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CMO School

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Rating
★★★★★
5
from
5 reviews
This podcast has
69 episodes
Language
English
Date created
2025/02/21
Latest episode
2026/10/20
Average duration
19 min.
Release period
8 days

Description

CMO School is the go-to podcast for marketers and Fractional CMOs ready to step into leadership, own their expertise, and build a career or business that actually works for them. Whether you're looking to elevate your skills, transition into a CMO role, or scale your Fractional business, this podcast delivers strategies, expert insights, and the mindset shifts you need to create a career you love. Hosted by Jess Shirra—a 15+ year marketing leader, Fractional CMO, and founder of Fractional CMO School—this show takes you behind the scenes on what actually works in marketing, business, and leadership. Jess has worked with powerhouse brands and creators like Lululemon, Pottery Barn, Strava, Jenna Kutcher, Lori Harder, and more—and now, she’s sharing those lessons with you. Each episode, we dive into proven strategies, practical insights, and candid conversations on topics like: How to step into leadership as a marketer and own your expertise How to confidently price your services and build a business that supports the life you want What it really takes to succeed as a Fractional CMO How to show up as a CMO for your clients, deliver powerful strategy, and lead teams effectively Lessons from experts across marketing, mindset, and entrepreneurship to help you grow Whether you're a corporate marketer exploring the Fractional path, a new Fractional CMO figuring it all out, or a seasoned leader looking to scale and systematize your business, CMO School will give you the tools, insights, and confidence to create a career that gives you freedom, fulfillment, and flexibility—on your terms. New episodes drop weekly! Subscribe now and start building a marketing career that lights you up.

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Check latest episodes from CMO School podcast


Growing Your Business as a Marketer: How to Build a Team Without the Overhead
2026/10/20
At some point in your marketing business, you can't do all of the work yourself anymore. A client needs copy, or design, or paid ads, and now you have to decide who you trust enough to put in front of them. And that's the hard part of building a team, because whoever you bring in, their work goes out under YOUR name. I've gotten this wrong. I've made three big hiring mistakes over the years, and one of them ended with a contractor taking my money and ghosting me. So in this episode, I'm walking you through how I hire now. In this episode, I'm sharing: The one rule I have for anyone who works under my nameWhat I ask for before I'll hire someone I don't knowThe four things I look for in every single person I hireWhat the first few months look like once someone is on my teamWhy the traditional agency model isn't for meWho is on my team right now, and how I handle the financial side Whether you're a marketing contractor bringing on your first subcontractor, a Fractional CMO building a bench of people you can call on, or you're helping a client hire, you’ll love this episode. 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/ Web/Branding Designer: Ria Johnston → https://studio-kind.com/about TIMESTAMPS: 00:00 How to Build a Marketing Team Without the Overhead 01:15 Why I Don't Run a Traditional Marketing Agency 02:30 How I Structure My Subcontractor Team 03:35 Why I'm So Selective About Who I Hire 04:45 My 2 Rules for Hiring Subcontractors 06:10 The Hiring Mistake That Cost Me a Vacation 07:10 How I Make Money From Subcontractors 08:30 How I Structure Contractor Payments 09:45 Who's Actually on My Marketing Team? 10:10 Why Hiring My Best Friend Works 12:20 How Fractional CMOs Work Within My Agency 13:15 The Marketing Specialists I Keep on My Team 14:35 How I Find Great Contractors Without Recruiting 16:05 My Process for Hiring New Team Members 16:45 Why I Always Start With a Paid Test Project 17:45 The 4 Things I Look for in Every Hire 18:00 #1: Skills & Quality of Work 18:45 #2: Strategic Thinking & Problem-Solving 20:20 #3: Reliability & Accountability 20:55 #4: Professionalism & Communication 21:35 How I Onboard Contractors for Long-Term Success 23:15 Why Setting Expectations Early Saves Time Later 24:00 What to Do When a Contractor Isn't Working Out 25:05 Who Should You Hire First? 26:00 Start Building Your Team With People You Trust 27:00 My Advice for Growing Your Team Slowly 28:15 Grow Your Fractional CMO Business Without the Overhead
How to Become More Valuable as a Marketer in the Age of AI
2026/10/13
