Chief Design Officer School
The CDO School Toolkit

Learn Business. Apply it to Design. Win.

Tired of executing other people's ideas? Master the tactics that work on any stakeholder: the ones who decide without you, those who see design as polish, and the execs asking you to "prove it."

Six years of teaching, refined with 2,500+ designers. A complete library of frameworks, templates, and strategies you'll actually use.

$397

One payment, lifetime access

What's included?

  • 3 courses
  • 30+ Figjam Boards
  • 80+ AMAs & Workshops
  • 70+ audio tips
  • 3 books

How do I get it?

After you purchase, you'll be emailed a private link for access.

Where teams send their designers to learn advanced business tactics

Ryan Rumsey

I'm Ryan Rumsey. I've developed the most advanced system for designers to win at business.

I've heard from so many people who think CDO School is only for designers in senior management roles. That's simply not true.

CDO School is where a design executive (me!) teaches designers at any level (you) the skills most senior leaders won't share. And I do it in a way that's actually exciting and fun.

CDO School is for anyone who's tired of seeing good design work die in endless meetings and politics. This toolkit shows you how to adapt, adjust, and grow from where you are now to where you want to be. The lessons and resources are built specifically to help you learn when you're in the place and mindset to learn.

When I worked at Apple, I learned what it meant to be surrounded by people who encouraged me to push my skills and the practice of design forward. I felt the power of learning when it came from a place of excitement rather than anxiety. And that became the real secret behind my career growth.

Here's what I discovered: my ability to influence decisions and raise my impact at work was not simply because I learned a few business skills, but because I was encouraged to find fun, exciting, and new ways to do business.

Throughout my career, I sat in the rooms where budget cuts and strategic pivots got decided. I saw firsthand why some design initiatives got funded and others got cancelled. In every role, gaining influence required something different–something they don't teach in design or business schools. It comes from seeing your work and the people you work with in a new way.

I'm not a design educator who's teaching design theory. I'm not a business consultant who ignores the power of creativity. I'm someone who's lived both sides of the equation at the highest levels. This particular body of work took six years to build and refine.

I built this toolkit specifically for designers to help you grow your career and win in business in a way that works for you. While they might never get design, this toolkit will help you win anyway.

Take your design career to the next level with tactics you'll use daily.

This isn't another course. It's every method, framework, tool, and strategy I've developed to help designers turn their decisions into business outcomes that matter to people writing the checks.

The Strategic Designer

8 Modules, 109 Lessons
Modules
  1. Welcome to The Strategic Designer
  2. Present Ideas That Get Approved
  3. Decode Your Company's Goals and Priorities
  4. Win Over Hesitant Stakeholders
  5. Prove Design Has Impact with Business Numbers
  6. Create Your Design Scorecard for Leadership
  7. Navigate Pushback and Get What You Need
  8. Balance Quick Wins with Long-Term Goals

Design Org Strategy

9 Modules, 137 Lessons
Modules
  1. Capture the Elements of Your Current Strategy
  2. Present Ideas That Get Approved
  3. Know the Direction and Focus of Your Business (or Product)
  4. Raise the Impact of Your Work
  5. Make Your Strategy Actionable with POKRs
  6. Connect Your Work to Business Math and ROI
  7. Prioritize what to do (or not) now next and later
  8. Find your Sidekicks and Champions while managing your Challengers to meet your goals
  9. Post Course Challenges - Put everything together in real life

