Strategic Change

guided by experience.


Partnering with mid-market organizations to navigate mergers, divestitures, and complex transformations with clarity and calm.

Transformation requires more than frameworks

Organizations navigating major change need more than consultants with PowerPoints. They need a strategic partner who understands that every transformation is a human system, not just a project plan. Someone who's led enterprise-scale change and knows how to create clarity when certainty doesn't exist.

Experience The Upside

Steady partnership in uncertain times

Whether you're integrating after a merger, preparing for a divestiture, or restructuring for the future, change at enterprise scale is complex. We bring 25 years of experience guiding organizations through exactly these moments—combining strategic rigor with the calm presence needed when plans meet reality.

About Us

On the Up & Up

Blog Feature!

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Quiet Quitting Part III: “Leading with Empathy”

Up to Speed

updates from the Upside!

  • What Upsiders are saying

    “Upside makes it fun to enact serious change. Their expertise, energy and experiential approach has moved our team forward in ways I couldn’t have imagined. Their partnership is incredibly special to us, and we can’t recommend them highly enough.”

  • What Upsider's are Saying

    “Upside did a wonderful job of tailoring the content to our team to make our time extremely valuable. During our workshop, we had the perfect combination of personal development, team building and fun.”

  • What Upsiders are saying

    “Carolyn is patient and understanding. She creates and maintains psychological safety. Carolyn did a wonderful job of helping me self-reflect and solve for things myself versus telling me what to do.”

  • What Upsiders are saying

    “Carolyn is a great listener, straightforward, truly cares, connected, knowledgeable, skilled, confident, intelligent, and strategic. I love her vision, and she gives great advice when asked. Carolyn is simply the BEST coach and mentor I’ve ever had.”

  • What Upsiders are saying

    “Carolyn has steadiness in her coaching. It is both comfroting and calming and gives me so much confidence in both her coaching ability and our relationship. She’s also very knowledgeable in her coaching craft and has an ability to read the person/situation and call on her past experience + knowledge to fit the given situation.

    I thoroughly enjoy my coaching time with Carolyn. It is truly something that I look forward to when it’s coming up on my calendar. I leave our time together feeling like I have a roadmap - direction to take - and know that I’ll have that accountability for the next time we meet. She has incredible patience when I’m processing my own thoughts, and I can always tell that she genuinely cares about me as a person and my success in my current and future endeavors.”