AI is getting better at doing the work marketers have been paid to do for years. And whether you’re a Fractional CMO, a strategist, a consultant, or working on a marketing team, I think there’s a question worth asking now: What is going to make you MORE valuable as AI gets better? Because I don’t think the marketers who thrive over the next five or ten years will necessarily be the ones who can produce the most, work the fastest, or even use the most AI tools. There’s a much bigger shift happening in what great marketing is worth, and where companies are going to need humans most. In this episode, I’m sharing: The shift I think is going to have one of the biggest impacts on marketing careers over the next few yearsWhy some incredibly talented marketers may still find their value getting squeezedWhere I believe the biggest opportunity is for marketers who want to become more valuable, not lessWhat I would be paying very close attention to if I were building my marketing career todayOne question you can use to look at your own work and see whether you’re moving in the right direction I don’t know exactly what AI will be capable of five years from now. None of us do. But I do think we can already see where things are heading. And if you work in marketing, I think understanding this shift now could completely change what you choose to get really, really good at next. 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 Will AI Make Your Marketing Skills Less Valuable? 00:40 The Marketing Work AI Is Making Less Valuable 02:30 Why Execution Alone Is No Longer Enough 04:05 Where the Real Value in Marketing Is Moving 05:30 The 3 Skills That Make Marketers More Valuable 05:55 #1: Know What Marketing Is Actually Worth Doing 07:20 #2: Develop Better Taste & Strategic Judgment 09:35 #3: Make Confident Marketing Decisions 11:50 How to Make Your Marketing Expertise More Valuable 12:50 Stop Selling Deliverables & Start Showing Your Strategy 14:20 Show Clients the Thinking Behind Your Work 15:35 The “So What?” That Makes Your Reporting Valuable 16:40 Stop Being an Order Taker & Start Leading 17:50 Use Your Expertise to Improve AI-Generated Work 18:55 The Career Exercise Every Marketer Should Do 20:15 Find the Work That Energizes You 21:15 Should You Move Into Marketing Leadership? 22:10 How to Stay Valuable If You Love Execution 22:55 The Opportunity AI Creates for Marketers 23:25 Build Your Strategic Marketing Skills With Fractional CMO School
How to Find Fractional CMO Clients in 2026 - 12 Proven Ways
2026/10/06
There are WAY more ways to find Fractional CMO clients than you probably realize. I've personally used 12 different strategies to find clients over the years, which is exactly why I don't believe there is one "right" way to build your pipeline. And in this episode, I'm breaking all 12 of them down. I'm sharing: How I think about finding clients before I ever start looking for themThe two client acquisition strategies I personally wouldn't prioritize, and where I'd put that energy instead12 different ways I've actually found Fractional CMO clients throughout my careerA 13th, AI-focused bonus strategy I'm experimenting with right nowThe exact steps I'd take to turn all of these options into an actionable client acquisition plan The best part is that you don't need a massive audience, a complicated funnel, or one perfect lead generation strategy to build a strong pipeline. You need to know where the opportunities are, choose where you're going to focus, and consistently put yourself in the right places. By the end of this episode, you'll have plenty of ways to do exactly that, plus a clear plan for what to do next. FREE cold outreach email templates: Fractional CMO Sales Email Templates — The CMO Office 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 12 Ways to Find Fractional CMO Clients in 2026 01:05 Don’t Lower Your Standards Just Because You Need Clients 02:15 2 Client-Getting Strategies I Would Skip 02:25 Why I Wouldn’t Start With Paid Ads 03:15 Why Cold DMs Don’t Work for High-Ticket Services 04:05 #1: Cold Outreach to Dream Clients 06:15 How to Make Cold Outreach Actually Work 07:45 #2: Optimize Your LinkedIn Profile 09:20 #3: Post Strategic Content on LinkedIn 11:15 #4: Tap Into Your Existing Network 13:10 #5: Build Relationships With Other Fractional CMOs 14:30 #6: Connect With Advisors Around Your Ideal Client 16:05 #7: Build Referral Partnerships With Agencies 18:35 #8: Get in Front of Communities Your Clients Already Trust 20:30 #9: Be a Guest on the Right Podcasts 22:10 #10: Connect With Recruiters & Fractional Staffing Firms 23:50 #11: Use Job Sites & Fractional Marketplaces 25:25 Don’t Disqualify Yourself Before You Apply 26:15 #12: Use Upwork Strategically 27:25 BONUS: Get Found Through AI Search 28:35 Your 3-Step Plan to Start Getting Clients 28:50 Step 1: Pick Your 3 Best Lead Generation Tactics 29:20 Step 2: Set Measurable Weekly Goals 29:50 Step 3: Give Your Strategy Enough Time to Work 30:25 Stop Researching & Start Taking Action
How Many Hours Should a Fractional CMO Work Per Client?
