CEO Bootcamp – Enjoy The Work

Raise Your Ceiling

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“The skills of the CEO determine the ceiling for a startup.”
– Mike Lewis, General Partner & Bootcamp Instructor

The Story

The founder journey is lonely and difficult. Everything seems to shift all the time and you’re expected to have all the answers. Worse still, you very job seems to be in constant flux. At first you’re the inventor,  spotting a need no one else sees. With creativity and grit you bring a first product to life.

But then, with effort and a bit of luck, customers start buying what you’ve built. That’s when everything about your job changes.

You go from inventor to leader. In other words, you begin the transition from founder to CEO.

Who We Are

Your startup is unique, your problems are not.

Our team of General Partners are accomplished former founders, operators, and investors who have guided more than 200 startups since 2015. 

  • We met Chen the co-founder/CEO at Tipalti when his business was <$10M in revenue. It’s last valuation? $8.3B.
  • We started working with Oz and his team at Honeybook following their Series A. Now, the business is valued at more than $2B.

We are fortunate to have been a part of similar stories for many high flying startups such as Mudflap, Darrow.ai, Paper Education, PeopleOne Health, Cactus, WorkHelix, Percepto and many others; not to mention those of our companies who already have exited. Great outcomes for our founder Gabe at The Wild (acquired by AutoDesk), San and KP at Enview (acquired by Matterport) and Matt and Naveen at Indus (acquired by Procore).

We’ve seen this movie before; we’re here to help our founders avoid the errors that have doomed so many others.

The Opportunity 

This Winter, we’re offering an Enjoy The Work Fully Remote CEO Bootcamp.

Fully Remote

Our fully remote bootcamp delivers interactive workshops, breakout sessions and hands-on coaching – to founders around the world. You’ll tune in alongside a global cohort, learn from the same expert instructors and follow the same immersive program designed to sharpen your CEO skills and surface the insights that fuel the Bay Area’s startup engine. By the end, you’ll walk away with new frameworks, a deep understanding of what makes great startups tick and a network of peers you can call on no matter where you’re based.

Eligibility

You are a leader, CEO, or founder of a startup that has team members that report to you.

You may have held a leadership seat before, but you’re facing new challenges.

You are convinced your company could move faster, more effectively.

You are hungry to learn and grow as a startup CEO.

You know the difference between building your company and building yourself. We’re here for founders serious about leveling up as CEOs.

Apply for the CEO Bootcamp

Some Of What You’ll Learn

If you’ve raised some money, have a product in market, and are trying to go from “founder who does everything” to “CEO who builds something enduring,” this is for you.

You’ll walk away with:

  • The core systems great CEOs use to run, plan, and prioritize
  • Clarity on how to delegate, give feedback, and set direction
  • Tools to make hiring decisions, run effective sprints, and prep your board
  • A clearer path to becoming the leader your company actually needs

Nothing academic here; only frameworks and templates that can be put to work immediately to improve life at your startup. Included within the curriculum:

  • Enjoy The Work’s ​​Fundraising Playbook: Learn how the best founders raise capital; we’ve guided 350+ raises totaling $1.4B
  • Win Every Day: Enhance your own practices to be more efficient and effective
  • Ensure PMF Is Accomplished: Learn what simple, effective user research means and how to measure and gauge PMF
  • Hiring A-Players: Internalize how to consistently make superior talent decisions
  • Velocity and Accountability: The best team moves quickly and reliably; learn how to instill a culture of speed
  • Management and Delegation: Master running great meetings and how to hand projects off to others effectively
  • High Leverage Decisions: Learn how the best CEOs decide what to work on and when

Global Program / Virtual

Dates: December 2-3, 2025
Registration Deadline: November 28
Pricing: $999

  • Workshops, breakout sessions, and curated content all designed to catalyze your CEO skills
  • Access to immediately applicable playbooks and templates to implement at your startups
  • A network of similar stage founders for networking, introductions and references

Apply for the CEO Bootcamp

Our teachings have led to unicorns and exits – now it’s your turn

Enjoy The Work General Partners study how the best startups in the world operate. The program curriculum will be supported by an exclusive collection of videos, frameworks, samples and templates. These are the same skills we’ve taught the teams of many of our wildly successful startups from over the last 10+ years including:

  • HoneyBook

    Unicorn

    HoneyBook helps businesses manage projects, clients, and money.

  • Tipalti

    Unicorn

    Tipalti is the most efficient payables automation system on the market.

  • Paper

    Unicorn

    Give every student an equal opportunity to excel, with Paper.

  • Enview

    Exit

    Enview is a top trusted 3D geospatial analytics company.

  • Headnote

    Exit

    Law firms get paid faster with Headnote.

  • The Wild

    Exit

    The Wild streamlines every AEC workflow.

  • Addy

    Exit

    Addy empowers small businesses to be great marketers.

  • EnjoyHQ

    Exit

    UX teams use EnjoyHQ to learn from users faster.

  • Indus.ai

    Exit

    Indus uses AI to streamline construction sites.

  • Sparrow Connected

    Exit

    Sparrow brings your workforce together with omnichannel communications.


Want to learn more about what we teach before applying?

The best way to get a feel for Enjoy The Work is to hear it straight from the #1 technology podcast in the US – Lenny’s Podcast. Listen to when Lenny himself interviews our founder Jonathan on how Enjoy The Work coaches, challenges, and champions startup CEOs.

Watch or listen to the full episode below:

Apply for the CEO Bootcamp