CMO School

Jessica Shirra | Fractional CMO
  • 5.0 (5)
  • Marketing
  • Weekly

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.

  1. 1d ago

    How I Retrained My Brain to Become Who I Wanted to Be

    Have you ever watched someone on a stage or on video and thought, "I could never do that"? That was me. Early on in my business, I told my coach I just wasn't the kind of person who could have a podcast. I was scared to charge more, scared to use my voice, and for years I thought that was just who I was. But it turns out I was wrong, and you're listening to that podcast right now. This is how I retrained my brain to become the person I wanted to be, because I really believe the only thing standing between you and who you want to be is you. In this episode, I'm sharing: The beliefs I had about myself when I started my business, and how they kept me charging less and staying quiet for YEARSThe moment I realized my lack of confidence wasn't my personality at all (and it started with a session I was SO sure wouldn't work on me)The four things I did to completely change how I see myself, including one I know sounds a little out thereHow it changed everything in my business, from the way I sell to what I charge to the kind of leader I am nowThe thing that still scares me today, and what I do when the fear comes back, because it always does Whether you're a Fractional CMO, a consultant, or a marketer still working up the courage to go out on your own, if there's a version of you that you've been telling yourself you could never be, 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 Retrained My Brain to Become Who I Wanted to Be 00:45 The Limiting Beliefs That Held Me Back 01:40 The Mindset Experience That Changed Everything 02:50 How I Realized I Could Rewire My Thinking 03:25 #1: Get Support to Change Your Mindset 04:40 Why Changing Deep-Rooted Beliefs Is So Hard 05:35 #2: Surround Yourself With People Who Inspire You 06:45 Turn Comparison Into Proof of What's Possible 07:45 #3: Start Before You Feel Ready 08:40 #4: Give Yourself Permission to Be Bad 09:40 Why Consistency Builds Confidence 10:40 How I've Changed My Life & Business 11:35 From Replacing My Salary to Earning 5X More 12:20 How Mindset Work Changed My Leadership & Boundaries 13:15 Why Imposter Syndrome Never Fully Goes Away 14:10 Stop Letting Fear Dictate What's Possible 14:50 You Can Become the Person You Want to Be 15:15 Mindset & Leadership Support Inside Fractional CMO School

  2. Nov 3

    When Is the Right Time to Hire a Fractional CMO? (Earlier Than You Think)

    So, when IS the right time to hire a Fractional CMO? My answer is a lot earlier than most founders think. And yes, I know, of course the Fractional CMO thinks you should hire a Fractional CMO. But I've seen what waiting costs a business, and it's usually more than hiring one would have. I'm breaking down exactly how I decide, so founders know if they're ready and marketers know what to say when a lead isn't sure. In this episode, I'm sharing: Why so many founders think they're "too early" (and why I see it so differently)The three things I look at to decide if a business is ready, and the one that's a dealbreakerWhat it really costs a business to wait, from the hires you make to where your marketing budget goesWhen I'd tell a founder to hold off, because sometimes it really is too soonFor the marketers: what to say when a lead tells you it's not the right time yet Whether you're a founder wondering if it's time to bring in marketing leadership, or a marketer who keeps hearing "not yet" from the clients you want to work with, 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/ What I Do and Don’t Do: Hiring Edition podcast TIMESTAMPS: 00:00 When Is the Right Time to Hire a Fractional CMO? 00:50 Why You Should Hire a Fractional CMO Earlier Than You Think 01:35 Benefit #1: Hire the Right Marketing Team in the Right Order 02:45 Benefit #2: Stop Wasting Money on the Wrong Marketing 03:30 The $30K Marketing Mistake You Can Avoid 04:25 Benefit #3: Avoid Costly Mistakes & Grow Faster 05:30 What to Say When a Client Thinks It's Too Early 06:15 Why Advisory Support Can Be a Great Starting Point 07:10 The 3 Signs a Business Is Ready for a Fractional CMO 07:30 #1: Does the Business Have Proven Traction? 08:40 When a Business Is Too Early for a Fractional CMO 09:15 #2: Is There Someone to Execute the Marketing Strategy? 10:15 Why I Prefer Helping Clients Build Their Marketing Team 11:00 #3: Does the Business Have the Budget? 12:05 How to Know If It's the Right Time to Hire 12:35 Build Your Fractional CMO Business With Confidence

  3. Oct 27

    Why You're Not Closing Clients as a Fractional CMO (It's Not Your Price)

    If you've ever lost a client you really wanted and thought, "Maybe I'm just bad at sales," this episode is for you. I hear this ALL the time, and listen, I get it. Selling felt pushy to me for a long time too. But you are not bad at sales, and you definitely don't need to knock two thousand dollars off your retainer. So I'm walking you through how I take a potential client from the very first conversation to a signed contract, step by step, so you can sign more of the clients you want without lowering your rates or feeling pushy. In this episode, I'm sharing: The seven places I see Fractional CMOs lose a client they should have signed (and how to figure out which one is costing you the most)The prep I do before every sales call, and why it changes the whole conversationHow I say my price out loud, because HOW you say it matters just as much as the numberWhat I say when a client tells me it's too expensive, needs to "think about it," or has to "run it by their partner"How I ask for the sale and follow up without feeling pushy, annoying, or like I'm chasing Whether you're a Fractional CMO, a consultant, or a marketing contractor, if you want to sign more of the clients you're already talking to without lowering your rates, 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 Why You're Not Closing Fractional CMO Clients (It's Not Your Price) 00:55 Why “You're Too Expensive” Isn't the Real Problem 02:05 #1: You're Not Pre-Qualifying Your Leads 03:30 #2: Your Discovery Calls Are Too Surface-Level 04:45 #3: You're Emailing Proposals Instead of Selling Them 06:15 Why Your Proposal Needs a Sales Call 07:30 #4: You're Not Confident When Sharing Your Price 08:45 Say Your Price & Stop Talking 09:50 #5: You're Not Handling Sales Objections Properly 11:00 How to Respond When Clients Say They Need Execution 12:45 Stop Being Afraid to Push Back on Clients 14:00 #6: You're Not Asking for the Close 15:10 How to Uncover Hidden Sales Objections 15:55 #7: You're Not Following Up Enough 17:05 Why I Follow Up Until I Get a Clear No 18:00 Audit Your Last 3 Lost Sales Opportunities 18:45 Improve Your Sales Process & Close More Clients

  4. Oct 20

    Growing Your Business as a Marketer: How to Build a Team Without the Overhead

    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

  5. Oct 13

    How to Become More Valuable as a Marketer in the Age of AI

    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

  6. Oct 6

    How to Find Fractional CMO Clients in 2026 - 12 Proven Ways

    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

  7. Sep 29

    How Many Hours Should a Fractional CMO Work Per Client?

    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

  8. Sep 22

    When Things Feel Hard: 5 Strategies to Help You Get Out of a Rut

    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

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About

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.

Information

  • Creator
    Jessica Shirra | Fractional CMO
  • Years Active
    2025 - 2026
  • Episodes
    72
  • Rating
    Explicit
  • Copyright
    © Copyright 2026 Jessica Shirra | Fractional CMO
  • Show Website
    CMO School

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