Helping early stage founders and leaders

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

You need a system for managing team performance, setting goals, and providing feedback and coaching.
You have an idea for a software product and don’t know where to start.
You’re struggling to develop an innovative and differentiated software product that people love using and want to pay for.
You need to create a compelling culture to attract and retain the best employees.
You want to stay bootstrapped, remain profitable, and avoid taking on external funding until absolutely necessary.
Your team keeps asking you about decisions they should be able to make on their own.
You want to stop working 80+ hours a week and give your team ownership, autonomy, and accountability.
You want to spend more time doing strategy work, but can’t figure out how to step away from the day-to-day.

How I help

Coaching

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.

Workshops

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.

Consulting

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.

Design

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 will love using.

Outcomes

Profitability +32.7% gskinner

Creating alignment and leverage accross teams to improve profitability.*

Learn more

We essentially eliminated scope creep.

Lanny McNie Policies issued 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. Turnaround time 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 *Work was completed while I was Head of Design at gskinner

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?

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

Need an introduction?

Schedule a complimentary call

Are you struggling to unlock your team's true potential? Do you feel like there are challenges hindering your team's success? If so, I can help you!

Book a no-commitment call with us today, and take the first step towards achieving your team's true potential. During this conversation, we will discuss your team and business struggles, and provide guidance and support to help you overcome these obstacles.

Don't let your team's potential go to waste! Book a complimentary call and let me help you achieve greater success.