Enjoy The Workshops – Enjoy The Work

Enjoy The Workshops

Pick the talks your team needs next.

A menu of workshops we deliver to startups and operators — grouped by what your organization is trying to solve right now.

Section

Raising Capital

Founders & Investors — Who Is Making The Bigger Bet?

This interactive workshop unpacks the high-stakes dynamics between founders and investors, from capital and control to risk and return. Learn how to balance competing incentives, align expectations, and build partnerships that drive sustainable growth.

This interactive workshop unpacks the high-stakes dynamics between founders and investors, from capital and control to risk and return. Learn how to balance competing incentives, align expectations, and build partnerships that drive sustainable growth.

01

Early Stage Fundraising — Fundraising Is Much More Than a Pitch Deck

This talk covers revealing topics such as “The 28 Questions All Investors Ask” and what represents a “Minimum Viable Investor Funnel,” providing the audience with frameworks from which to construct a professional fundraise regardless if your startup is barely off the ground or well beyond product-market fit.

This talk covers revealing topics such as “The 28 Questions All Investors Ask” and what represents a “Minimum Viable Investor Funnel,” providing the audience with frameworks from which to construct a professional fundraise regardless if your startup is barely off the ground or well beyond product-market fit.

02

Late Stage Fundraising — Time to Think Like a Banker

This talk dives more deeply into what sets later stage raises apart and covers the new objections you’re likely to face, the difference between repeatable and scalable, the criticality of the curated data room, and the central importance of your financial plan.

This talk dives more deeply into what sets later stage raises apart and covers the new objections you’re likely to face, the difference between repeatable and scalable, the criticality of the curated data room, and the central importance of your financial plan.

03

How To Raise An Inside Round

Few startups grow steadily without hiccups. When they hit bumps, raising capital from familiar investors often makes sense. Inside rounds differ from outside ones in key ways. This talk will explain how.

Few startups grow steadily without hiccups. When they hit bumps, raising capital from familiar investors often makes sense. Inside rounds differ from outside ones in key ways. This talk will explain how.

04

Building A Financial Plan You’ll Actually Use

Planning is a skill that connects the assumptions you have about your business with the financial outcomes you desire, with the operational initiatives required to achieve those outcomes. Most startups are terrible at this. Learn how the best are able to predict the future.

Planning is a skill that connects the assumptions you have about your business with the financial outcomes you desire, with the operational initiatives required to achieve those outcomes. Most startups are terrible at this. Learn how the best are able to predict the future.

05

How To Entice The Acquisition You Want

The best exits often are not a surprise; they are long in the planning. Disappointing exits occur when the founder hangs a for-sale sign up for all to see. Learn how you can orchestrate the former and avoid the latter.

The best exits often are not a surprise; they are long in the planning. Disappointing exits occur when the founder hangs a for-sale sign up for all to see. Learn how you can orchestrate the former and avoid the latter.

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Section

Go To Market

Startup Storytelling — How To Build Your Story

Telling a great story isn’t magic; it’s a crucial skill anyone can learn. Learn the key elements and witness a live demonstration of Enjoy The Work’s process. Gain a competitive edge in fundraising, recruiting, managing, or selling.

Telling a great story isn’t magic; it’s a crucial skill anyone can learn. Learn the key elements and witness a live demonstration of Enjoy The Work’s process. Gain a competitive edge in fundraising, recruiting, managing, or selling.

01

Founder Driven Sales — How The Best Founders Win Deals

This workshop helps founders land their first deals and turn sales into product insights by mastering outreach, lead qualification, demos, proposals, and negotiation, creating a repeatable framework that builds trust, boosts revenue, and drives sustainable growth.

This workshop helps founders land their first deals and turn sales into product insights by mastering outreach, lead qualification, demos, proposals, and negotiation, creating a repeatable framework that builds trust, boosts revenue, and drives sustainable growth.

02

Unpacking Product Market Fit

Early-stage founders know the term but may disagree on its meaning, how to reach it, or what to do when it’s elusive. This talk shows clear customer-acquisition signals to confirm you’re on the right track.

Early-stage founders know the term but may disagree on its meaning, how to reach it, or what to do when it’s elusive. This talk shows clear customer-acquisition signals to confirm you’re on the right track.

03

Positioning Your Startup — Finding Your Uncommon Denominator

Learn how to create clear, honest positioning that helps customers quickly understand what you do, who it is for, and why you are a better fit than the alternatives.

Learn how to create clear, honest positioning that helps customers quickly understand what you do, who it is for, and why you are a better fit than the alternatives.

04

A Framework For Complex Sales

Sometimes a single deal can redefine a startup’s trajectory. From partnerships to lighthouse customers to acquisitions, these pivotal moments are game-changers. Learn how seasoned veterans approach complex selling via Enjoy The Work’s 2×4 framework.

Sometimes a single deal can redefine a startup’s trajectory. From partnerships to lighthouse customers to acquisitions, these pivotal moments are game-changers. Learn how seasoned veterans approach complex selling via Enjoy The Work’s 2×4 framework.

05

Growing Beyond Founder Driven Sales — Building Your Go To Market Machine

This hands-on workshop will show you how to build the systems your startup needs to scale, from defining your ideal customer to creating a winning sales playbook. Unlock the tools to transform your business from scrappy to sustainable, and get ready to reach escape velocity.

This hands-on workshop will show you how to build the systems your startup needs to scale, from defining your ideal customer to creating a winning sales playbook. Unlock the tools to transform your business from scrappy to sustainable, and get ready to reach escape velocity.