2026/09/29
One of the biggest unlocks in my Fractional CMO business was realizing I could make more money by selling LESS of my time. Because if every new client requires another 10, 15, or 20 hours of your week, there's eventually a ceiling on how much you can earn. And if getting faster and better at your job means you simply have to take on more work to make more money... something about that model is broken. So in this episode, I'm getting really transparent about what the math actually looks like inside my Fractional CMO business. I'm sharing: Why I stopped thinking about Fractional CMO work in terms of billable hoursThe three problems I see with hourly pricing as you move into a leadership roleHow I structure and scope my packages insteadHow many hours I actually spend on different types of clientsThe effective hourly rate I aim for behind the scenesHow to know if you're spending way too much time on your own clients The goal isn't to squeeze more clients into an already packed calendar. It's to get really good at understanding the value of your time, protecting your scope, and building offers where the numbers actually work. Because the better you get at this work, the more valuable your time should become. And your business model should allow you to benefit from that. 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 How Many Hours Should a Fractional CMO Work Per Client? 01:05 Why I Don’t Charge Hourly 01:25 Reason #1: Hourly Pricing Rewards Inefficiency 02:30 Reason #2: Your Value Isn’t Your Time 03:45 Reason #3: Stop Trying to “Fill” Your Hours 05:00 How I Scope My Fractional CMO Packages Instead 06:25 My Target $300–$500 Effective Hourly Rate 07:05 How Many Hours I Actually Work Per Client 08:15 Advisory vs. Full Fractional CMO Hours 09:15 How to Know If You’re Working Too Much 09:45 #1: Look at Your Scope 10:25 #2: Look at Your Time 10:55 #3: Calculate Your Effective Hourly Rate 11:45 Make Your Hours Work for Your Business Model 12:25 Build a Business That Doesn’t Run You Into the Ground
When Things Feel Hard: 5 Strategies to Help You Get Out of a Rut
2026/09/22
You know those seasons where business (or life) just feels harder than it should? A few things haven't gone your way. You've lost some momentum. You're questioning decisions you normally feel confident about. And somehow, without really noticing when it happened, you just don't feel quite like yourself. I've been through enough of these seasons to know that there are a handful of patterns I fall into every single time. They seem small in the moment, but together they can keep me stuck in a rut for way longer than I need to be. In this episode, I'm sharing: The five patterns I watch for when business (or life) starts to feel hardThe subtle ways we can accidentally make a difficult season feel even heavierWhat I do differently now when I notice myself slipping into one of these patternsHow I start finding my way back to feeling clear, grounded, and like myself againThe questions I ask myself before making big decisions from a difficult headspace If you're in a season where you're overthinking everything, questioning what's next, or simply feeling a little off, this episode is for you. You might not be able to change everything that's happening around you right now. But there are things you can change about how you move through it, and sometimes that makes a much bigger difference than you'd expect. 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 What to Do When Everything Feels Hard 01:30 The Habits That Make Hard Seasons Even Harder 02:25 #1: Take Care of Your Body First 04:15 Start Small When Your Routine Falls Apart 06:00 #2: Stop Isolating Yourself 08:20 #3: Make Space to Actually Feel What You’re Feeling 10:35 Why Your Problems Feel Smaller When You Regulate Yourself 11:10 #4: Get Outside of Your Own Head 13:10 Helping Someone Else Can Shift Your Perspective 13:55 #5: Stop Believing Every Thought You Have 15:35 Separate the Facts From the Story You’re Telling Yourself 16:50 Borrow Confidence From Your Past Self 17:45 Don’t Make Big Decisions From a Bad Headspace 18:35 Get Back to Yourself Before You Fix the Problem
How to Think Like a CMO: 6 Laws for Better Marketing Strategy
