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](https://thecdo.school/content/images/2024/10/jessica.jpeg)
“I cannot recommend this enough for getting to the next level in your career.”
![Ashley Pfeiffelmann](https://thecdo.school/content/images/2024/10/ashley.jpeg)
“This has all the things nobody tells you about and exactly what I needed.”
![Ariba Jahan](https://thecdo.school/content/images/2024/07/ariba_2.jpeg)
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](https://thecdo.school/content/images/2024/07/gene.jpeg)
“This has given me the time and space to mature my perspectives.”
![Carolina Tod](https://thecdo.school/content/images/2024/07/carolina_2.jpeg)
“The experience and learnings have fundamentally changed the way I work.”
![Justin Hoyer](https://thecdo.school/content/images/2024/10/justin_hoyer.jpeg)
Hi. I'm Ryan.
![Ryan Rumsey](https://thecdo.school/content/images/2025/02/41-Square-copy-2-f4ae59c6313c2041.png)
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](https://thecdo.school/content/images/2025/02/family-11fe8a073f0d0b02.jpg)
![Design Leadership Summit 2025](https://thecdo.school/content/images/2025/02/F5394C83-9CE5-4F77-97D5-145A8BDAFD64_1_102-048aa26c199058b5-2f40ae130e9d69b4.jpeg)
![Design Leadership Summit 2025](https://thecdo.school/content/images/2025/02/85C9181B-ED9E-464B-A493-77BB09C31AD9_1_102-3c5499fd4f3bb543.jpeg)
![Author of Business Thinking for Designers](https://thecdo.school/content/images/2025/02/slide_3-d801e661bdb17a70.jpg)
![I lead workshops](https://thecdo.school/content/images/2025/02/6EE71E25-35E5-49DF-8254-6CF519548685_1_105_c-91b5b4856817332e.jpeg)
![North Star Strategy Maps](https://thecdo.school/content/images/2025/02/1707588890103-3b8fa016a7cdee7a.jpeg)
![Small talks](https://thecdo.school/content/images/2025/02/CA403261-5731-4B7E-A907-808BEC84A477-1efaa749e4b99300.jpeg)
![Resource Library](https://thecdo.school/content/images/2025/02/1E66BBD3-61AE-474A-B862-0B8F4EBFCBC7_1_105_c-6d749d123a538ed9.jpeg)
![Daily Audio Tips](https://thecdo.school/content/images/2025/02/maxresdefault-ed6f755b12341630.jpg)
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
13+ on-demand courses
Pragmatic. Effective. Systematic. Take one of our popular courses to multiply your effectiveness in business, and see yourself within it.
Live role-playing cohorts
Participate in real-world scenarios (negotiating, persuading, measuring, etc.) and get opportunities for critical observation and feedback from peers.
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+ 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.
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.
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
Because some of the best lessons come in small packages, our audio tips are less than 3 minutes long, and delivered Monday thru Friday.
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.
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
- 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
Pro 🪴
Basic 🌿 + Live Cohorts + Coaching
- Everything in Basic, plus:
- Live Role-Playing Cohorts
- Real-world simulations
- Practice specific leadership challenges
- Receive feedback
- Private group of peers
- Asynchronous 1:1 coaching with Ryan Rumsey
- Ask questions about your situation
- Get a written response within 48 hours
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.