Alenka Winslett Celebrates 25 Years at College Now!
When it comes to nonprofit work, an organization’s functionality is like a song—the melody may lead, but the rhythm is what keeps everything in harmony. This fact rings true for our work at College Now, where the steady heartbeat of our work has been guided for the past 25 years by Alenka Winslett, our chief operating officer. Alenka’s career at College Now (then the Cleveland Scholarship Programs) began on January 2, 2001—and she hasn’t looked back since. As a first-generation college graduate and the daughter of Slovenian immigrants, Alenka has always carried the mission of College Now close to her heart. Reflecting on her time at Notre Dame Cathedral Latin (formerly Notre Dame Academy), Alenka often wishes College Now had been part of her high school experience — a thought that continues to inspire the purpose and passion she brings to her work every day.
While she didn’t have the guidance of College Now at her high school, Alenka always knew the path she wanted to follow. As a teenager, she was drawn to accounting and operations spending her summers working for her father’s tool and die company. There, she managed the accounts payable and accounts receivable logs, processed the invoices and handled the incoming checks— prepping deposit slips and balancing the books. Tasks that might have felt tedious to others captivated Alenka — she found the work fascinating and engaging from the very start.
Alenka continued her education at the University of Cincinnati, where she majored in accounting. “It was the furthest place from Cleveland where I could still get in-state tuition,” she says tongue-in-cheek. Speaking more seriously, Alenka reflects on her parents’ insistence on the importance of higher education. “It wasn’t a question of ‘if’ I was going to college— it was a question of ‘where’,” she says. Alenka credits her alma mater’s renowned business school for shaping the foundation that would later fuel success in operations and leadership.
When asked about her proudest achievement, Alenka points to the role she’s played in the organization’s growth during her tenure. While she began her tenure at College Now as chief financial officer and has long served as chief operating officer, Alenka has also stepped in as interim chief executive officer and chief programs officer when needed—serving as a steady hand when the organization was in medias res. She credits much of her confidence and resilience to the late Pat Mullin, former board chair and mentor, who reminded Alenka of her ability to lead with purpose during times of transition.
Outside of her role at College Now, Alenka is quite active in the community. Serving as a College Now mentor, treasurer of the board for a Slovenian social club and vice chair of the board for the Slovene Home for the Aged, Alenka rarely sits still. This holds true in her personal life as well— being an avid traveler, often planning her next trip while still on the current one. When life occasionally slows down, Alenka loves word puzzles. Just as she thrives on problem-solving at College Now, Alenka has a knack for tackling puzzles wherever she goes— it’s the kind of curiosity she just can’t turn off.
Reflecting on the last 25 years at College Now, Alenka notes that while there have been countless changes, it still feels just as much like a family as it did when she walked through the doors on that chilly January morning in 2001. She looks forward to every day at College Now knowing no two are alike—always ready for the next song to carry the rhythm forward.