2026/09/15
Anyone can put together a deck full of marketing recommendations. Building a strategy that actually feels like it came from a really good CMO requires a completely different level of thinking. Over the years, I've realized there are a handful of principles I come back to every single time I'm building strategy for a client. They've changed the way I make recommendations, how I work with founders, and honestly, how confident I feel making the calls I'm being paid to make. This week's episode is actually pulled from a training I taught inside Fractional CMO School, and I'm walking you through what I call the Six Laws of CMO-Level Strategy. In this episode, we're covering: The six laws I use when building high-level marketing strategy for clientsHow to start thinking like the person leading marketing instead of simply doing the marketingThe common mistakes that can make an otherwise solid strategy feel more junior or execution-focusedHow to develop stronger strategic judgment when there isn't one obvious "right" answerHow to make recommendations you can actually stand behind and communicate confidently to your clients The more you develop this way of thinking, the easier it becomes to walk into a business, see what's actually going on, know where to focus, and make the calls your clients are looking to you to make. And that's such a huge part of stepping into the CMO role with confidence. You trust your thinking more, your clients trust your recommendations more, and you start showing up as the person who can actually lead the marketing. 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 The 6 Laws of a CMO-Level Marketing Strategy 01:14 How to Think Like a Marketing Leader 01:55 Law #1: Think Like an Owner, Marketer Second 05:25 Law #2: Your Client Is an Unreliable Narrator 08:10 Law #3: Trust Your Strategic Instincts 10:40 Law #4: Be a Leader, Not an Order Taker 14:40 The Client Mistake That Taught Me to Speak Up 16:35 Law #5: Right-Size Your Strategy to Their Resources 18:50 Law #6: Know When to Zoom In & Zoom Out 20:20 Stop Overcomplicating Your Marketing Strategy
Sometimes I Feel Like I'm Bad at Marketing (And I Know It's Not Just Me)
2026/09/01
Ever found yourself questioning whether you're actually good at marketing? Maybe you had a client launch go poorly, or they were unhappy with their marketing results. Either way…cue existential crisis. It doesn't matter how much experience you have – most marketers go through periods where they lose confidence in themselves. It's easy to assume the problem is you, when it’s usually just a mismatch in expectations. The more I've spoken to marketers over the years, the more I've realised this isn't just my experience. So many of us carry this around, but very few of us actually talk about it. In this week's episode, I'm unpacking: Why self-doubt is SO normal, even if you're experiencedThe three growth phases every business experiences AND what happens in marketing at each phaseThe framework I use to regain my confidence when I'm starting to feel imposter syndrome creep in If you've ever found yourself lying awake wondering whether you've still "got it," or questioning everything after a few disappointing weeks, I really hope this episode reminds you that you're probably doing better than you think. 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 Do You Ever Feel Like You're Bad at Marketing? 01:20 Why Even Experienced Marketers Lose Confidence 03:00 The Real Problem Isn't Your Marketing 04:20 Phase 1: Build 06:45 Phase 2: Stabilize 09:20 Phase 3: Grow 11:10 Why Most Businesses Stay Stuck 12:20 Ask This Before You Change Your Strategy 13:20 Stop Measuring Success Against the Wrong Phase 14:00 You're Probably Doing Better Than You Think
3 Ways to Grow Your Marketing Business Without Working More Hours
2026/08/25
