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.