CMO School

What does it actually look like to support a high-level founder as a Fractional CMO or strategic marketing partner?

In this episode, I’m joined by my client Lori Harder, founder of Glōci, host of the podcast Earn Your Happy, and founder of multiple 7-figure brands - for a candid conversation about what high-growth founders need from their marketing leadership.

We’re breaking down what made Lori decide to bring in strategic marketing support, how to build trust (and what breaks it), and what marketers need to understand if they want to work with founders like Lori.

What we covered:

• How Lori and Chris have structured their marketing team across multiple brands
• What Lori found most valuable when it comes to working with a Fractional CMO
• How to build trust with visionary founders (and what quickie breaks it)
• What we did to launch her new mastermind recently
• What Lori’s learned from the best (and worst) hires she’s made

Whether you're currently working with personal brands or want to step into higher-level strategic roles, this episode will give you a peek behind the scense of what it really looks like.

Ready to take the next step?

If you’re ready to step into the Fractional CMO role but want support as you do it, Fractional CMO School is a 6-month coaching program + community to help you confidently lead, land high-ticket clients, and build the business you want.

🎓 Learn More → https://www.thecmooffice.com/fractional-cmo-school

TIMESTAMPS:

00:00 Meet Lori Harder: Building Brands, Businesses & Teams

01:45 How Lori Reinvented Herself Again and Again

03:00 The Superpower Behind Every Business She’s Built

05:10 Why Being Human Is Your Best Personal Brand Strategy

06:10 Behind the Scenes of Lori’s Marketing Team

07:15 Why Lori Chose to Keep Her Team Small

09:15 The Growth Opportunity They Almost Missed

10:00 Build the Business Around the Life You Want

12:00 Why Fractional Leadership Changes the Game

14:15 Why Lori Hired a Fractional CMO

15:15 When It’s Time to Bring in CMO-Level Support

16:00 The Advantage Fractional CMOs Bring to Clients

18:00 How to Build Trust With a New Client

20:45 The Scope Mistake That Breaks Client Trust

22:00 What a Fractional CMO Should—and Shouldn’t—Do

24:30 How Great CMOs Lead the Client Relationship

25:00 When Should You Push Back on a CEO?

26:00 How Visionary Founders Actually Want Feedback

28:00 Work With the CEO, Not Under Them

29:20 Ask More Questions Before Giving Advice

31:00 What Lori Wishes Would Change About Marketing

33:45 What’s Actually Working in Marketing Right Now

34:15 How Lori Uses AI to Create Better Content

35:30 Train AI to Become Your Creative Partner

36:45 The Next Level of Using ChatGPT

37:45 Where to Connect With Lori Harder

38:15 Build Your Fractional CMO Business Faster

You don’t need to know everything to be ready for the Fractional CMO role, but you do need to shift how you see yourself and show up.

In this episode, we’re unpacking the real reason so many experienced marketers hesitate to claim the title of Fractional CMO — and it’s not a lack of skills. It’s the belief that they have to be someone else first: more data-driven, more strategic, more “official.”

Here’s what we get into:

• What being “ready” actually looks like
• How to lead confidently, regardless of your background or experience level
• The 3 core traits that matter most in the Fractional CMO role
• What to do when imposter syndrome kicks in
• How to identify your blind spots (and fill them without trying to “fix” yourself)
• The shift from task-doer to strategic partner, and how to start making it today

If you’ve been waiting for someone to tell you you’re ready, this episode is the permission you’ve been looking for.

Ready to take the next step?

If you’re ready to step into the role but want support as you do it, Fractional CMO School is a 6-month coaching program + community to help you confidently lead, land high-ticket clients, and build the business you want.

🎓 Join the waitlist → Fractional CMO School

TIMESTAMPS:

00:00 “Am I Actually Ready to Be a Fractional CMO?”

01:35 Why Experienced Marketers Still Feel Unqualified

02:25 There’s No “Right” Background for a Fractional CMO

03:30 Your Blind Spots Don’t Disqualify You

04:30 Great CMOs Don’t Know Everything

05:45 Build a Team That’s Smarter Than You

07:15 The 3 Skills Every Great Fractional CMO Needs

07:30 #1: Ask Better Questions

08:25 #2: Think Like a Business Owner

09:30 Prioritize What Actually Moves the Needle

10:25 #3: Show Up as a Peer, Not a Task-Doer

11:15 Don’t Be Afraid to Push Back on Clients

12:15 You’re Probably More Ready Than You Think

13:00 Stop Waiting to Feel Qualified

13:50 Imposter Syndrome Can Be a Good Sign

14:15 Build Your Fractional CMO Business Faster

If you’ve ever held yourself back from posting, pitching, or showing up because you were afraid of being judged, rejected, or just not “ready” - this episode is going to shift something for you.