If you've built a successful marketing business, you've probably realised that making more money often means taking on more clients, more projects or working more hours. And at some point, you stop wanting that. The problem is, most marketers only see one obvious next step: build an agency. But that's not the right path for everyone. In this episode, I'm talking about the three different directions experienced marketers can take when they want to keep growing—and why I think the better question isn't, "How do I grow my business?" It's, "What kind of business do I actually want to build?" Because the business you build next should fit the life you want, not just your revenue goals. 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/ FRACTIONAL CMO START UP GUIDE: https://www.thecmooffice.com/fcmo-guide BOOK A CALL → https://calendly.com/the-cmo-office/fcmos-clarity-call TIMESTAMPS: 00:00 How to Grow Without Working More 01:10 The Question That Changes Everything 02:35 Option 1: Become the Premium Solo Expert 04:50 Why I Didn't Choose the Solopreneur Path 06:10 Option 2: Build an Agency 08:00 Why an Agency Wasn't Right for Me 09:00 Option 3: Become a Fractional CMO 11:20 Why I Chose the Fractional CMO Model 13:00 Which Business Model Fits Your Life? 14:10 Build a Business You Don't Want to Escape
Thinking About Becoming a Fractional CMO? 5 Fears About the Role (That Aren't Actually True)
2026/08/18
Thinking about becoming a Fractional CMO but worried you'll be on Slack all day, stuck in back-to-back meetings, and responsible for absolutely everything? I hear these concerns from marketers all the time. And honestly? Almost every one of them comes from a misunderstanding of what the Fractional CMO role actually is. In this week’s episode, I'm breaking down: The 5 biggest myths that stop great marketers from stepping into the Fractional CMO roleWhy so many Fractional CMOs end up creating a business that burns them outThe difference between being a strategic leader and becoming another member of the marketing teamWhat the role should actually look like inside a client's businessAnd how to build a Fractional CMO business that's sustainable, profitable, and gives you the freedom you were looking for in the first place If you've ever thought, "I'd love to become a Fractional CMO... but I don't want to be responsible for everything," this episode is 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 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 The 5 Biggest Myths About Becoming a Fractional CMO 01:05 Myth #1: You'll Spend All Day in Slack 03:10 Myth #2: You're Responsible for Everything 05:45 Why CMOs Lead Instead of Execute 06:45 Myth #3: Every Client Emergency Is Your Emergency 09:00 Myth #4: You'll Spend All Day in Meetings 11:30 Set Boundaries Before Clients Set Them for You 12:30 Myth #5: Clients Expect You to Do Everything 14:15 Teach Clients How to Work With You 15:35 Build a Fractional CMO Business That Gives You Freedom
Miranda Doubled Her Income Working Less as a Fractional CMO
2026/08/11
What if you could leave your full-time job, work fewer hours, and nearly double your income - all while doing work you actually love? In this episode, I’m joined by Fractional CMO School alum Miranda Holland to talk about how she went from working 40+ hours a week, to doubling her income, working just 30 hours a week as a Fractional CMO. Before Fractional CMO School, Miranda found herself reacting to whatever marketing requests her clients had, instead of steering the process and strategy. Fractional CMO School gave her the framework she needed to step into leadership and create the spacious business she’d always wanted. In this episode we cover: The frameworks that helped her package, position, and price her expertiseWhat gave her the confidence to leave her full-time job and go all-in on her businessHow she realized she was undercharging – and how her perspective on pricing changedThe mindset and imposter syndrome work that came with becoming an entrepreneur and CMOWhat her business and life look like now that she has more control over her time, income, and capacity If you’re curious about Fractional CMO School, and want to hear all about Miranda’s transformation from employee to Fractional CMO, you’ll love this episode. 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 Meet Miranda: From Corporate Marketer to Fractional CMO 02:30 Taking the Leap & Leaving Her Full-Time Job 04:05 The Framework That Gave Her Confidence 06:08 From Order Taker to Marketing Leader 08:06 Building a Fractional CMO Offer 09:41 The Results: Double the Income, Fewer Hours 12:45 The Mindset Shift Behind Her Success 15:38 Overcoming “Am I Qualified?” Imposter Syndrome 17:02 Packaging & Pricing Your Expertise 19:13 Why a Fractional CMO Can Be an Early Strategic Hire 21:21 Stop Selling Tactics - Start Looking at the Big Picture 22:34 Miranda’s Advice for Aspiring Fractional CMOs 23:11 Why Fractional CMO School Was Worth It
