Companywide Planning for Startup Leaders

2 Weeks


Cohort-based Course

Lead quarterly or annual planning like a top startup: build coherent strategy, lead the planning process, and set your team up to hit goals

Hosted by

Shaina Anderson

Ex Yelp Chief of Staff, 8x team builder, 10+ year Silicon Valley startup leader

Course overview

Get live peer feedback as you level-up your approach

Join a group of your peers for this 2 week workshop that's taught live, and includes a private community.

Designed for startup founders, execs, and Chiefs of Staff


You facilitate strategy discussions, but your resources feel murky and full of jargon. You're tired of strategy sessions going nowhere.


You lead companywide planning, and need a new approach to manage your growing complexity. You need new methods to wrangle the process.


You're sick of 20 meetings on the calendar, but don't quite know how to meet your goals without all of them. You need focus.

What we'll cover in this workshop

Develop coherent strategy

Great planning starts with clear, well reasoned strategy. With lessons from top strategy guides, you’ll learn that at its core, strategy is about making choices to solve a problem. You’ll leave with a proven outline on how to guide your team.

Guide your company through a planning period

Turn that strategy into actual plans. With inspiration from big companies like Postmates and Yelp, and smaller startups like Fleek and Chewse, learn the key choices leaders make in designing companywide planning. You'll leave with a first draft for your next planning period.

Design a system to hit those goals

An "Operating Cadence" is the system smart teams use to keep everyone focused and accountable on what really matters: It's a thoughtful mapping of what you want for and from your team, and how you'll elicit it. Leave with your first draft to take back to your team.

Benefit from real-time peer feedback

Leadership can be lonely, but you're not in this alone! This workshop is taught live, with your peers attending live with you. You'll get real-time feedback through demos, working sessions, and community chat.

Meet your instructor

Shaina Anderson

Shaina Anderson

Former Yelp Restaurants Chief of Staff, 10+ year Silicon Valley startup leader

I've been in your shoes: You have a giant vision, limited resources, and a growing team to wrangle. I've learned that a coherent strategy linked to solid planning is critical to solving your biggest problems.

  • Inside Yelp (NYSE: YELP), I was Chief of Staff for Yelp Restaurants, transforming our group's approach to planning during COVID's wild ride.
  • I held 4 different leadership roles at Chewse from Seed through Series B, as we raised $40M in VC and were acquired.
  • I launched the partnerships team at Outstanding in the Field, driving work with Visa, Coachella, Bono's (RED), and more.

I believe that once you understand the core elements of strategy and planning, you can flex them across a big range of situations -- as your team grows and your needs change, these first principles will continue to serve you.

  • I’ve managed strategy for teams of 5 to 300.
  • I’ve built 8 teams from scratch across 3 states, from Sales and Success, to Delivery Operations and City Expansion.
  • I’ve lead planning at Seed, Series A, Series B, Public, bootstrapped, and nonprofit companies alike.

I’m a Chief of Staff Fellow at OnDeck, and Mentor for First Round Capital. My work's been in the New York Times, TechCrunch, Food Network, Rolling Stone, and more.

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See what people are saying

        Unquestionably, I’ve learned more about strategy from Shaina than any other person in my career. If you care about a clear path to solving your company's biggest problems, then this workshop is a requirement.
Sanket Agarwal

Sanket Agarwal

CTO and Co-Founder, Fleek
        Shaina got my team to perform at their highest level. Her superpower is the ability to combine a thoughtful and comprehensive process while also creating an environment that builds trust and authenticity in the team.
Cliff Cate

Cliff Cate

VP and General Manager, Yelp Restaurants
        As my Chief of Staff, Shaina accelerated Yelp's growth by getting leaders to the heart of our problems - fast. I've taken Shaina's approach straight to my team at my new startup Lumo, and it's already paying off.
Devon Wright

Devon Wright

CEO and Founder, Lumo; Former Yelp General Manager
        Shaina has an incredible, action-oriented framework for any problem she tackles. From partnerships to operations, she has a gift for aligning teams and getting them to move in a focused way and quickly.
Tracy Lawrence

Tracy Lawrence

CEO and Co-Founder, Chewse
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Workshop syllabus


Module 1: Demystify strategy

All great planning starts with strategy. It's the foundation for your team's goals, plans, and execution.

  • Part 1: Become an expert on good vs bad strategy, and assess your team's current approach.

  • Part 2: Adopt methods to facilitate strategic planning, and build an outline to lead your team with.


Module 2: Tame the planning and goal setting process

Before you jump to an online template, make thoughtful choices about how you'll architect your plans.

  • Part 1: Break down the variable choices in planning, and learn how to adjust them over time. Learn common pitfalls many teams make.

  • Part 2: Build the templates you'll use: objectives, architecture, schedule.


Module 3: Translate plans into action with an "Operating Cadence"

You need a system to ensure goals are hit, and your team is clear on what to do and when.

  • Part 1: Break down the variables teams consider when concocting their calendars and workflows.

  • Part 2: Use our template to build your Operating Cadence so you can lead with more intention and clarity.

Workshop schedule

2 weeks; 5 - 6 hours per week
  • Orientation and Social

    First Monday, 3 - 4pm PST

    Get an overview of materials and tools, and meet peers attending alongside you.

  • Live Sessions

    Tuesdays and Thursdays, 3 - 5pm PST

    This workshop has 4 central sessions, hosted live Tuesday and Thursday.

  • Optional Office Hours

    Wednesdays and Fridays, 10am and 3pm PST

    Scheduled after each live session, offered at 2 separate times. Bring your questions on the materials, or ask for help on your projects.

  • Pre-work and Projects Completed Offline

    1 - 2 hours per week

    Each live session has ~30 minutes of pre-work with materials to watch and read ahead of time.

    There are 3 projects you'll develop: In the 1st week, you'll complete the first and start the second. In the 2nd week, you'll complete the second and the third.

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Learning is better with cohorts

Learning is better with cohorts

Active learning, not passive watching

Learning from live sessions and hands-on projects

Interactive and project-based

You’ll be interacting with other learners through breakout rooms and project teams

Learn with a cohort of peers

Join a community who want to learn and grow alongside you

Frequently Asked Questions

Can I get my company to pay for this?
I work full-time. What's the time commitment?
What projects will I complete?
What happens if I can’t make a live session?
What’s the refund policy?
I have other questions.
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