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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Why You're Not Closing Clients as a Fractional CMO (It's Not Your Price)
Episode 70
Tuesday, October 27, 2026 • Duration 19:26
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 conversation
How I say my price out loud, because HOW you say it matters just as much as the number
What 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.
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
Growing Your Business as a Marketer: How to Build a Team Without the Overhead
Episode 69
Tuesday, October 20, 2026 • Duration 28:59
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 name
What I ask for before I'll hire someone I don't know
The four things I look for in every single person I hire
What the first few months look like once someone is on my team
Why the traditional agency model isn't for me
Who 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.
00:00 How to Build a Marketing Team Without the Overhead
How to Become More Valuable as a Marketer in the Age of AI
Episode 68
Tuesday, October 13, 2026 • Duration 24:20
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 years
Why some incredibly talented marketers may still find their value getting squeezed
Where I believe the biggest opportunity is for marketers who want to become more valuable, not less
What I would be paying very close attention to if I were building my marketing career today
One 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.
How to Find Fractional CMO Clients in 2026 - 12 Proven Ways
Episode 67
Tuesday, October 6, 2026 • Duration 31:35
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 them
The two client acquisition strategies I personally wouldn't prioritize, and where I'd put that energy instead
12 different ways I've actually found Fractional CMO clients throughout my career
A 13th, AI-focused bonus strategy I'm experimenting with right now
The 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.
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.
00:00 12 Ways to Find Fractional CMO Clients in 2026
How Many Hours Should a Fractional CMO Work Per Client?
Episode 66
Tuesday, September 29, 2026 • Duration 12:47
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 hours
The three problems I see with hourly pricing as you move into a leadership role
How I structure and scope my packages instead
How many hours I actually spend on different types of clients
The effective hourly rate I aim for behind the scenes
How 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.
00:00 How Many Hours Should a Fractional CMO Work Per Client?
When Things Feel Hard: 5 Strategies to Help You Get Out of a Rut
Episode 65
Tuesday, September 22, 2026 • Duration 19:14
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 hard
The subtle ways we can accidentally make a difficult season feel even heavier
What I do differently now when I notice myself slipping into one of these patterns
How I start finding my way back to feeling clear, grounded, and like myself again
The 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.
How to Think Like a CMO: 6 Laws for Better Marketing Strategy
Episode 64
Tuesday, September 15, 2026 • Duration 20:57
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 clients
How to start thinking like the person leading marketing instead of simply doing the marketing
The common mistakes that can make an otherwise solid strategy feel more junior or execution-focused
How to develop stronger strategic judgment when there isn't one obvious "right" answer
How 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.
Sometimes I Feel Like I'm Bad at Marketing (And I Know It's Not Just Me)
Episode 63
Tuesday, September 1, 2026 • Duration 15:11
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 experienced
The three growth phases every business experiences AND what happens in marketing at each phase
The 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.
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
3 Ways to Grow Your Marketing Business Without Working More Hours
Episode 62
Tuesday, August 25, 2026 • Duration 14:57
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.
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
Thinking About Becoming a Fractional CMO? 5 Fears About the Role (That Aren't Actually True)
Episode 61
Tuesday, August 18, 2026 • Duration 16:25
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 role
Why so many Fractional CMOs end up creating a business that burns them out
The difference between being a strategic leader and becoming another member of the marketing team
What the role should actually look like inside a client's business
And 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.
