Propel your product, team, and business in the right direction!

As a leader, it's not uncommon to face overwhelming challenges in leading a team, developing products, and building a successful business. But don't worry, I'm here to help you navigate uncertainty, enhance your leadership skills, and achieve clarity, so you can stay focused on your goals.

Your challenges

How I help


Improve your leadership effectiveness, avoid burnout, and navigate the ambiguity and uncertainty that comes with being a founder, leader, and business owner. We’ll work to improve your clarity, focus, and strategy using a simple system to create focus and accountability.


Collaborative workshops drive team progress towards common goals with interactive, dynamic sessions facilitated by a skilled professional to improve communication, foster collaboration, and spur new ideas and solutions.


Bring expertise and objectivity to efficiently discover your product idea's potential, target market, and develop a roadmap. This saves time, increases productivity, and helps you focus on other business aspects while avoiding costly mistakes.


Bring expert knowledge, fresh perspectives, and an understanding of research, ideation, and design best practices to your startup. I’ll help you create a beautiful and useful product that people love.


Strategy Puzzle

Building culture, product, and design foundations at a pre-seed tech startup.

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

Brian Ragone
+32.7% gskinner

Creating alignment and leverage accross teams to improve profitability.

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We essentially eliminated scope creep.

Lanny McNie
Quality Omnee

Improving the outcomes and effectiveness of the product development lifecycle.

Coming soon

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.

David Johnston
25x GoLife

Helping families get access to insurance by streamlining the application process.

Coming soon

I don't think there's anything more you can do to make it easier for tech illiterates... Extremely easy, extremely fast, highly recommend.

Jennifer K.
2x Hendrick Motorsports

Giving the most advanced team in NASCAR a new way to analyze data.

Coming soon

It’s producing a more efficient lap and a faster lap time for me, [...] That can advance you on the track and put you in a race-winning position.

Jimmie Johnson
An image of Chris Caldwell in a hero pose in a cyberpunk environment that was generated by AI. Chris's signature done with a whimsical calligraphic style.

Hi, I’m Chris Caldwell and I want to use my superpower to support you in your journey towards creating an exceptional company, team, and digital product. The kind that differentiates itself in the mind of your customers, investors, and the people who have yet to join you on the path towards success.

Curious about me?

The impact in the future will set our company up for long-term success.

Brian Ragone

When we first started the conversation about working together, it was about you coming in as a potential product leader, but your skillset extends way beyond as a leader and team member...pleasantly surprising!

Dave Johnston

His thought leadership on culture, design strategy, and collaboration grabbed my interest immediately. He's a people leader and a design leader and would be a benefit to any team.

Paul Bellows

Chris is a deep thinker. He’s also a rare combination: a craftsperson turned team leader, someone who actually knows the power of true, people-focused leadership and can execute on that. I’ve seen him transform culture and efficiency while building rapport within an organization – often, outcomes that are at odds with one another.

Jeff Archibald