Natalie Hoop

Why Fractional Leadership Is the Smartest Move No One Talks

Fractional Ops Partner  | +238% Sales, +68 Margin Points | Coach

Spot the signs you're burning cash, stalling growth, or hiring too early and what to do instead.

When to hire a fractional leader

See how operators increase revenue, fix delivery, and unlock margin without full-time overhead.

What fractionals really deliver

Learn why most fractional partnerships fail and how to build one that actually works.

The mistakes that ruin results

Your job as CEO isn't to be the best employee in your company. It's to build the machine that runs without you. But here's what most CEOs get wrong: they think scaling means hiring more people. The smartest CEOs in 2025 are building AI-first companies that generate more revenue with fewer humans. I should know - I've done it three times. At Joany, my health insurance startup, we had 26 employees. But 5 of them weren't human - they were AI agents handling invoice reconciliation, collections, state filing, and customer service. The result? 96% profit margins while our competitors struggled with 20-30% margins and bloated teams. That was 10 years ago before AI was cool. Today, building an AI-first business is 10x easier. What took me custom engineering teams to build can now be deployed over a weekend. But here's the foundational problem most CEOs miss: If you can't delegate to humans effectively, you'll never leverage AI. The same mindset blocks that keep you trapped doing $25/hour work will sabotage every AI agent you try to deploy. This isn't about adding AI to your existing chaos. It's about rebuilding your operating system from the ground up. In this intensive, you'll learn: - Why you can't scale (with humans OR AI) until you fix your delegation foundation - The exact system I use to run multiple 8-figure businesses working ~20 hours/week - How to design AI-first workflows that multiply your capacity without multiplying your management overhead The opportunity window is closing fast. AI-first companies are pulling ahead. Join them before it's too late.

Build an AI-First Business Machine That Scales Without You

Course syllabus

(this isn't theory - you need real operations to transform)

❌ You don't currently run a business generating at least $500K in annual revenue

❌ You want to stay hands-on forever vs building systems 

❌ You're looking for passive income "hacks" or shortcuts

❌ You believe AI will replace all human creativity

❌ You prefer hiring people over building systems

❌ You think "good enough" processes are fine

❌ You don't want to challenge your current methods

❌ You need constant hand-holding to implement

This course demands you think like an AI-first CEO, not a traditional manager.

⚠️ This Intensive Isn't For Everyone

You should NOT take this course if:

You're a CEO or founder who wants to run and grow your business with less effort.

You execute like a beast, but know that to scale your business, you need to learn to scale yourself.

You want to run your business, but lately it feels like it's running you.

Who is this course for

Master the AI-First CEO frameworks to scale yourself and your business

Learn how to work with AI agents and human assistants to create exponential leverage. Master the art of AI-first delegation that multiplies your capacity without multiplying your management overhead.

Deploy Your AI Workforce (Starting with an Executive AI Assistant)

Develop frameworks to automate workflows before you hire for them. Design AI-first processes that scale from startup to $200M+ without breaking.

Build systems that run your business without you

Use proven delegation and AI automation frameworks to eliminate yourself from 80% of daily operations. Protect your mental capacity for the strategic work only you can do.

Reclaim 20+ hours per week (while growing faster)

Identify the highest-leverage CEO activities and design systems for everything else. Build the predictable, scalable machine that grows without you.

Ruthlessly Focus On The 10% That Matters (While AI Handles the 90%)

Deploy the CEO Decision Architecture that removes emotional burden and analysis paralysis. Make confident decisions with incomplete information while your systems handle the execution.

Make faster, higher-quality decisions

I Built a $200M Company with AI 'Employees' Before AI Was Cool. Here's the framework that made it possible.

