Become Undeniable. Unleash Your Potential.

CDO School is a new playbook for design leaders—for a new business reality.

Learn to navigate both the skills and the personalities that shape business decisions. Get 13+ courses, 150+ tools, live workshops, and 1:1 coaching to supercharge your career.

Growing the world’s most strategic design leaders and teams

Trying to lead design forward in this new business reality is hard… if you're figuring it out alone.

You waste time looking for the perfect answer.

You pay premium prices for courses that barely scratch the surface.

Your deepest questions go unanswered.

You learn skills that don't change power differentials.

Your confidence plateaus or (worse) dips.

You're left questioning your career path.

And that leads to sleepless nights and feeling constantly overwhelmed. I don’t want that for you. CDO School has given thousands of design leaders a superpower: Agency. CDO School will work for you too.

Expand your clarity

CDO School teaches the skills that distinguish world-class design leaders from the rest: strategic foresight, business savvy, and effective communications.

“It's an eye-opening and really helps you to map design to the way executives think.”

Jessica Romeo
Jessica Romeo
Experience Strategy Directory, Firefly Health

“I cannot recommend this enough for getting to the next level in your career.”

Ashley Pfeiffelmann
Ashley Pfeiffelmann
Head of Transformation, North America, Anomaly

“This has all the things nobody tells you about and exactly what I needed.”

Ariba Jahan
Ariba Jahan
Head of Transformation, North America, Anomaly

Grow in five key areas: Business Acumen, Strategic Foresight, Relationship Building, People Development, and Executive Presence.

Become business savvy

Communicate skillfully with execs

Connect craft to operations

Describe your ROI with data

Measure & track your impact

Raise product & service quality

13+

on-demand courses

150+

tools and templates

50+

Figjam canvases

30+

mini-guides

200+

lessons

300+

hours of video content

20+

original frameworks

50+

live events per year

100+

3-minute audio tips

“In short, CDO School is the best money I have spent on my career.”

Gene Moy
Gene Moy
Senior Manager, UX aPriori Technologies

“This has given me the time and space to mature my perspectives.”

Carolina Tod
Carolina Tod
Manager of UX and Product Design, Fintech Magalu

“The experience and learnings have fundamentally changed the way I work.”

Justin Hoyer
Justin Hoyer
Service Design Lead, NTT

Hi. I'm Ryan.

Ryan Rumsey

I made my way up from Designer to Executive. I worked in Design Led- companies. I transformed Design Immature orgs. Now, I'm an Entrepreneur, Author, and Founder.

Over the last 25 years, I designed software at Apple. I built and led in-house teams at EA, Nestlé and USAA. I’ve presented and led workshops around the world. I've delivered in-house training to small teams, and for huge multinational companies. My book Business Thinking for Designers has been read by 60K people. I coach some of the best design leaders in the business. And, I teach everything I know to help you position design to win.

Everything begins and ends with these four people
Design Leadership Summit 2025
Design Leadership Summit 2025
Author of Business Thinking for Designers
I lead workshops
North Star Strategy Maps
Small talks
Resource Library
Daily Audio Tips

How to CDO School

CDO School takes a different, fresh approach to career developlent. Our focus is to teach you skills and coach you through your biggest challenges at work: people and power. Our format allows you to become more engaged while having a meaningful journey.

1

Join CDO School

Get access to all our on-demand courses, member-exclusive events, and personalized coaching.

2

Start learning

Discover the fundamental skills you’ll need to represent the design as part of a larger ecosystem and help you build your influence beyond design itself.

3

Grow Your Career

With a plan, you’ll be amazed at how your confidence skyrockets, those overwhelming feelings subside, and how design’s relevance to business expands.

Design Leaders love CDO School!

CDO School is perfect for…

Senior, Lead, and Principal Designers looking to move into management.

Managers, Directors, and Heads who lead teams and disciplines.

Service Designers, Reaseachers, and DesignOps'ers who work across teams.

What you get when you enroll

On-Demand Courses

13+ on-demand courses

Pragmatic. Effective. Systematic. Take one of our popular courses to multiply your effectiveness in business, and see yourself within it.

Design Leadership Role-Playing with Peers

Live role-playing cohorts

Participate in real-world scenarios (negotiating, persuading, measuring, etc.) and get opportunities for critical observation and feedback from peers.

1:1 Design Leadership Coaching

Personalized 1:1 coaching

Personalized guidance and support when you need it to help you gain valuable insights and overcome challenges specific you and your role.

30+ quick guides for Design leaders

30+ step-by-step plays

Designed to bring leadership out of thinking and into action, these custom, step-by-step activities are perfect for bringing meaningful change to life.

Live Events

Weekly events & replays

From Drop-in Office Hours to Manager Circles, our calendar and workshop replays are made to fit your busy schedule, not compete with it.