The 21-day Influence Challenge

Foundation Week
  1. Organization and Format
  2. Communication Style Self-Assessment
  3. Create a 30-Second Value Statement
  4. Practice Message Delivery with Different Tones
  5. Practice Explaining a Complex Work Concept
  6. Ask for Communication Style Feedback
  7. Create Your Communication Confidence Signals
  8. Record a 1-Minute Professional Video
Connection Week
  1. Practice Active Listening and Summarizing
  2. Prepare Open-Ended Questions
  3. Create a Stakeholder Empathy Map
  4. Strategic Relationship Building Outreach
  5. Script a Difficult Conversation Opening
  6. Email Improvement Exercise
  7. Create a Compelling Presentation Opening
  8. Reframe a Request Using Situation-Complication-Resolution
Influence Week
  1. Craft a 2-Minute Design Concept Story
  2. Practice Your Executive Elevator Pitch
  3. Identify Shared Interests for Negotiation
  4. Plan a Strategic Visibility Action
  5. Identify Influenceable Stakeholders
  6. 30-Day Communication Development Plan
  7. Your Influence Audit: Measure Your Growth
  • Self-Paced Courses
  • Books
  • Business Thinking for Designers
  • Play Up Your Impact
  • Design Your Winning Org Strategy
  • 30+ Figjam Boards
  • 80+ AMAs & Workshops
  • 70+ audio tips

Take a closer look

Foundation Layer: Business Thinking Mastery

  • Complete Business Thinking course that started it all
  • Stakeholder mapping and influence strategies
  • ROI frameworks designed specifically for design decisions

Evidence Building Tools

  • Metrics and measurement approaches that actually move executive teams
  • Case study methodologies that turn project work into portfolio gold
  • Templates for presenting design impact in business language

Advanced Leverage Strategies

  • Organizational navigation for collaborative roles
  • Executive communication frameworks
  • Access and influence building tactics

Real World Application

  • Video replays from live problem-solving sessions
  • Templates refined through thousands of hours of use
  • Audio insights from working with designers and team at Google, Zillow, and Uber

Behind-the-Scenes Material

  • Conversations and context that make everything else work
  • Methodologies for adapting these frameworks to your specific environment
  • The thinking behind the thinking

Ryan Rumsey’s Personal Resource Library

  • Proven business strategy frameworks
  • Figjam templates you can run a workshop with tomorrow

There's a reason designers keep referring their friends to us

This is a resource you'll come back to time and time again.

Six years of material, tested with thousands of design leaders, refined through direct application with teams at Fortune 500 companies. There's no one else selling a complete professional compendium like this because there's no one else who's built one.

Compare to the alternatives:
Business MBA courses: $150,000+ and 2+ years
Executive coaching: $200/hour ($10,000+ for comparable guidance)
Corporate design training: $3,000+ per person for basic workshops
Cohort courses: $1000+ for set times and schedules

Most learning is static. This toolkit is adaptive. These lessons are built to guide you to more confidence today, and help you adjust to new challenges tomorrow.

FOR INDIVIDUALS

$397

One payment, lifetime access

No recurring subscriptions. No forced community. No artificial progression. Just the complete collection of tools you'll reference throughout your career.

FAQs

How is this different from CDO School memberships?

In addition to the Toolkit, Memberships are annual subscriptions that include live cohorts, community events, and quarterly 1:1 coaching calls with Ryan.

What if I bought a CDO School membership?

All members receive access to this material with lifetime access in addition to other membership benefits.

I'm not a design lead/manager/director. Is the Toolkit right for me?

Yes. I've redesigned this training system with multiple entry points for different experience levels. If you're a senior designer or individual contributor thinking "I'm not ready for leadership content yet," start with the Business Thinking Fundamentals path. This builds your confidence and skills before advancing to strategic frameworks. The training works whether you're aspiring to leadership or want to build business influence in your current role.

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 vs. 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.

Isn't this just for people who want Chief Design Officers?

In hindsight, CDO School is a terrible name because let's face it, very few people actually want to be a CDO. This toolkit is for anyone who's tired of seeing good design work die in endless meetings and politics. This is a system that shows you how to adapt, adjust, and grow from where you are now to where you want to be.

More Questions?

Email me directly: ryan[at]thecdo.school

I read everything. If you're not sure this is right for you, or if you need to understand how this fits your specific situation, just ask.

Ryan Rumsey signature

Ryan Rumsey
Founder, CDO School