In this conversation, I’m joined by Maureen Evelyn - content strategist, personal brand coach, and the founder of Maureen’s Marketing. Maureen helps bold entrepreneurs turn their content into clients by building visibility, authority, and trust at scale. She’s known for creating over 100 pieces of content a month (without burning out) - and for helping her clients do the same.

We’ll talk about:

• What it really looks like to go from freelancer to leader
• The mindset that’s helped Maureen - and her clients - stop hiding and start growing
• How to build a personal brand that sells (without feeling salesy)
• Why she built Rejecto, an app that helps people get more comfortable hearing “no”
• And the messy, powerful process of stepping into your next-level self - even if it feels scary

Whether you’re a marketer guiding clients through visibility blocks, or a creative who knows you’re meant for more but haven’t fully claimed it yet - this one’s for you.

Ready to take the next step?

If you’re ready to step into the Fractional CMO role but want support as you do it, Fractional CMO School is a 6-month coaching program + community to help you confidently lead, land high-ticket clients, and build the business you want.

🎓 Learn More → Fractional CMO School — The CMO Office

TIMESTAMPS:

00:00 Meet Maureen: Building a Business at 21

00:45 How Rejection Changed Her Life

02:35 Stop Learning & Start Taking Action

04:45 Get Comfortable Being Uncomfortable

05:55 How Rejection Makes Business Easier

07:05 Turning Rejection Therapy Into an App

08:20 Rejection Happens at Every Level of Success

09:15 What If You Were Only 20 Rejections Away?

10:55 Why 300 Views Is Still a Win

11:55 How She Posts 100+ Pieces of Content a Month

13:15 The Simple Content Repurposing System

14:30 Stop Overcomplicating Your Content

16:30 Simple Content Can Still Get Huge Results

17:30 What to Post When You Have No Ideas

19:35 Consistency Makes Content Easier

20:50 The Secret to Creating Content That Stands Out

21:05 Double Down on What’s Weird About You

23:30 Stop Creating the Same Content as Everyone Else

24:20 You Can’t Think Your Way Into Great Content

25:35 Let the Algorithm Tell You What’s Working

26:20 The “Bad” Video That Got 20 Million Views

27:25 Content Advice for Fractional CMOs

27:45 Become the Person Your Ideal Client Wants to Be

29:35 Show Your Clients You Can Get the Result

Evergreen funnels sound like the dream - automated leads, passive income, a marketing system that runs in the background. But for most businesses, funnels don’t work the way they expect.

So, what separates a funnel that actually converts from one that just burns time and money?

In today’s episode, I sit down with Cheyenne Buttrey, founder of Copygirl.co, to break down what marketers need to know before investing in a funnel.

We’re covering:

• Who should (and shouldn’t) be using evergreen funnels
• What most marketers get wrong about funnel strategy
• The biggest mistakes that kill funnel performance before they even launch
• What elements make a funnel actually work—and what data marketers should be tracking

If you’ve ever wondered when and how to implement a funnel, this episode will give you the clarity you need.

Ready to take the next step?

If you’re ready to step into the Fractional CMO role but want support as you do it, Fractional CMO School is a 6-month coaching program + community to help you confidently land high-ticket clients and build a 6-figure (and beyond) business as a Fractional CMO.

🎓 Learn More → http://www.fractional-cmo-school.com/

TIMESTAMPS:

00:00 Why Most Marketing Funnels Don’t Work

01:00 Meet Cheyenne Buttrey: Funnel Strategist & Copywriter

02:20 Does Your Business Actually Need a Funnel?

03:35 The Core Elements of an Evergreen Funnel

04:25 How Long Does It Take a Funnel to Work?