Christine Carrillo

Entrepreneur, CEO Coach

Cohort 15: July 2025

Cohort 16: October 2025

Is the thought of going out on your own both exhilarating and terrifying? I’ve been exactly where you are. You’re a seasoned operator. You’ve built teams, led complex projects, and climbed the corporate adder. But turning that experience into a business of your own? That's uncharted territory. If you’re like most new fractionals, you’ve probably been spinning your wheels: tinkering with your website, sending cold emails with no replies, second-guessing your pricing, or wondering if you’re “doing it right.” The questions feel endless: → How do I turn my expertise into an offer people actually want?→ How do I find and land my first clients?→ How (and what) do I charge?→ How do I set up the back-office of my business? I’ve been there. And after 3+ years, 30+ clients, and nearly doubling my 9-5 salary through fractional, consulting, and advisory work, I designed this course to give you the exact playbooks, tools, and guidance I wish I had when I started. What You'll LearnIn this 3-week sprint, we’ll turn your expertise into a compelling offer, price it with confidence, and fast-track your path to launching your business and finding your first clients. You’ll walk away with:👉 A vetted one-pager that clarifies your positioning and unique value you bring to clients👉 Proven sales and relationship-building frameworks to build your initial pipeline of opportunities👉 A step-by-step launch playbook—with easy-to-apply templates—to take your practice from 0 to 1👉 Light-weight systems and tools to set your business up for success👉 Confidence and clarity—through hands-on workshops, coaching, and community—to actually start this next step in your career Course FrameworkThis course is packed with:👉 4 Live Workshops👉 2 Group and 1:1 Office Hours Opportunities👉 2 Projects for Feedback👉 Async Feedback &amp; Peer Support👉 A Notion Toolkit with Plug-and-Play Tools &amp; Templates👉 Access to a Fractional Alum Slack Community Why Learn From Me?I've spent the past decade working inside high-growth consumer startups like Rent the Runway, The Wing, and Tia. Three years ago, I left that world behind and launched my fractional practice, Next Wave Marketing. Since then, I’ve worked with 30 mission-driven clients, built a 6-figure business, and—most importantly—designed a career that fits into my life, not the other way around. Whether you’re ready to go all-in on fractional work, easing your way into it, or just looking to diversify your income outside of your 9-5, I'm here to help you kickstart your journey with confidence.&nbsp;I hope you'll learn with me!

It’s time to get off the sidelines and launch your fractional practice.

We'll come together for live, interactive workshops on Monday and Wednesday afternoons.

3x Live Sessions – Monday & Wednesday

Have a question or want to workshop progress? Join office hours to get hands-on, actionable feedback from me and your peers.

2x Office Hours

Throughout the course, access bonus materials, pre-work, projects, and templates that you can directly apply to your business.

Async – Pre-Work, Post-Work & Templates

Course schedule

Full-Time Operators Looking For Greater Freedom + ImpactLearn how to monetize your expertise and diversify your income outside of your 9-5.

Senior Leaders (8+ Years of Experience) in TransitionAssess whether or not fractional work is the right path for your career journey.

New (&lt;6 mo) to Fractional WorkStandup your practice with confidence, clarity, and proven playbooks and accelerate the learning curve.

Who this course is for

You'll leave this course with:

Walk away with a focused, ownable way to describe what you do, who you help, and the unique value you bring.<ul><li>Define your initial offerings</li><li>Create your initial one-pager to use in outreach and discovery calls</li><li>Get personalized feedback from me and your peers</li></ul>

A clear positioning statement and offer suite that reflects your strengths

Learn proven, relationship-driven sales strategies to activate your network and attract your first clients—without feeling salesy.<ul><li>Apply proven, relationship-driven outreach strategies</li><li>Set up your lightweight CRM</li><li>Start building a pipeline of warm leads and referrals</li></ul>

Tactical networking & sales strategies to build your early pipeline and land your first projects

Take the guesswork out of pricing and scoping so you feel confident putting together proposals that close.<ul><li>Understand pricing models (hourly, retainer, project-based)</li><li>Define your pricing and offer strategy</li><li>Learn how to structure scopes that protect your time and value</li></ul>

