Episode 13: Featuring Calli Bakken, Founder of Wiggle Work & Interim Executive Director, Matthew's Voice Project
Here’s a question worth sitting with: how much has your organization spent on HR technology in the last three years, and how much has actually changed?
Calli Bakken has spent 15 years watching companies answer that question with more tools, and seeing what happens when the data is there but the leadership will isn’t. That realization, combined with a personal experience navigating a medical crisis as a new parent in 2020, led her to found Wiggle Work: a consulting company helping mid-size employers build childcare that actually works. In this episode, host Kim Bohr, President and COO of SparkEffect, explores with Calli what it takes to stop patching the system and start building something better.
Listen
Watch
What You’ll Discover
- Why data alone doesn’t change culture – and what Calli learned after years of watching companies collect it without acting on it
- The Mayo Clinic story – what calling every morning for three and a half weeks taught her about what parents actually carry into work
- How traditional corporate childcare models break down financially – and why opening seats to the community makes them viable
- What it takes to lead a nonprofit in constant crisis – where the mission itself shifts based on what the community needs that week
- Why Calli is targeting mid-size companies in non-metro communities first – and what makes them more ready for this than the big names
- What childcare access does for employee trust – that a benefits package simply can’t replicate
- What she’d say to anyone stuck in a workplace that keeps moving the goalposts
Episode Highlights
[00:01] Introduction: Technology Can’t Fix What Leadership Won’t Acknowledge
[01:06] Trust Is Forged in the Hard Moments: Calli’s Lens on Leadership
[02:16] Matthew’s Voice Project: What Leading in Constant Crisis Actually Looks Like
[10:12] No Magic Position: Why Calli Decided to Build Something Herself
[12:54] What Drew Her to HR Tech, and What Eventually Broke the Spell
[18:26] Inside a Startup Culture Where the Goalposts Keep Moving
[27:37] Early 2020, a New Baby, and a System That Wasn’t Built for Real Families
[30:45] The Wiggle Work Model: Childcare as a Community and Workforce Strategy
[41:53] For Anyone Who’s Stuck: Don’t Get Paralyzed. Take the Next Small Step.
Key Takeaways for HR Leaders
- Technology doesn’t fix a leadership will problem. Calli spent years watching companies implement tools to address culture challenges they weren’t actually willing to confront. The data was there. The conclusions were clear. But acting on them required a kind of organizational honesty most weren’t ready for. If your people programs aren’t moving the needle, it may be time to look past the tools.
- What employees want is simpler than we’ve made it. They want to feel confident in their work when they’re at work, and then go home. Most organizations design for the small percentage of employees who are work-obsessed, and build culture strategy around them. The majority are working to fund a life. When you forget that, you lose them.
- Childcare is a retention and trust problem, not a benefits problem. When an employer makes childcare accessible, it doesn’t just reduce stress. It signals that the organization sees employees as full human beings, not just job functions. That trust signal is hard to manufacture any other way. And with return-to-office mandates accelerating, the organizations that solve this first will have a real retention edge.
- Community-integrated childcare is more financially viable than employee-only models. The traditional corporate childcare model breaks down because enrollment fluctuates and infant care is expensive to staff. Calli’s model opens remaining seats to the broader community, which keeps ratios full, sustains the operation, and turns the employer into a community anchor.
- Mid-size companies in non-metro markets are more ready for this than you’d expect. Large, well-funded companies have dabbled in corporate childcare for reputational reasons. Calli is focused on smaller organizations in communities that are actively losing people to cities. The urgency is real, the red tape is lighter, and the appetite for practical solutions is high.
About Our Guest
Calli Adamson Bakken is a founder doing work that sits squarely where people strategy, behavioral data, and real organizational change meet. After 15 years in HR, HR tech, and early-stage startups, she left traditional employment to build Wiggle Work, a company mobilizing workplace childcare as a strategic answer to one of today’s most urgent workforce problems.
That move was shaped in part by her work as Interim Executive Director of Matthew’s Voice Project, a nonprofit supporting students experiencing homelessness. The role has deepened her commitment to building systems that work for real families, not just job descriptions.
Calli is also the co-host of the Work Sucks podcast and a serial DisruptHR organizer, known for pushing honest conversations about what work should actually look like when people come first
Connect with Calli Bakken
LinkedIn: Callie Adamson Bakken
Notable Quotes
Calli Bakken:
“No amount of tech is going to convince employees of those things. What’s going to convince employees is how you show up and support them and make their day-to-day experience more enjoyable, more tolerable, more functional.”
“It doesn’t matter how great the tech is. If it adds burden to the employee’s experience and the work that they need to do, they’re not going to use it.”
Kim Bohr:
“Technology can’t fix what leadership won’t acknowledge.”
“Childcare and elder care are two of the top disruptions in the personal column. And that doesn’t even account for what happens in the professional column. And yet the two are constantly overlapping.”
Related Resources
- SparkEffect Trust Study – Research showing that 71% of organizations faced disruption in the last 24 months, but only 36% emerged stronger (https://info.sparkeffect.com/trust-study-2025-download)
About Courage to Advance
Courage to Advance explores how visionary leaders are building the organizations they wish existed, companies that prove business doesn’t have to be dehumanizing. Hosted by Kim Bohr, President and COO of SparkEffect, each episode features executives who refuse to accept that traditional corporate practices are inevitable, sharing the experiments, resistance, and breakthrough results of choosing human flourishing alongside business success.
Subscribe anywhere you listen to podcasts. You can find links to all platforms HERE!
Visit: couragetoadvancepodcast.com for free resources and tools.
Receive New Podcast Episodes in Your Inbox