
Chris D.
5.0
(6)
Unleash Your Awesome | Experienced Product Director, Coach and Trainer
Studied at University of Wisconsin - Madison
Works at The People Side
Successful clients at
Available Wednesday at 2:30 PM UTC
Questions? Start chatting with this coach before you get started.
Chris's Coaching Offerings
Custom hourly · $345/hr
Get help with Skill Building, Execution, and .
Chris also coaches for Executive Coaching and Leadership Coaching. View all.
Chris’s Product Management Qualifications
Coaches professionally
Experience level: Director of Product
50+ people coached for Product Management
Chris has helped clients get into these companies:
Hi there! I'm Chris - I specialize in guiding professionals to excel in product management roles. As a Product Director in charge of a company-wide transformation effort, I've empowered numerous product professionals and their teams to navigate effective product management and build products their customers love. My background includes pivotal roles such as Director of Product Transformation at Blue Cross and Blue Shield of Minnesota and Sr. Manager of Software Engineering Coaching at Target, where I honed my skills in agile coaching and product strategy. I hold a Graduate Certificate in Executive Coaching from the University of St. Thomas, which complements my technical foundation in Computer Engineering from the University of Wisconsin - Madison. Let's connect to craft a personalized strategy for your product management journey and Unleash Your Awesome!
Chris can help with:
Skill Building
Execution
Strategy & Vision
Influence & Collaboration
Frameworks
Chris also coaches for Executive Coaching and Leadership Coaching. View all.
About Chris
Chris is a Leadership Coach, Fractional Consultant, and Coach Supervisor with experience ranging from non-profit organizations to Fortune 500 companies in fields spanning retail, healthcare, industrial, commercial, and insurance markets. He began his career developing software in 2006, and held various roles including as an embedded software developer, project leader, ScrumMaster, product and agile coach, engineering manager, and product director. The constant through that work has been his ability to help teams and leaders better understand their work, each other and themselves. Chris has a passion for helping individuals and teams “unleash their awesome” to increase their performance, deliver exceptional results, and build products their customer love. Combining his Certified Team Coach certification from ScrumAlliance and his International Coaching Federation Associate Certified Coach credential, he has focused much of his practice on product teams and technical leaders, – but has had a range of team and individual clients from vice presidents and directors, to educators and aspiring entrepreneurs. In 2020, Chris became a Founding Partner of the Center for Coaching in Organizations - a non-profit group focused on accredited executive coach training, workshops, thought-leadership and resources for coaches and organizational leaders. He joined CCO's Board of Directors in July 2021 as Treasurer and moved into the Board Chair role in November 2023. He's taken an active role in planning the Coaching in Organizations Summit and the Executive Coaching in Organizations Coach Training Program, most recently joining CCO's Faculty as an instructor. Chris enjoys being outdoors, playing games of all types, tinkering on the guitar, cheering for the Packers and, most of all, spending time with his wife and two young daughters. He is a graduate of the University of Wisconsin and lives in the Twin Cities.
Why do I coach?
I am passionate about helping teams and leaders better understand their work, each other, and themselves so they can deliver product their customers love and results that matter.
Work Experience

Chief Operating Officer
The People Side
February 2026 - Present

Principal Coach
Diller Coaching & Consulting, LLC
January 2018 - Present
Career Development Coaching and Leadership Development Coaching
Director, Product Transformation
Blue Cross and Blue Shield of Minnesota
November 2023 - December 2025

Sr. Manager
Target
October 2021 - November 2023
Leadership Development Coaching

Lead Agile Coach
Target
January 2018 - October 2021
Leadership Development Coaching
Owner / Property Manager
Reagle Property Management, LLC
April 2012 - April 2020
Owner
Movies on the Go, LLC
June 2008 - April 2018
Education
University of St. Thomas
Graduate Certificate, Executive Coaching
2019 - 2020

University of Wisconsin - Madison
BS, Computer Engineering
2002 - 2005
Activities and societies: Colleges Against Cancer, Relay for Life
6 Reviews
Overall Rating
5.0
Chris has helped clients get into these companies: