Pushing Boundaries for the Greater Good: Ray Ackerlund, (’97)
By Kim Westerman | February 2025
Ray Ackerlund is a quiet disruptor. An introvert by nature, Ackerlund’s first job out of college was in sales, a field that seemed like a foreign language to him. He now runs the company that offered him his first opportunity to think outside the box, starting with his stereotypes of what salespeople do. Hint: It’s not about sly persuasion or stringing together sound bites; it’s about thinking critically and helping people solve problems.
His time at UWSP was transformative. Although he traveled during his four years in the Air Force before starting college, he had grown up in Colfax, a town of 1,000, on a dairy farm. Living in England for three-and-a-half years after basic training was, in many ways, the beginning of a life of service. But it all came together for him at Point. He met his wife, Connie, at the school bookstore where they both worked, and two professors, in particular, helped shape his adult life.
Business professor Jim Haine brought real-world challenges into the classroom in the form of case studies and pushed students to think creatively about alternative perspectives on common problems in the field. Communications Advisor and magnetic public speaker C.Y. Allen connected with students and motivated them to identify their strengths, inspiring confidence to run with them.
Twenty years into his career at Skyward, an educational software company that offers school districts an online hub for managing operations, payroll and other essential functions, Ackerlund finds himself embracing the notion of service beyond his day job. He’s also the vice president of the UWSP Foundation Board, where he works behind the scenes to help provide scholarships and program support for the UWSP campus. His company is also the benefactor of the Skyward Scholars Program, which provides scholarships for UWSP students and internship opportunities at the company. UWSP recognized the generosity of this gift by naming the multi-activity center in Champions Hall the “Skyward Fieldhouse.” He spends his time thinking about ways to drive meaningful change. His best advice? “Get comfortable with discomfort. This will help you see challenges from new angles and reach creative solutions.”
Ackerlund is also chair of the Business Advisory Council for the Sentry School of Business and Economics, and it’s no surprise that he has many UWSP alumni on his staff. What kinds of employees does he look for? First and foremost, he wants people who aren’t afraid to be vulnerable, who are strong critical thinkers, and who are willing to put in time learning the ropes before advancing to greater responsibility.
His advice for the changemakers of the future? Don’t be afraid to make discoveries about who you are and what you can do — be open to opportunities outside your wheelhouse. And most importantly, be willing to push your own boundaries in the service of personal and professional growth. He considers today’s essential skills to be critical thinking, communication skills (both written and verbal), perseverance through adversity, and adaptability in a constantly changing world.
At this point, retirement is on Ackerlund’s mind. He and Connie have seen their two kids through to young adulthood, and now he is thinking about what’s next. One thing he knows for sure: Passion can move the world, and Pointers lead with it.