06:55 Funnel Data Doesn’t Have to Be Complicated

07:25 The 3 Funnel Metrics You Need to Track

09:25 How to Diagnose a Funnel That Isn’t Converting

11:45 Don’t Scrap Your Funnel—Fix the Leaks

12:10 Why Small Tests Beat a Complete Funnel Overhaul

13:45 How to Set Realistic Funnel Expectations With Clients

15:30 When You Need to Push Back on Your Client

18:40 The Biggest Funnel Mistakes Marketers Make

20:45 Stop Chasing Marketing Shiny Objects

21:30 Why You Can’t Copy Someone Else’s Funnel

23:20 Selling High-Ticket Offers Requires More Trust

24:05 How to Use AI to Build Better Funnels

26:10 Where AI Falls Short With Marketing Strategy

27:20 What’s Outdated in Funnel Marketing?

28:50 The Secret to a High-Converting Funnel

29:15 Build a “Safety Net” Into Every Funnel

30:00 The Most Underrated Funnel Page

30:55 What Digital Marketers Can Learn From E-Commerce

31:15 Cheyenne’s Dream Funnel Client

31:50 Where to Connect With Cheyenne

I got an email recently that really made me think. It was from someone who turned down an unpaid speaking opportunity within my program, firmly stating that they don’t work for free - and honestly? I respect that. I’ve always been a big advocate for charging what you’re worth.

But here’s the thing…some of the biggest opportunities in my career started as unpaid. Speaking engagements, free power hours, strategic collaborations – when done intentionally – have led to massive payoffs (I’m talking six-figures-from-one-client kind of payoffs).

So in this episode, we’re digging into:

• When it actually makes sense to say yes to an unpaid opportunity
• The questions I ask myself before deciding
• A real story of how one free power hour turned into over $200,000 in revenue from one client

If you’ve ever wrestled with the “should I do this for free?” debate, this one’s for you. Let’s get into it.

TIMESTAMPS:

00:00 When Working for Free Can Actually Pay Off

01:00 How Free Work Led to $200K+ in Revenue

01:35 Why “Never Work for Free” Isn’t Always the Answer

02:40 Charging Your Worth vs. Playing the Long Game

03:30 The 5 Questions I Ask Before Working for Free

03:45 #1: Does It Put You in Front of Your Dream Audience?

04:20 #2: Could It Lead to Paid Work or Valuable Relationships?

05:15 How Free Work Turned Into a Long-Term Client

05:40 The Free Marketing Audit That Led to $200K+

06:20 #3: Do You Actually Want to Do It?

07:10 #4: Does It Align With Your Bigger Goals?

08:00 Why I Rarely Turned Down Speaking Opportunities

09:20 #5: Would You Regret Saying No?

10:10 What Should a Fractional CMO Consider Doing for Free?

10:25 Free Power Hours & Marketing Audits

11:15 Speaking, Advising & Board Opportunities

12:10 When You Should—and Shouldn’t—Work for Free

13:00 Sometimes Free Work Is the Smartest Long-Term Move

Paid ads can be a game-changer - but only if you know how to hire and manage the right team. As a Fractional CMO or marketing leader, your job isn’t to run ads—it’s to hire and manage an agency that can deliver results for your clients.

In this episode, I sit down with Jennifer Spivak, CEO of The Ad Girls, to break down exactly how CMOs can make paid ads work as part of a larger marketing strategy. Jennifer and I have worked together on countless client accounts, and she’s sharing her best insights on how to hire the right agency, manage the relationship, and ensure paid ads actually drive revenue.

We’re covering:

-The biggest mistakes marketers make with paid ads (and how to avoid them)

-How to vet and hire an ad agency for your clients—what to ask, what to look for, and what to avoid

-How to manage and collaborate with an agency as a Fractional CMO to drive better results

-Scaling your business as a marketer or Fractional CMO—Jennifer has built a powerhouse agency, and she’s sharing what it really takes to scale successfully

If you’re a marketer looking to step into CMO-level leadership, knowing how to hire and work with paid ad agencies is a skill you need. And if you’re looking to scale your own business, Jennifer’s insights from building and leading a wildly successful agency are invaluable.

TIMESTAMPS:

00:00 How Fractional CMOs Should Approach Paid Ads

01:25 The Biggest Myth About Paid Ads

02:35 When Is Your Business Ready for Paid Ads?

03:10 How Long Should Paid Ads Take to Work?

