Chris Diller
Operations Leader
Minneapolis, MN
Expertise
Operational Strategy & Execution
Financial Oversight
Process Optimization
Agile & Product Leadership
Executive Coaching & Supervision
Certifications
ICF Associate Certified Coach
Scrum Alliance Certified Team Coach
ShiftPositive 360
Chris Diller is a versatile Operations Leader who excels at the intersection of technical strategy and human-centered leadership. With a background leading Agile and IT initiatives for major organizations like Target and Blue Cross Blue Shield, Chris brings a "tech wizard" approach to complex operational puzzles. He specializes in driving financial health and system efficiency for growing firms, combining rigorous analytical skills with deep emotional intelligence. As a trained executive coach, Chris is dedicated to building scalable systems that support healthy, high-performing organizational cultures.
Why I Work
“I am passionate about helping teams and leaders better understand their work, each other, and themselves so they can deliver products their customers love and results that matter.”
Chris Diller
What Our Clients Say
“From the very beginning, Chris created a space grounded in trust, respect, and patience—one that allowed for real self-discovery rather than quick answers or surface-level fixes.”
Chief People & Community Officer, Retail Technology Company
More About Me
I began my career in software engineering in 2006, but I quickly discovered that the most powerful "operating system" in any organization is the human one. My leadership style is fundamentally shaped by my experience as a coach -- I view myself as a catalyst, dedicated to holding space for teams and individuals to "unleash their awesome" and deliver solutions their customers love.
At Ecolab and Target, I applied this coach-leader lens to guide teams in large-scale Agile transformations, focusing on how technical shifts could empower people to do their best work. Later, as a Product Director at Blue Cross Blue Shield, I led enterprise-level transitions to a product-led operating model. In these environments, I learned that true operational excellence is born when servant-leadership meets strategic clarity — removing barriers so that high performance and psychological safety can flourish.
This enterprise perspective is balanced by the grit I gained in the entrepreneurial trenches at Reagle Property Management and Movies on the Go. Managing the nuts-and-bolts of these businesses (from profitability analysis and contracts to maintenance and logistics) taught me the resilience and stewardship required to sustain a organization.
Today, as the Operations Leader at The People Side, I blend that entrepreneurial discipline with a coach's heart. I see operations as a support system for growth, building the human-centered infrastructure that allows our tribe of consultants to stay focused on their transformative work.
When I’m Not Working …
When the laptop closes, my world is all about connection with the people around me. On warmer days, you'll find me with my wife and two daughters in the pool, squeezing every bit of summer out of Minnesota, or out hiking in one of Minnesota's state parks (my wife and I are currently on a mission to hike every "Hiking Club" route).
When the weather turns colder, it's game time! When we're sitting around a table and rolling dice, or shoulder-to-shoulder with a controller in our hands, I love the shared experience of play. When I can, I enjoy tinkering on the guitar -- but you're not likely to find me at an open mic night! Come Fall, I am a loyal Green Bay Packers fan.
Life is hectic with two active girls, but we try to take time to be together. When we are watching movies as a family, or snuggling up to read a book (both are currently hooked on Harry Potter), I'm thankful for every moment we share.