Get good at the skills design school skipped.

CDO School is an experimental school of interdisciplinary study of business, code, psychology, data, and storytelling.

13+ courses

150+ tools

1:1 coaching

Live weekly events

5 out of 5 stars

“This is a masterclass for experienced designers."

Isaac Steiner
Isaac Steiner
Lead Product Designer, DocuSign

Growing the world’s most strategic design leaders and teams

The hardest challenge you face is convincing non-designers to make better choices.

your day-to-day is filled with friction, pushback, apathy, random questions, or skepticism about your work...

you spend hours painstakingly tweaking, adjusting, and refining your argument, hoping next time it works...

you work directly with stakeholders who have titles above you and the ability to say, "no, thanks"...

And the traditional options to break through aren't great

Figure it out alone and hope for the best

Use your entire budget for a single course or workshop

Join another Slack community that no one talks in

Save another browser tab with that Medium article you'll read someday

Refresh your LinkedIn feed and see the same posts again and again

Switch careers to get a new title while doing the same job

Be honest. You wouldn't be here if things were going according to plan. CDO School offers something new. We teach you how to make business sense, so you can go break it.

Find the spark you've been looking for with the skills to be both logical and cool.

Become business savvy

Communicate effectively with execs

Connect craft to operations

Describe your ROI with data

Measure & track your impact

Design your influence

5 out of 5 stars

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

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

What you'll learn

CDO School isn’t another online course that you’ll buy and forget about. It's lessons, check-ins, cheatsheets, templates, and coaching to help you find momentum now.

We’ll show you what works today and teach you WHY it works based on timeless lessons and lived experience.

Everything starts with our core curriculum ➜ create a strategy for YOU.

Module 1

Outline Your Current Strategy

Understand the fundamentals of Strategy and document your current strategic approach.

  1. Framing "strategy" in the context of this course
    14:36
  2. Rethinking the role of the designer
  3. What is Strategy?
    15:47
  4. The role strategy plays inside a company
  5. Fundamental elements of strategy
    22:08
  6. How companies use different levels of strategy to win in business
  7. Strategy for the product stack
    18:23
  8. How to create good strategies, and how to spot the bad ones
  9. Selling your strategy
    20:15
  10. Applying strategic thinking at each level of your career
  11. Creating a strategy for a challenge you're facing now
    25:32
Module 2

Turn Your Insights into Powerful Arguments

Effectively communicate your strategic insights to stakeholders and peers.

  1. Preparing your pitch
    14:52
  2. Why do companies hire management consultancies and what can we learn from them?
    16:28
  3. What is analytical storytelling and how it is different from narrative storytelling?
    19:15
  4. Tips for when to use narrative vs. analytical storytelling structures in real life
  5. The Pyramid Principle and the Situation Complication Resolution framework
    21:36
  6. A real world, analytical storytelling example - The United States Postal Service
    17:43
  7. Telling a variety of analytical stories with the SCR structure
    20:12
  8. When might we need to show more than one resolution?
    15:54
  9. Using Scenario Analysis for more than one resolution
    18:35
  10. Tips for when to use one resolution vs. several resolutions
Module 3

Know the Direction and Focus of Your Business (or Product)

Get clear on your company's strategic positioning and business direction.

  1. Rethinking innovation
    15:34
  2. Figuring out the strategic direction of your company/product
    18:22
  3. Figuring out the strategic focus of your company
    20:15
  4. Describing your business/product with the strongest shape
    16:42
  5. A deeper dive into Porter's Generic Strategies
  6. The shortcomings of Porter's Generic Strategies
  7. Using your current responsibilities to select your strategic focus for this course
    19:33
  8. Determined the primary direction and focus of your company
    23:10
Module 4

Raise the Impact of Your Work

Maximize the value and impact of your design work.

  1. The Value Proposition of Design
    16:07
  2. What is behavioral design and why is it important?
    18:22
  3. What is behavioral change? And, how is it different from behavioral design?
    17:45
  4. The Fogg Behavior Model
    21:34
  5. Remixing the "The Magic Triangle" approach when Design is the product
    19:12
  6. The Value Model "magic triangle" of my team at USAA
  7. Influencing partner behavior by using behavioral design; A story about a Design System
    22:18
  8. Understand the value you provide to your partners to improve that value; The Good Partner Map
    18:43
  9. All culture or transformation projects are behavior change projects
  10. A walkthru of The Good Partner Map
    24:15
Module 5

Make Your Strategy Actionable with Metrics

Implement new metrics for quality with a practical approach.

  1. Connecting design health to business health
    20:47
  2. Design is the product
    16:32
  3. The Balanced Scorecard Approach and why it's important
    19:15
  4. What are Strategy Maps and what do they have to do with OKRs?
    21:36
  5. Creating a "localized view" of great design with a balanced scorecard approach
    17:43
  6. When OKRs work well (and don't)
  7. Four reasons why we need to expand the OKR framework
  8. Introducing the POKR Framework
  9. Three initial steps to build a Desirability POKRs with Strategy Maps
    22:18
  10. A quick example of creating Strategy Map for Desirability
    18:43
  11. Expand the Desirability POKR model with metrics
    24:46
  12. Hard-earned lessons to help you start measuring
Module 6

Calculate and Describe the ROI of Design

Communicate and get emperical evidence of how design is creating an impact.

