Retiring Waypoint CEO looks back on impactful career in nonprofit work

CEDAR RAPIDS — When Jaye Kennedy became the CEO of Waypoint Services in 2013, it felt like she was taking on the job that she’d been building toward her entire professional career.

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“One of the services that we officer is domestic violence services, and I lost my sister to domestic violence, so there was that real connection,” Kennedy said. “I just was so pulled to be here, and I guess I felt like she was encouraging me.”

Twelve years later, Kennedy is passing the torch. She will be retiring at the end of this year, and has already begun the process of shifting responsibilities to her replacement, Autumn Paine.

“It’s weird. It’s a bit emotional for me, slowly giving up and having her take the reins over on different things, which is exactly how it should happen,” Kennedy said. “I’m excited for Waypoint, I’m excited for Autumn, and I’m excited for me. I’m really excited for me.”

‘I saw our community through a totally different lens’

Kennedy didn’t set out to work in the nonprofit space. In fact, when she graduated with a business degree from Mount Mercy University in 1982, she didn’t have a plan for her future.

She ended up getting a job through a family friend as a broker for SCI Financial Group. There, she worked her way up to investment portfolio manager, a job that had her reaching out to the owners of investment accounts — sometimes by taking a small plane to visit them, as they were scattered throughout Iowa and the surrounding states — to keep them updated on what was happening with their investment.

“That really started me. A lot of what I do today is part of that. Yes, it’s understanding the economics side of investments, but really it’s being able to communicate and really build relationships with individuals and families and groups,” Kennedy said.

Through SCI Investments, Kennedy got involved in a “loaned executive” program for the United Way of East Central Iowa. Her company essentially lent her out to the nonprofit for a three-month period, which she spent visiting businesses and community groups to talk to them about how they could support the nonprofit.

“I didn’t know what United Way was, I’m embarrassed to say, but I was encouraged through work to get involved,” Kennedy said. “That changed my life. I saw our community through a totally different lens.”

Soon after Kennedy’s experience as a loaned executive, a position opened up for director of development with United Way, and she jumped at the opportunity.

“It’s hard to put into words how much I just loved the world of nonprofit fundraising,” Kennedy said. “I can’t tell you how much it just got into my soul. I loved it, and I loved the cause and being able to help people, and to match people that have the resources with people that need the help.”

A varied career in nonprofit fundraising

Kennedy spent the next 10 years at United Way. While there, she noticed that a lot of the smaller organizations she worked with needed help in certain aspects of the business and economics side of running a nonprofit, like creating fundraising plans, setting up endowment programs, or developing their boards of directors.

An idea started to form, but Kennedy felt she didn’t yet have all the necessary qualifications to provide the assistance she wanted to, having only been part of the funding side of nonprofit work. So, she left United Way, taking a position as director of development at Tanager Place.

“United Way is like an umbrella organization that raises money for agencies. I didn't have that firsthand agency experience,” Kennedy said.

After four years at Tanager, Kennedy felt ready to move into her next step: economic consulting for nonprofit agencies. She opened her own business, Kennedy Consulting, and worked with agencies across Iowa to develop and improve their economic processes.

Kennedy ran the business by herself, with a little help from her mother stuffing envelopes and assisting with administrative tasks. A couple of years later when she got a call from the University of Iowa offering her a job in academic fundraising — something she had always been interested in learning more about — she closed the business.

She spent several years working with University of Iowa alumni to bring more funds in for the school through alumni gifts.

“It was always great because, I mean, they knew why I was there, of course, to help them to create a gift in a way that they wanted it to be, like a scholarship, or that kind of thing,” Kennedy said. “It was really, really fun, but I missed working at an agency, working for more of a cause, a human service cause.”

Then in 2013, the CEO position opened up at Waypoint, and Kennedy said it felt like a perfect fit.

A family connection

When Kennedy was in high school, her older sister was married and living out of state. Her sister’s husband, who she had married after divorcing the father of her two sons, was financially stable enough to put her kids through private school.

He was also abusive.

“She loved her kids very much, and wanted to make sure that they got through high school in the school system they were in,” Kennedy said of her sister. “My parents and I didn’t know any of this was going on. My parents were called from out of state to come to the hospital because she had been severely beaten, and when they got there, they didn’t recognize her.”

Eventually, after the boys had graduated school and were living on their own, Kennedy’s sister got a divorce, but not before becoming dependent on alcohol to cope with the violence in her home. Self-medicating is common in these types of situations, Kennedy said, and her sister later died from liver failure as a result of alcohol use.

When Kennedy saw the job position open at Waypoint, she said it felt like the perfect opportunity to use her career experience to work to honor her sister’s struggle.

“It’s just so important that we have programs like the one at Waypoint,” Kennedy said. “We save lives. I know we do, and there's nothing more important than that.”

Choosing to retire

When Kennedy announced she was planning to retire, Waypoint’s board hosted a search for a new CEO, but Kennedy suspected from the outset that the role would be filled by Autumn Paine. Paine currently works as Waypoint’s chief development and marketing officer, having started the role one month before Kennedy was hired as CEO in 2013.

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“We've worked pretty much hand-in-hand all these years, and we’re very like-minded. She's very innovative, extremely creative, and very good with relationship building,” Kennedy said. “We always talk about, Waypoint is like a ship, and as the captain of the ship, you’re at the front of the ship, looking out for icebergs and islands. Miss the icebergs and go to the islands if they look like they would benefit you, and just always be looking out ahead of where we're going. She's very good at that. She's just excellent.”

Still, even knowing that Waypoint will be in good hands when she’s gone, Kennedy said the decision to retire was not an easy one. She likes to stay busy, and although she knows she’ll have plenty to do in retirement — between spending time with her husband, visiting kids and grandkids, pursuing her artistic hobbies like silk scarf painting, and even continuing to work part-time as a life coach — she’s anxious about the change.

“Retiring is extremely emotional for me,” Kennedy said. “My career has meant so much to me. It's been very dear to my heart. In my own way, I've been able to make a positive impact on the community.”

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