Design Thinking Roundtable

A community for strategic design and innovation leaders in established organizations.

A client being hands-on as we map out together all the things their custom software needs to do.
Participants at an event at Highland's Chicago offices share their expertise with the community.

Does this sound like you?

You lead digital experience, experience design, and innovation in a company that isn’t used to working this way.

You wear a bunch of hats: practitioner, team leader, executive-whisperer, change agent.

You’ve been asked to create a new way by an organization that--at the same time--is regularly trying to kill off or compromise your work.

You love your work, your team, and the change it represents, and get a bit worn down by the scale and bureaucracy of an older, established company.

You're looking to connect with a community of like-minded leaders facing similar challenges who are willing to share helpful advice based on decades of relevant experience.

Ready to become a better leader and transform your organization?

The Design Thinking Roundtable helps build connections, share insights, and provide a support network for leaders who share similar goals, similar values, and are tackling the same tough obstacles in creating organizational change as design thinking practitioners and leaders.

The heart of the Design Thinking Roundtable experience is a cohort-based learning model.

  • Each cohort is 6 months long and intentionally capped at 6 participants.

  • Each participant is a Director / VP-level leader or above in a large, established organization, tasked with leading an experience design or innovation function.

  • All participants are specifically invited and/or go through an application process.

  • You’ll participate in monthly meetings rotating to each participant’s office, where we will focus on the challenges and opportunities that are unique to that organization as well as explore topics of interest as determined by the cohort.


Applications for Fall 2019 and Spring 2020 cohorts are now open!

  • Our Fall 2019 cohort will take place between September 2019 - February 2020

  • Our Spring 2020 cohort will take place between April 2019 - October 2020
Apply Today

About the Facilitator

Jon Berbaum

All Design Thinking Roundtable meetings are facilitated by Jon Berbaum, President of Highland Solutions.

Jon joined Highland in 2007 and has led a variety of experience design, digital strategy, and innovation initiatives for Highland’s clients. As Highland has increasingly partnered with innovation and design leaders in large, established organizations, Jon has developed a particular interest in--and sympathy for--the unique challenges faced by these leaders, and the lack of constructive community for leaders in similar roles across companies.

Connect with Jon on LinkedIn

With the Design Thinking Roundtable, you will:


Connect: Take part in monthly confidential meetings with 6 experienced leaders with backgrounds in design thinking, innovation, and technology.


Network: Expand your community of Chicago-area leaders who can support the success of your organization and your own professional growth.


Grow: With the support of your cohort, you will work together toward the common goal of transforming your organizations through design thinking and innovation.


Applications for Fall 2019 and Spring 2020 cohorts are now open!

  • Our Fall 2019 cohort will take place between September 2019 - February 2020

  • Our Spring 2020 cohort will take place between April 2019 - October 2020
Apply Today

About Highland Solutions

Highland Solutions logo.

Highland Solutions is a digital experience agency with a fierce commitment to keeping people at the center of our work.

We use our skills in CX strategy, custom software development, and CRM implementation to help innovative leaders understand their customers and take smart risks. We love working with customer-centric, mission-driven organizations who want to adopt the principles of more disruptive businesses to take their impact to the next level.