Proven techniques to scope, price & set up client engagements for success

Leave with a step-by-step action plan and templates to launch your fractional practice, whether you're taking the leaping now or easing into it over time, including:<ul><li>Outreach Templates</li><li>Discovery Call Scripts</li><li>Scope &amp; Contract Templates</li><li>Systems Starter Kit</li></ul>

Templates, tools, systems, and a clear action plan to go from 0 to 1

You don't have to figure this out alone. Accelerate your transition with confidence with through:<ul><li>Personalized feedback on your positioning statement &amp; sales plan</li><li>Weekly office hours for 1:1 support</li><li>Collaboration and connections with operators navigating similar challenges</li></ul>

Personalized feedback and peer support from other operators navigating this transition

Learn how to confidently launch and grow a fulfilling independent consulting, advisory, or fractional practice.

Emily Hollender

Fractional Operator | Startup Advisor

Cohort 1

Cohort 2

The ChallengeYour days are filled with:🗓️ back-to-back meetings,🚀 sky-high customer or investor expectations,⏱️ wishes that your team could move faster sooner,🔥 wishes that you could move even faster and work on what really matters instead of fighting fires. You start each day with the best intentions, but somehow find yourself constantly reacting instead of leading.&nbsp;Sure, it would be nice to focus on your own goals, but you care about those other people (or at least some of them 😁). They’re colleagues and customers, family and friends... How can you collaborate with them responsively without forsaking your goals and becoming just a (re-)Actor in their story? 🎬 ✨ You wonder if AI can help, you wonder how other leaders are using AI to manage it all and manage their teams--but honestly, who's got the time to figure that out? ⏳ You have a constant, lurking anxiety about what’s falling through the cracks or not getting done, so you work faster. As you try to move faster, people fall short of your expectations and their potential. It causes friction and frustration (even if you hide it well). It's uncomfortable to call out, so you avoid giving feedback or mention it lightly, which makes the situation more uncomfortable. Eventually, you decide to give feedback. Sometimes it goes okay. Often, you try to move through and out of the conversation as quickly as possible because it feels so awkward. Growth and improvements rarely last. You take on more work yourself to get it done. The Solution (Evidence-based. Immediately applicable.)⏱️&nbsp;EVERYTHING YOU READ BELOW WILL BE ORIENTED TO IMMEDIATE APPLICATION DURING THE COURSE ⏱️What if you could shift from reacting to the constant inputs to creating what matters most and leading your team in that direction--everyday? This course will support you, step by step, in building your Operating System to make this shift. Fancy apps aren't enough. Nor are bursts of motivation. A sustainable Operating System has 3 features:🧰 Tools (simple enough to keep using, and amplified by AI)🔁&nbsp;Habits (the tools don't use themselves...except for some of the AI ones we'll build)🧠 Mindsets (you can "productively" spend your life responding to other people's messages and requests--or build something that matters) No, "perfection" isn't possible (or even desirable). But our days--and our results--completely shift when we focus our attention systematically instead of ad-hoc and reactively. And our conversations shift when we stop trying to fix people and start inspiring them to take action and grow. We teach you how to do this by using straightforward approaches that reliably transform defensiveness and friction into self-reflection, connection, and motivation to grow. You will start to look forward to feedback conversations because you will know how to use them as powerful tools for building trust and deepening connection. You will also explore your own mindsets and beliefs around feedback, identifying your own patterns around conflict avoidance, people-pleasing, and controlling behaviors. AI is woven throughout the course, including:1️⃣ building your own Custom GPTs2️⃣&nbsp;mastering your calendar3️⃣ using AI as a practice partner for difficult conversations and coaching skills4️⃣ helping your team use AI, and so much more! Once you've shifted the way you manage yourself and lead your team conversations, applying evidence-based approaches tested with 1000s of managers and amplified with AI, the whole game becomes fun again. Bonus:📝 You will also get 5 step-by-step facilitation guides for sharing and teaching your team members everything we cover in this course. This helps establish shared language and frameworks within your team/organization, and positions you as the leader of change. 📖&nbsp;You'll also get our 20-page Offsite Playbook with step-by-step guidance on how to design and facilitate unforgettable team and company gatherings. 🚀 And you'll get to do this while in a practice lab with other high-growth leaders.