06

So You’re Thinking About a Pivot… A Guide to the Word We All Fear, But We All Need

One of the most misunderstood words in the entrepreneur’s dictionary is “pivot.” When a founder discovers product market fit, it is not subtle. It’s overwhelming. Knowing when and how to pivot can make all the difference. In this one-hour fast-paced workshop, we share when a pivot should be considered, and the various types of pivots founders might consider.

One of the most misunderstood words in the entrepreneur’s dictionary is “pivot.” When a founder discovers product market fit, it is not subtle. It’s overwhelming. Knowing when and how to pivot can make all the difference. In this one-hour fast-paced workshop, we share when a pivot should be considered, and the various types of pivots founders might consider.

07

Architecting Your Sales Playbook

This hands-on workshop will show you how to build a practical sales playbook, from defining your ideal customer and qualifying leads to running outreach, demos, proposals, and negotiation with consistency.

This hands-on workshop will show you how to build a practical sales playbook, from defining your ideal customer and qualifying leads to running outreach, demos, proposals, and negotiation with consistency.

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Section

Management

What Makes A Great Startup CEO

Ask investors to describe what makes a great founder, and the answers will be remarkably consistent. Ask that same audience what makes a great CEO and the answers wildly shift from attributes to skills. But what are those skills and in what sequence should founders seek to acquire them? This talk explores the journey from founder to CEO.

Ask investors to describe what makes a great founder, and the answers will be remarkably consistent. Ask that same audience what makes a great CEO and the answers wildly shift from attributes to skills. But what are those skills and in what sequence should founders seek to acquire them? This talk explores the journey from founder to CEO.

01

The Seven Deadly Sins of Startup Management

This session closes the gap between steady CEO attributes and shifting views on skills by naming the core abilities founders need, strategic vision, team leadership, financial acumen and execution, and laying out the best order to master them. You’ll leave with a clear roadmap, complete with milestones and tools, to guide your journey from founder to CEO.

This session closes the gap between steady CEO attributes and shifting views on skills by naming the core abilities founders need, strategic vision, team leadership, financial acumen and execution, and laying out the best order to master them. You’ll leave with a clear roadmap, complete with milestones and tools, to guide your journey from founder to CEO.

02

Win Every Day

A practical system to help founders manage time, set priorities, and execute with consistency.

A practical system to help founders manage time, set priorities, and execute with consistency.

03

Introduction to Leverage: Goal Setting

Goals are the operating system of your company. Done right, they are not corporate theater or busywork, but the most direct way to get everyone moving toward the same outcome. In this session, we will show you how to set goals that move fast, focus energy, and build shared purpose. Teach the rapid goal-setting framework.

Goals are the operating system of your company. Done right, they are not corporate theater or busywork, but the most direct way to get everyone moving toward the same outcome. In this session, we will show you how to set goals that move fast, focus energy, and build shared purpose. Teach the rapid goal-setting framework.

04

You Are the Bottleneck — How The Best CEOs Delegate

Being a great founder and being a great manager are not the same thing. As your team grows, your job shifts from doing the work to helping others do their best work. This session is about the everyday skills that make that possible: how to delegate and build a team that runs well even when you’re not watching.

Being a great founder and being a great manager are not the same thing. As your team grows, your job shifts from doing the work to helping others do their best work. This session is about the everyday skills that make that possible: how to delegate and build a team that runs well even when you’re not watching.

05

CEOs — Learn How To Deliver Feedback

Effective feedback is a founder’s key leverage. Master the skill, and you can elevate your team; don’t learn it, and watch your best talent head for the door. It’s not magic; it’s a learnable skill for any curious leader wanting to become a better manager.

Effective feedback is a founder’s key leverage. Master the skill, and you can elevate your team; don’t learn it, and watch your best talent head for the door. It’s not magic; it’s a learnable skill for any curious leader wanting to become a better manager.

06

The Pursuit of Management Leverage

Some people make your work easier. Others make you wonder if you should have just done it yourself. This workshop helps leaders create more positive leverage across their teams by improving how they give direction, set expectations, and support execution.

Some people make your work easier. Others make you wonder if you should have just done it yourself. This workshop helps leaders create more positive leverage across their teams by improving how they give direction, set expectations, and support execution.

07

High Performing Cultures: How To Build One & How To Keep One

If your brand identity is the promise you make to your customers, your culture is the promise you make to your employees. Keep your promises, and your business can thrive. Break them, and peril awaits.

If your brand identity is the promise you make to your customers, your culture is the promise you make to your employees. Keep your promises, and your business can thrive. Break them, and peril awaits.

08

Finding The Right Talent — Hiring A-Players

It all starts with the team. Recruit the right early folks, and you’ll have the fuel you need. Miss too many times, and you might fall before even getting started. In this talk, learn how to build a pipeline, vet a candidate, close the best, and ramp up new team members.

It all starts with the team. Recruit the right early folks, and you’ll have the fuel you need. Miss too many times, and you might fall before even getting started. In this talk, learn how to build a pipeline, vet a candidate, close the best, and ramp up new team members.

09

Startup Comms Architecture

Alignment is easy in small teams. As companies grow, communication gets harder. This talk explains what communication architecture is, why it matters, and how to put it in place.

Alignment is easy in small teams. As companies grow, communication gets harder. This talk explains what communication architecture is, why it matters, and how to put it in place.

10

How To Cultivate A Thriving Boardroom

In some boardrooms, the directors are knowledgeable, thoughtful, and candid. In others, politics reign. But it doesn’t have to be left to chance. In this talk, we’ll cover what great looks like, and the set of steps required to get there.

In some boardrooms, the directors are knowledgeable, thoughtful, and candid. In others, politics reign. But it doesn’t have to be left to chance. In this talk, we’ll cover what great looks like, and the set of steps required to get there.

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