  1. Working with business math
    19:07
  2. Demystifying ROI and why that is important
    19:07
  3. Aligning design to ROI math and why that's important
    19:07
  4. An inside-out approach to experimentation
    19:07
  5. Three steps to connect Design ROI to Business ROI
    19:07
  6. Using a scorecard to communicate Design's value
    19:07
  7. What developing design metrics at Apple taught me about communicating the value of design
    19:07
  8. Develop ratings and rubrics to communicate quality
    19:07
  9. Creating Design scorecards from scratch
    19:07
  10. Tips and scripts for applying these lessons IRL
    19:07
  11. How POKRs and Scorecards relate to Targets and every day Tactics (Initiatives)
    19:07
  12. QUICK REFERENCE: Types of product (viability) and customer support metrics to ask about
    19:07
  13. QUICK REFERENCE: A bunch of resources for desirability metrics and measurements
    19:07
  14. Bonus: How DocuSign is creating desirability scorecards from scratch
    19:07
Module 7

Prioritize what to do (or not) now, next and later

Strategic prioritization to connect the day-to-day with the big picture.

  1. Value-based decision making; Actual vs. Perceived value
  2. Defining and demonstrating two fundamental aspects of design with POKRs
  3. The four Perspectives of viability are crucial to remember
  4. Remixing viability POKRs to create organizational POKRs
  5. Adding Metrics, Targets, and Initiatives to our Strategy
    19:07
  6. Prioritize the big picture with a multi-solving approach
  7. Create a backlog of the things you're expected or hoping to influence
  8. Prioritize your next steps with four key actions
  9. Connect your short and long-term priorities with Now-Next-Later strategy maps
  10. Demonstrating how to use ERRC to prioritize actions
    22:15
  11. Combining SCR, POKRs, and ERRC to create better arguments
    23:43
Module 8

Find the ideal Collaborators and Stakeholders to champion design

Get good at stakeholder management and indentify the specific collaborators who will champion design.

  1. The 2x2 matrix is the favorite tool for executives
  2. The 2x2 matrix is quite imperfect and heavily bias
  3. The importance of prioritizing your emotional energy with powerful stakeholders
  4. Using meaningful opposites to identify the stakeholders to invest your emotional energy into
    24:46
  5. Examples of meaningful opposites
  6. Strategically gather evidence for work that creates meaningful impact
  7. Strategically find your Sidekicks, Champions, and Challengers
  8. Promote healthy, effective change while meeting day-to-day expectations; Layering 2x2 matrices
    21:15
  9. QUICK REFERENCE: The VSDR matrix
  10. QUICK REFERENCE: Stakeholder Mapping
  11. QUICK REFERENCE: Evidence For Impact Matrix (VDSR + Stakeholder Map)
Post Course

Post Course Challenges: Put everything together in real life

Apply all the course concepts in practical real-world settings.

  1. CHALLENGE: Update your strategy
  2. CHALLENGE: Communicate your strategy with SCR
    24:46
  3. CHALLENGE: Final reflection

How it works

You’re busy. We get that. CDO School is open 24/7 with flexible learning modes and formats to match you where you are.

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.

5 out of 5 stars

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

Gene Moy
Gene Moy
Senior Manager, UX aPriori Technologies

CDO School is for experienced designers and leaders

Senior, Lead, and Principal Designers looking to drive quality.

Managers, Directors, and Heads driving maturity at scale.

Service Designers, Reaseachers, and DesignOps'ers connecting the big picture to day-to-day tactics.

5 out of 5 stars

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

Ashley Pfeiffelmann
Ashley Pfeiffelmann
UX Director, Celerity

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

[ An open letter to experienced designers ]

I help you make things happen, no matter what the business thinks.

Before I started working with designers and design teams, I was a designer, led design teams, and became an executive.

I designed products and services at Apple, Comcast, and Sony. I’ve built and led teams at Electronic Arts (twice) and Nestlé. I was a corporate strategy executive at USAA. At some point in my career, I likely had the same responsibilities you have today.

I designed, became a boss, a boss of bosses, and then led organizations. And each time I was promoted, I was told, "You’re a quick learner. We expect you to figure it out."

I did figure it out, but the hard way, through a lot of trial and error, mistakes, and self-doubt. Not because that was how I wanted to learn but because no one gave me any other choice. And as I found out, this path is exclusive to me and my career.

CDO School offers something better.

Your challenges and needs are unique because you're a designer. You often have no one to turn to. I fill that gap. I help you with the things you don’t have the time or the experience to do.

I share the systems, playbooks, frameworks, and lessons I wish I had. You get all the benefits of my experience and expertise without trying to choose one cohort or learn on someone else's schedule.

Whether framing your vision in a way people listen to, figuring out a strategy for your team, navigating stakeholders, predicting where and how you can succeed, clearly describing the ROI, growing the skills of your people, communicating effectively with the C-Suite, or all of the above, I specialize in providing real-world value when you have a short-time need.

5 out of 5 stars

“The pace and size of activities was bang on. The content is original and not spoon fed. It really challenged me to think!"

Owen Hodda
Owen Hodda
Design Practice Lead, ANZ

A format to become more engaged, discover breakthroughs, and have FUN!

Practical strategies to help you adapt to change

Actionable skills that work now and tomorrow

Career growth on your terms

What experienced designers are saying:

Pricing

Basic 🌿

Courses + Events + Tools

$499 /year
  • 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?