Spend your days fighting fires or each other?

Tuesdays (+ 1 Thursday)

Weekly Office Hours

High-Growth ManagersReady to move out of IC mode, you want to be the inspiring leader people thank for the rest of their careers.

ExecutivesYou know there's a better way than back-to-back meetings everyday. To scale your impact, you know you must scale yourself first

Startup FoundersYou're expanding your focus from building a product to building a team. And to do so, you need the team to step up fast.

What you’ll get out of this course

You'll have the Inner and Outer Game in place:<ul><li>A systematic set of habits, tools, and mindsets to define What Matters Most each day and week</li><li>You'll be using your emotions as signals for what needs to happen next</li><li>Your mind will be at ease</li></ul>

Clear Focus & Emotional Balance

Whether you're currently intimidated by AI, curious, or all-in, you will:<ul><li>know exactly how to leverage Claude and ChatGPT to improve your skills and help you prepare for key conversations</li><li>have your own CustomGPT to do a recurring management task FOR you</li></ul>

AI As Your Ally (including your own CustomGPT)

<ul><li>Next Actions template (simplest tool possible to stay organized)</li><li>Weekly Preview Checklist (define what matters most and who should do it)</li><li>Daily Defining Checklist</li></ul>

The Operating System (feel on top of your s***)

<ul><li>Know how to decide WHAT to delegate to increase your leverage</li><li>Know HOW to delegate (to a person or AI) in ways that build confidence and follow-through</li></ul>

The Leverage Framework

<ul><li>GAIN Template for how to structure feedback conversations that inspire response-ability, action, and growth</li><li>how to use AI to prepare and practice</li></ul>

GAIN Feedback Framework

<ul><li>GROW Template for coaching conversations</li><li>The key skill to coach effectively</li><li>Know the difference between a feedback and a coaching conversation</li><li>how to use AI to practice and get feedback on a coaching conversation</li></ul>

GROW Coaching Framework

What if you felt on top of everything?
What if your team were aligning and growing through every conversation with you?

Jack Cohen

Overall, leadership in remote workplaces requires a shift in mindset and a different set of skills compared to traditional office-based leadership. This course will help you develop the skills necessary to be a remarkable leader in virtual and hybrid work places. You will enhance your ability to communicate, create trust, adapt, and how to leverage technology to create a productive and connected virtual work environment.

Empower yourself and your employees to thrive in virtual and hybrid environment

We will meet for two hours as a group on Zoom (link in the calendar invite)

February 8th and February 15th

At the end of our first session you will have an assignment to complete prior to our second program.

Weekly projects

You are a people leader looking to maximize productivity in a remote and hybrid working environment.

You want to help foster collaboration and team cohesion despite physical distance.

You care about the wellbeing and mental health of your employees and want to create an environment of psychological safety.

What you can expect from this course

You will learn to sharpen the communication of yourself and your team by becoming more concise, inclusive, and proactive to ensure everyone on your team is on the same page and connected.

Enhance your communication skills

You will learn how to implement strategies to improve regular team meetings, inclusive decision-making processes, enhance psychological safety, and virtual team-building activities to create a deeper a sense of unity.

Enhance the dynamics of your team

You will work through common and challenging scenarios that occur in hybrid and virtual environments. These exercises will give you a plan of action to handle situations in your own working environment.

Hands-on practice and application

During our program you will receive materials and resources that can be used on an ongoing basis after our sessions end (such as team exercises, virtual project retrospective templates, etc.).

Resources and tools

This course will teach you to excel as a leader in a hybrid and virtual workplace.

Lightning Lessons

Why Fractional Leadership Is the Smartest Move No One Talks