships, or participation, there are many ways to support our mission and help us continue expanding opportunities for girls in need.

Is there anyone you’d like to thank or give credit to?
None of this would have been possible without the incredible people who have supported me and the mission from the very beginning. Kristan Shimpi has been by my side since day one. Her dedication and extensive background in nonprofit work have been pivotal to our success. Kristan has kept me on track and helped navigate the challenges that come with building a nonprofit from the ground up. I also owe a great deal of gratitude to our board members, Paige Yeater and Amanda Davis. They believed in the mission from the very start and have provided a solid foundation of support and guidance. Their commitment and encouragement have helped Leveling the Fields grow and thrive. I’m incredibly fortunate to have such a dedicated team of advocates and partners in this journey.

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