Creating Collaborative Organizations & Teams

About Chris & Caldwell Creative

I understand the challenges of leading cross-functional teams toward strategic goals. Disengaged employees, resource battles, and delayed, over-budget projects make it tough when solutions aren’t obvious.

I’ve been there. From leading teams at Shopify to building them in my own and others' businesses, I’ve seen how poor collaboration and misalignment stall progress and jeopardize key objectives.

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I founded Caldwell Creative to provide organizations with the tools, skills, systems, and process to transform into collaborative powerhouses.

Jeff Archibald

CEO of Paper Leaf (Exited)

I’ve seen him transform culture and efficiency while building rapport within an organization – often, outcomes that are at odds with one another.

Brian Ragone

Founder & CEO of Puzzle

After a month, his contributions have shaped the entire company vision, culture, and product direction.

How I Help You Achieve Lasting Change

Every day, I wake up excited to help leaders like you transform your organization. My goal is to guide you toward a company that thrives using collaboration as a hard to replicate competitive advantage in your organizational DNA.

In today’s fast-paced world, rapid adaption is key. That’s why I offer evergreen leadership and management solutions that keep your teams agile and ready to respond to challenges without teams burning out. With the right systems, skills, and processes in place, you’ll have a future-proof strategy for navigating change and out competing your competitors.

what you can expect when working with me

I’ll be fully invested in your success

I commit to your goals as if they’re my own, working closely with you to ensure the best outcomes for your business.

Matthew Willox

Technical Director at gskinner

When Chris creates a vision, it is for the company. His visions embody change and the risks that go with it. He puts in the work every day to make them come true.

I listen, adapt, and act quickly

I take the time to understand your unique challenges, then respond with tailored, actionable solutions.

Dave Johnston

Founder & CEO of Omnee

Chris takes the necessary time to weave into your team and truly understand what is needed, then he finds effective ways to fill the gaps.

I foster open communication and trust

Transparency is key—I’ll create an environment where honest feedback is encouraged and acted upon.

Bayli Payne

Head of Partnerships at Puzzle

The exercises were collaborative in nature and he was able to create a safe space for the whole team to problem solve and come to agreement.

I challenge the status quo to drive real change

I’m not afraid to push boundaries, helping you break down barriers and embrace new ways of working that foster growth.

Derek Kadis

Director of Adoption at Omnee

Chris has compiled years of experience with industry knowledge collected from all areas of the tech sector in order to create a very effective methodology.

Here’s how I make that happen:

Leadership and new manager development

Training leaders and managers to operate teams and solve problems with strategic, innovation, and value focused collaboration.

Anne Brown

Design Director at Paper Leaf

After working with Chris, my team broke free from stagnation and the 'this is the way' mindset. I've seen a major shift...

Evergreen change management solutions

Systems designed to reduce change fatigue and prevent burnout while ensuring adaptability.

Lanny McNie

Head of Operations at gskinner

Chris was instrumental for change in the senior team/strategy.

Break down silos in, and across, teams and levels

Collaborative working sessions designed to improve strategy, maximize value, create alignment, and explore problems and develop innovative solutions.

Brian Ragone

Founder and CEO of Puzzle

We work with Chris Caldwell every year for his workshops to get a crystal clear company direction across all teams.

Culture design and system integration programs

Design a culture that aligns with your organizational strategy, aligns decision-making, and differentiates you in market.

Paul Bellows

President of Yellow Pencil (Exited)

His thought leadership on culture, design strategy, and collaboration grabbed my interest immediately.

Employee success, growth, and performance management

People focused systems that align individual and organizational interests for the benefit and success of everyone involved.

Bethani Jade

CX Lead at Omnee

I couldn't have rolled out an on boarding program this fast without this guide.

Become a collaborative company

Tear down silos with collaboration

At the heart of every business challenge is one common thread: misalignment. Whether it’s teams working in silos, disengaged employees, or strategies that don’t connect, these issues hold your company back. I’m here to change that.

With over 20 years of experience leading teams across industries, I combine hands-on leadership with facilitative coaching to help you build an organization where collaboration thrives, strategies align, and your teams are fully engaged.

Let’s work together to transform your business into a high-performing, collaborative powerhouse. Take the first step today and connect with me on LinkedIn.

Connect on LinkedIn