Casey Woo

Cohort 1

In early-to-mid-stage companies, strategic planning can feel like trying to make 1 + 1 equal 7. The board wants to rule the world, the CEO has a grand vision, marketing needs budget, engineering is fighting for resources, and finance needs to hit certain margins. What do you do? Textbooks and playbooks seem great in business school, but they fall apart when faced with competing priorities and rocketship growth. This course is your roadmap to leading successful strategic planning in a rapidly scaling startup. You'll learn how to create a clear strategic roadmap, disagree and commit with limited resources, prioritize initiatives that truly drive growth, and ensure your team stays aligned and accountable. By the end of the course, you’ll be equipped to lead with focus, foster buy-in from key stakeholders, and implement robust performance management systems that keep your team on track. What to expect:﻿This course is tailored for operators at high-growth startups that need to move quickly and stay agile. Casey is a battle-tested operator who has successfully navigated guiding companies from pre-seed to pre-IPO. Through his work with Operators Guild, he’s immersed himself with top talent and draws from over 20,000 hours of interviews with the world's best leaders. Learning from Casey gives you direct access to someone who’s been in the trenches, understands the challenges of scaling, and knows how to achieve sustainable growth. You'll benefit from engaging in 90 minutes of interactive sessions, allowing real-time feedback and peer learning. You’ll also explore proven frameworks and practical examples focusing on dynamic business alignment rather than static, function-first approaches. By the end of this course, you’ll: • Know how to balance “perfect” with “good enough” for effective, flexible planning • Be able to craft a plan that works, while avoiding death by meeting • Have the confidence to develop and execute a strategic plan that aligns with your company's growth objectives and adapts to its evolving needs. • Know how to identify and focus on the initiatives that truly drive growth. • Understand how to foster buy-in from key stakeholders and maintain alignment across your team. • Take away practical frameworks and tools that you can immediately apply to your own organization to drive strategy, foster alignment, and maintain flexibility.

Strategic Planning that WORKS

Course syllabus

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Tuesdays & Thursdays

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May 7, 2022

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Weekly projects

Course schedule

Senior operators at hyper-growth startups who need to drive and manage rapid scaling efforts.

Strategic CFOs looking for practical, actionable strategies to align teams, prioritize initiatives, and optimize resources.

Forward-thinking leaders who want to dive into annual planning and ensure sustainable growth with robust performance management.

Who Should Take this Course?

What You'll Learn

We'll walk you through a framework that teaches you how to craft a 3-5-year roadmap that aligns your team and propels your company forward.

Set a Clear Vision

Get real-world examples for prioritizing goals at hyper-growth startups. We'll help you identify and focus on high-impact initiatives for your business that drive growth, while cutting out distractions.

Prioritize What Matters

Get insight into resource allocation and effectively aligning teams across the business. Leave with frameworks to ensure you have the right resources in place, and the confidence to know when to pivot if you don’t.

Manage Resources Effectively

Find out what tools and systems work best for other companies at similar stages, and get ideas for implementing performance systems and KPIs that keep everyone accountable and on track.

Track and Measure Success

Get the tools and strategies to crush strategic planning and effectively scale hyper-growth, early-to-mid-stage companies.

Rethinking the Myth of Perfect Planning for Startups

CEO @ Operators Guild. 7x COO/CFO with 20+ years in high-growth tech.

Truth: Planning is about alignment—Learn how to get your team on the same page and navigate unpredictable growth.

Myth: Planning is about setting goals and budgets

Truth: Every forecast is wrong. They force teams to talk, align, and adjust, which is where real progress happens.

Myth: Forecasts need to be accurate

Planning in a startup is messy, dynamic, and anything but linear. Learn how to adapt to changes and seize opportunities

Learn directly from Casey Woo

Casey Woo

Courses

Strategic Planning: How to Scale a Hyper-Growth Company

Lightning Lessons

Rethinking the Myth of Perfect Planning for Startups