Startupfest | From Founder to CEO Bootcamp

"The skills of the CEO determine the ceiling for a startup."

— Mike Lewis, General Partner

You have a product. You have customers. Maybe your first hire or two. Suddenly, your job shifts in two directions at once. The first shift is internal. You can’t do everything yourself anymore. The skills that got you here, intensity, hands-on control, knowing every detail, start working against you. You have to learn to work through people, not just alongside them. The second shift is external. At the early stage, you are the company’s voice. You have to learn to tell a story that makes investors write checks, customers buy, and great candidates want in. You have to learn to sell before you have a sales team. You have to learn to run a fundraising process before you’ve ever done one.

Most founders learn this out the hard way. Startupfest and Enjoy the Work are bringing early-stage founders together for a two-day bootcamp: practical frameworks on storytelling, founder-driven sales, fundraising, and early team-building, designed for founders who are ready to embrace the challenge of making the change from Founder to CEO.

Your startup is unique. Your problems are not.

Founders work with the team at Enjoy the work for one reason: better outcomes. Their General Partners have guided 250+ startups. They work with founders, helping them launch, grow, hire, win business, raise capital, and when the time is right, exit. Companies in their community include Tipalti, the fintech unicorn automating B2B payments globally; HoneyBook, the unicorn platform running the back office for independent service businesses; and Mudflap, the unicorn rewriting trucking's fuel economics. Not to mention the success stories from the Canada Startup Ecosystem such as Paper, the edtech unicorn, and RVezy, the peer-to-peer RV marketplace.

What to expect from the Bootcamp:

Attendees leave with practical frameworks across six focused sessions:

Day 1 — Story and Market

Win Every Day: A practical system for managing time, energy, and priorities. Founders learn to run their day instead of letting it run them.
Startup Storytelling: How to build a story that works across fundraising, sales, and recruiting. Includes a live demonstration of Enjoy The Work’s storytelling process.
Founder-Driven Sales: How to run early-stage sales conversations, qualify leads, and start building a repeatable sales motion before you have a sales team.

Day 2 — Raise and Build

Fundraising Is Much More Than a Pitch Deck: A framework for running a professional raise: the 28 questions all investors ask, what a minimum viable investor funnel looks like, and how to close with discipline.
Finding the Right Talent: How to build a pipeline, vet candidates, and close early hires when you’re small and every seat matters.
CEOs: How to Build Leverage: Goals, delegation, and feedback for early-stage leaders. How to shift from doing the work to helping others do their best work.

The Bootcamp is for you if...

You are:

Seed-stage / early-revenue founders
Venture-backed tech companies
CEOs making the jump from 'builder' to 'leader'
Founders with a small team (up to 10 people)
Ambitious, coachable, and short on time

Your goals are:

Scaling: You have a product and early customers, but need to build a repeatable company.
Fundraising: You have a raise on the horizon and need to sharpen your positioning before meeting investors.
Levelling up: You’re short on time and looking for high-leverage, practical tools rather than theory.

FAQ

Why do I have to apply?

The bootcamp is for founders who've moved past invention. You've shipped something, you have customers using it, and now you're staring at a different problem: how do you build a company around it? That's the work we do in the room. Founders still debating whether to run a company, or sitting on an idea they might someday pursue, won't get value here; and worse, they'll dilute it for everyone else. The application keeps the cohort tight. Everyone in it is doing the same job.

How will I know if my application is accepted?

We will respond to every application via email within 5 business days of receipt of the application with an approval, rejection or request for additional information.

I’m interested but would really like to talk to someone first before committing; is that possible?

Absolutely, we recognize that this is not a small decision. Please send us a note here referencing that you want to chat about the bootcamp. We’ll set up a call with you and one of our partners asap.

For the Bootcamp, when do I need to arrive in Montréal?

The intensive kicks off with an optional (but highly recommended) dinner for the cohort the evening of Sunday, July 5th. The curriculum begins first thing the next morning.

In what language will the bootcamp be conducted?

The bootcamp will be conducted entirely in English.

Ok, I want in. How do I secure my spot?

Once you’ve had your application accepted, we’ll send you a payment link to secure your place and a deadline for submission. Apply now.

From Founder to CEO Bootcamp

"The skills of the CEO determine the ceiling for a startup."

— Mike Lewis, General Partner

Your startup is unique. Your problems are not.

$13B+

$1,4B+

250+

11

Space is very limited

How to Attend:

What to expect from the Bootcamp:

The Bootcamp is for you if...

You are:

Your goals are:

What others had to say...

FAQ

Content Partner