She Left Her "Dream Job" to Bet on Herself - And 6x'd Her Income
2026/08/07
I think a lot of us have been there, - sitting in a job that looks amazing from the outside, the kind where people go "wow, you work THERE?" - and slowly realizing it's just not filling your cup anymore. That's exactly where my guest this week was. Sydney Hagel left a big-name corporate job to start The Cozy Agency, and just over a year in she's on track to 6x her income. But the part I loved most about our conversation is how real she gets about that first year - the mistakes, the imposter syndrome, and what it really took to get to where she is now. In this episode of the CMO School podcast, we get into: How Sydney Hagel knew it was time to leave corporate - and what made her quit with no planWhat her first year in business looked like (including the money mistakes she made)How she lands high-ticket clients (it’s SO much simpler than you might think)The one thing she cared about more than profit in year one - and why it ended up building her whole client rosterHow she went from "I'll never make good money again" to 6x-ing her income in a single year If you're waiting to feel ready before you go after the big thing - the new niche, the bigger client, the leap out of your 9 to 5 - this is a conversation I want you to hear. Because you don't have to have it all figured out. You just have to be willing to bet on yourself before it feels safe. Learn more about Sydney: Instagram LinkedIn GetCozy Learn more about Callan Faulkner, AI expert 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 Meet Sydney Kaye & What We're Covering 01:50 From Corporate Marketing to Entrepreneurship 05:10 Why We Both Left Corporate 08:15 Knowing It Was Time to Quit 11:50 The Fear (and Freedom) of Starting Your Own Business 15:00 Landing the First High-Ticket Client 18:25 Imposter Syndrome Never Really Goes Away 21:00 How High-Ticket Clients Lead to More High-Ticket Clients 25:25 Why You Can't Skip the Building Phase 27:00 The Mindset That Keeps You Going 29:10 Your "Why" Matters More Than Money 30:50 Where to Connect with Sydney
6 Red Flags I Screen For Before I Take On Any Client as a Fractional CMO
2026/07/28
I've watched smart, capable marketers and Fractional CMOs burn out, lose money, and start to wonder if the whole Fractional path was a mistake — all because they said yes to the wrong client. And I've done it myself, more times than I'd like to admit. Because the thing is, you cannot out-strategize a bad-fit client. It doesn't matter how good your boundaries, your packages, or your process are — if the person on the other side of the contract is the problem, you can't fix it. In this episode, I break down: The 6 red flags I screen for before I'll work with ANY client (steal my checklist!)How to spot a bad-fit client on the discovery call — before you're locked into a contract with themThe questions I ask that get my leads to reveal who they REALLY are (so I don’t have to find out the hard way)Why a bad-fit client can make you question whether you're even cut out for this role (spoiler: it's not you)How saying no to the wrong clients is what lets you get real results for the right ones The clients you turn down matter just as much as the ones you take on. Once you can see the red flags coming, your work gets way easier — and a lot more fun. 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 The Wrong Client Will Cost You More 00:45 Why You Can't Out-Strategize a Bad Client 01:30 Red Flag #1: They Blame Every Marketer 02:45 Red Flag #2: No Team to Execute 03:45 Red Flag #3: Shiny Object Syndrome 04:45 Red Flag #4: You're Expected to Save the Business 06:00 Red Flags #5 & #6: Unrealistic Expectations 07:45 How to Protect Your Time and Energy 08:45 Choose Clients Who Set You Up to Win
Will the Fractional CMO Model Work in My Niche?