04:45 What Marketers Actually Need to Know About Paid Ads

05:20 Don’t Let an Ads Agency Intimidate You

06:45 Paid Ads Are Still Just Marketing

07:30 The Paid Ads Mistake That Wastes the Most Money

09:05 Stop Blaming the Algorithm

10:45 How to Hire the Right Paid Ads Agency

11:50 Good vs. Great Paid Ads Agencies

13:20 Why Ads Can’t Work in a Silo

15:45 Why Full-Service Agency Support Matters

16:15 Questions to Ask Before Hiring an Ads Agency

17:40 Does Your Ads Agency Need Industry Experience?

18:45 What Makes a Great Agency Client?

20:05 How to Manage Your Paid Ads Agency

21:25 The Agency Red Flags You Shouldn’t Ignore

23:10 Trust Your Instincts When an Agency Feels Off

23:45 How Jennifer Built & Scaled The AdGirls

24:20 The Hardest Part of Growing an Agency

25:40 The 25-Step Hiring Process That Changed Everything

27:55 How Long Does It Take to Build a Great Team?

28:50 Stop Assuming Other Experts Have the Answer

30:50 There Is No Secret Behind the Curtain

31:15 Jennifer’s Biggest Agency Scaling Mistake

32:45 How to Grow Beyond Being a Solopreneur

34:10 How to Remove Yourself From Client Delivery

35:25 You Can’t SOP Great Strategic Thinking

35:45 Where to Connect With Jennifer

Ever had a moment as a marketer where you thought, I hate marketing? You’re not alone. I’ve been there - more than once. But every single time, it wasn’t marketing itself that I hated - it was the wrong job, wrong boss, or doing work that didn’t align with what I loved.

In this episode, I’m joined by my longtime friend, Jessica Turner, who started her career in marketing with me but ultimately took a different path, stepping into product strategy. She’s seen my entire evolution — from fresh-out-of-university marketer to Fractional CMO — and today, she’s helping me break down the biggest reasons marketers feel stuck, how to tell if you’re in the wrong role, and how to pivot into work that actually excites you.

If you’re feeling burned out, uninspired, or questioning your career, this episode will help you figure out what’s really going on—and what to do about it.

Ready to take the next step?

If you’re ready to step into the Fractional CMO role but want support as you do it, Fractional CMO School is a 6-month coaching program + community to help you confidently land high-ticket clients and build a 6-figure (and beyond) business as a Fractional CMO.

Start or scale as a Fractional CMO → https://fractional-cmo-school.com

TIMESTAMPS:

00:00 Do You Actually Hate Marketing?

01:20 Where Our Marketing Careers Started

02:05 Why Jess Turner Left Marketing for Product Strategy

03:10 When “I Hate Marketing” Actually Means Something Else

04:05 The Work That Made Me Dread My Job

05:00 I Seriously Considered Leaving Marketing

06:00 You Don’t Need to Have Your Whole Career Figured Out

06:40 The Career Red Flags I Used to Ignore

07:35 Stop Making Career Decisions Based on “Should”

09:15 How I Started Building a Career Around the Life I Wanted

10:00 The Unexpected Job That Changed My Career

12:00 Starting a Business on Maternity Leave

13:10 You Don’t Need to Know Exactly What Your Business Will Be

14:15 Every Career Experience Teaches You Something

14:35 How I Figured Out What I Actually Loved Doing

16:00 Discovering the Fractional CMO Role Changed Everything

17:00 Being a Marketing Generalist Is a Superpower

18:05 What My Work & Life Look Like Now

19:30 The Fears I Had Becoming a Fractional CMO

20:25 You Don’t Need to Know Everything as a CMO

22:00 What to Do If You Feel Stuck in Marketing

23:00 Take Baby Steps Before Making a Huge Career Change

24:00 Do You Hate Marketing—or Just Your Current Role?

25:00 What I’d Tell My Younger Self About Her Career

26:00 You Can Always Change Your Mind

26:25 Trust the Process & Keep Taking the Next Step

27:20 Build Your Fractional CMO Business Faster

What actually happens in the first 90 days when a Fractional CMO steps into a business? Where should the focus be? How do you know if it’s working? In this episode, I’m pulling back the curtain on my exact process—from the deep-dive audit that reveals hidden opportunities to the quick wins that drive immediate results, to building a marketing strategy that sets the foundation for long-term growth. Whether you're hiring a Fractional CMO or stepping into the role yourself, this episode breaks down what to expect, what matters most in those first 90 days, and how to ensure you’re making an impact fast.