Resource Library

150+ tools & templates

Bring your biggest lessons back to work with you with our custom Figma, Mural, Miro, Google Sheets, Docs, and PDF templates and tools.

Daily Audio Tips

Daily audio tips

Because some of the best lessons come in small packages, our audio tips are less than 3 minutes long, and delivered Monday thru Friday.

CDO School Design Strategic Leadership Playbook

130-page activity guide

A 130-page activity guide to interpret your business strategy and choose the unique, specific ways your Design Team brings good business to life.

CDO School Design Leadership playbook

The CDO School Playbook

Examine the Four Fits of Design Value, and repeatedly give you yourself the time, energy, and deliberate effort position design to win at your company.

CDO School is the system to lead effective design. Our flexible courses, live events, and 1:1 coaching are perfect for accelerating your career.

Practical strategies to help you adapt to the constant change inside your company

Actionable skills that work now and tomorrow

Career growth on your terms that fits your busy schedule

Make good things happen with the expertise you already have

Struggling with how business, design, metrics, influence, and confidence all fit together?

Paying a premium prices for abbreviated course?

Learning disconnected skills that don't build on each other?

Having the same stale arguments about your value?

Your career needs CDO School.

CDO School is for mid-career designers, not seasoned executives. For continuous learning, not quick fixes. It's all about practical content, and actionable knowledge to thrive in this new era of business.

Pricing

Basic 🌿

Courses + Events + Tools

$499 /year
Get started
  • Access
  • All courses ($2400 value)
  • All workshops ($297 value)
  • 150+ Tools & Templates
  • 30+ Actionable Plays
  • 130-page Workbook
  • Past event recordings
  • Daily Audio Tips
  • Weekly Drop-in Office Hours
  • Expert and member-led events
  • Completion certificates

FAQs

Why should I join CDO School when there are other design leadership programs?

It's so great that designers and design leaders have options these days to learn about business, communication, management, and influence. Most of these programs do a good job of teaching you how to fit design into the status quo of business - how to speak the language, how to be visible, and how to describe your work. But that's not what drives change.

CDO School is fundamentally different. We teach you how to make design unignorable by building evidence, moving faster than bureaucracy, and showing value in unexpected ways. This isn't about getting a seat at the table. It's about changing the game entirely.

Why choose CDO School over a live cohort on Maven or other platforms?

The traditional path to design leadership learning usually involves piecing together lessons found in multiple courses. At $500-2k each, you'd need to invest over $10k and months of scheduled sessions to get the full picture. Plus, you're locked into instructor timelines, have to take time off work, have limited access to the instructor, and can't easily revisit the material when you need it most.

CDO School provides the complete playbook, ready when you are, for as low as $499. You get immediate access to everything, can learn at your own pace, and apply the tools to your real work in real time. But the bigger difference? This isn't about attending classes. It's about having a proven playbook and personal support when you need it most.

I already understand business basics. What makes this different?

Knowing business fundamentals isn't enough anymore. The real skill is knowing when business decisions are actually business decisions – and when they're emotional ones masquerading as business logic.

CDO School teaches you how to spot the real roadblocks, build the right evidence, and focus your energy where it matters. Business programs leave out your biggest challenge: building relationships and trust with people who are skeptical of what you do. This isn't about learning business terms or frameworks. It's about learning to win in ways you haven't figured out yet.

What if I'm not sure I want to be a CDO or executive leader?

The insights and strategies in CDO School aren't just for people pursuing executive roles. They're for anyone who's tired of seeing good design work die in endless meetings and politics. Whether you're a Senior Designer wanting more influence, a Design Manager trying to protect your team from bureaucracy, or a Director attempting to create real change - this is about having impact. We show you how to adapt, adjust, and position design to win in ways that are specific to your situation.

How is this different from traditional Design or DesignOps training?

This isn't another prorgam about workshops, journey maps, or design systems. Those are important tools, but they haven't fundamentally changed design's influence in most companies. CDO School is about what happens before the frameworks and processes – how to spot real opportunities, how to build evidence that can't be ignored, and how to move faster than the bureaucracy.

With AI democratizing so much of development and operations, we show you how to focus your energy on the work that actually creates change. This is about being dangerous – in the best possible way.

What if my company isn't design-driven?

Here's the reality most programs ignore: most companies don't compete on design. They win through pricing, scale, network effects, or enterprise sales. Instead of fighting this reality, CDO School shows you how to use it to your advantage.

You'll learn how to demonstrate exactly how design can amplify existing advantages, make current strategies stronger, and create unexpected value. This isn't about converting everyone to design-first thinking. It's about making design an undeniable multiplier of what already works, and commanding attention for what doesn't.

Ready to awaken, refresh, and activate your career?