2026/07/21
"Will the Fractional model actually work in MY niche?" — I get this question all the time. And it's the one that keeps people stuck: not starting, saying no to clients who'd be a great fit, or waiting to feel ready before they let themselves go for it. But here's what I want you to hear — the niche is NOT what makes the Fractional model work. What you're selling has nothing to do with the industry. It's YOU. It's your leadership. And that is valuable (and transferable) to any niche. In this episode, I’m breaking down: The 4 things that ACTUALLY tell you if a business is a fit for the Fractional model — and not one of them is the niche (steal the checklist!)The real reason marketers get stuck on the niche question and what you're REALLY saying when you ask "will this work in my niche?"What actually makes you feel ready for this role How I landed one of the biggest names in the online space as my very FIRST client in a niche I'd never worked in By the end of this episode, the niche question won't feel so important, because you'll know exactly what to look for instead. 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 Will the Fractional Model Work in Your Niche? 00:45 The Question You Should Be Asking Instead 01:30 The 4 Signs a Business Is Ready 02:30 Why Revenue and Budget Matter 03:45 Leadership Matters More Than Industry 05:00 Why Marketers Get Stuck on Niches 06:15 Your Skills Transfer Further Than You Think 07:00 Stop Waiting for the Perfect Niche
How I Structure My Contracts as a Fractional CMO (And Why I Make It Easy for Clients to Leave)
2026/07/14
Contracts are probably one of the least exciting things we could possibly talk about, BUT I get so many questions from marketers making the leap into Fractional CMO work and feeling completely overwhelmed by the contract side of things. OR not thinking about it at all… until something happens and they've got serious regrets. If your immediate thought is "cool cool cool, can I just copy yours?" 😂 — you absolutely can. I share exactly where you can grab all of my behind-the-scenes business systems in the episode! In this episode, I break down: How I structure my contracts after 5+ years of testing long-term, short-term, and month-to-month (steal the setup!)Why I DON'T lock clients into long-term contracts — and what I do insteadThe scope language that keeps you from ever being "in default" of your own contractThe tool I use to get a new contract out to a client in under 2 minutesThe sneaky little feature that gives me a heads up when a client might be about to give their notice And at under 10 minutes, it's probably the quickest (and least painful) way you'll ever learn about contracts. 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 I Don't Use Long-Term Contracts 01:15 The Contract Structure That Works Best 02:30 Protect Yourself From Scope Creep 03:45 The Contract Tool I Use for Every Client 04:45 My Favorite PandaDoc Feature 05:30 Final Thoughts on Better Client Contracts
How I'm Using AI as a Fractional CMO to Deliver $15K+ Marketing Strategies
2026/07/07
The advice to "use AI to work faster" is great (I've cut my $15K client strategy build time nearly in HALF) but it’s really easy to get generic output if you’re not careful. That’s why I’m breaking down the exact process I use to build my client strategies. In this episode, I break down: The 5-step process I use to build my $15K client strategies with AI (so you can set yourself up the same way)The biggest mistakes I see Fractionals making with AI in strategy work (the last one is the worst)How I set up my AI to get great output (instead of generic or AI sounding garble)How I use AI as a thought partner instead of having it do the thinking for me If you want to use AI for marketing strategy, or you already are, but you’re not happy with the output, you’ll love this episode. 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 How I Cut Strategy Time in Half With AI 01:00 The Biggest AI Mistakes Marketers Make 02:45 Build AI Context Before You Prompt 04:15 Turn Your Thinking Into Better Strategy 05:45 Show AI What Great Looks Like 07:00 Why I Build Strategies Section by Section 08:45 The Final Review Most People Skip 10:00 Use AI as a Thought Partner, Not a Strategist 11:00 The Biggest AI Mistake to Avoid

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5 out of 5
5 reviews
★★★★★
BigTuna400 2025/02/22
Jess is the best!
Very insightful and practical help. Thorough and easily digestible.
★★★★★
Sferrcrick 2025/02/22
Are you ready for it?
In true Jessica form, she over-delivers in this podcast—big reputation, big ideas, and even bigger impact. A must listen for CMOs and entrepreneurs.
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