• Fractional CMO School - Fractional CMO School is a six-month coaching program + community designed to help you launch your business, attract dream clients, and build the business you've always dreamed of.
• Find me on LinkedIn
• Find me on Instagram
• Strategic Marketer Assessment - Unlock access to my free self-assessment for marketers who are juggling too much and want to work less while earning more.

TIMESTAMPS:

00:00 What Happens in the First 90 Days With a Fractional CMO?

01:05 Month 1: The Deep-Dive Marketing Audit

02:30 What I Audit in a Client’s Business

03:00 Start With Your Ideal Customer

04:25 Audit Your Offers & Find the Gaps

05:25 Find the Leaks in Your Marketing Channels

06:15 Stop Guessing & Start Tracking Your Data

07:15 Build Your 90-Day Marketing Roadmap

08:00 Month 2: Focus on Quick Wins & ROI

08:45 Month 3: Review, Learn & Adjust the Strategy

10:05 What We Actually Do in the First 90 Days

10:20 How We Generated Six Figures in 4 Days

11:00 Build the Marketing Foundations First

11:35 Find Where Your Marketing Budget Is Being Wasted

12:05 How We Saved a Client $15K a Month

12:50 Find the Leads Falling Through the Cracks

13:45 Make Sure Your Fractional CMO Scope Is Right

14:25 Does the Client Have the Right Marketing Team?

15:35 Why Client Check-Ins Matter

16:00 Get Feedback From the CEO, Team & Agencies

The term Fractional CMO is everywhere right now, but let’s be real—most people have no idea what it actually means. If you’ve been wondering, Is this just a fancy name for a marketing consultant? Do they run my ads? Why would I hire one instead of a full-time CMO?—this episode is for you.

I’m breaking down exactly what a Fractional CMO does, what they don’t do, and why so many businesses hire one for the wrong reasons. We’ll talk about when you actually need a Fractional CMO, how they fit into your business, and how to spot the difference between a true strategic leader and someone just slapping the title on their LinkedIn profile.

If you’re a business owner thinking about hiring one - or a marketer wondering if this could be your next career move - this episode is your roadmap.

• Fractional CMO School - Fractional CMO School is a six-month coaching program + community designed to help you launch your business, attract dream clients, and build the business you've always dreamed of.
• Find me on LinkedIn
• Find me on Instagram
• Strategic Marketer Assessment - Unlock access to my free self-assessment for marketers who are juggling too much and want to work less while earning more.

TIMESTAMPS:

00:00 What Is a Fractional CMO, Anyway?

01:00 The Simple Definition of a Fractional CMO

02:00 What Does a Fractional CMO Actually Do?

03:00 Think Like a Business Leader, Not Just a Marketer

04:00 What a Fractional CMO Does NOT Do

05:00 A Fractional CMO Is Not a Project Manager

05:30 When Does a Business Actually Need a Fractional CMO?

06:20 A CMO Can’t Fix a Broken Business

07:10 The Clients I Look for as a Fractional CMO

07:35 What Fractional CMO Support Looks Like in Real Life

09:00 Could You Become a Fractional CMO?

09:15 You Don’t Need to Know Everything About Marketing

10:00 Stop Executing & Start Leading

11:00 Why I Love the Fractional CMO Model

11:25 More Control Over Your Time, Income & Career

Welcome to CMO School, the go-to podcast for marketers who are ready to level up. I’m Jess Shirra, a Fractional CMO, marketing strategist, and founder of Fractional CMO School. After 15+ years leading marketing for brands like Lululemon, Pottery Barn, Strava, Jenna Kutcher, and Lori Harder, I’m here to pull back the curtain on what it really takes to drive growth, lead strategy, and step into your next chapter.

Expect expert insights, real talk about what works (and what doesn’t), and actionable strategies to help you think like a CMO—whether you’re climbing the ladder or building your own Fractional CMO business. This is the CMO School podcast.

• Fractional CMO School - Fractional CMO School is a six-month coaching program + community designed to help you launch your business, attract dream clients, and build the business you've always dreamed of.
• Find me on LinkedIn
• Find me on Instagram
• Strategic Marketer Assessment - Unlock access to my free self-assessment for marketers who are juggling too much and want to work less while earning more.