Can you keep climbing the corporate ladder after it collapsed? 

Anna Wondany did. And so can fractional executives. 

After a $60M startup sprint and a merger that led nowhere, Anna could have chased another exec role – she already held multiple VP positions after all.

Instead, she built something better of her own. 

Today, Anna is a fractional CMO and the founder of Hey CMO, a fast-growing network for marketing leaders who want independence without isolation. 

In this episode, we talk about what it means to work fractionally, how to prevent your own competence from drowning you, and why always saying yes might be your smartest move. 

Let’s dive in. 

Let’s start with the basics. How do you explain to potential clients the value of what you bring as a fractional?  

Anna: Most people still don’t really know what “fractional” means. Other fractionals get it – we know what we’re offering. But on the client side, there’s still a big education gap. 

I’ll have conversations where someone says, “We need a fractional, someone to run marketing, send emails, do campaigns…” and I have to stop them.

I explain: my role isn’t to come in and execute tactics.

It’s to build the strategy that drives growth and clarity for your business. 

When I start conversations, I always lead with value, not time.

One other question that people ask first is, “What’s your hourly rate?” but I save that for the end. 

Instead, I talk about where they are in their business, what pain points they’re feeling, and what growth looks like for them – whether that’s launching a new product, entering a new vertical, or prepping for an acquisition. 

Then I frame the value proposition of a fractional: you’re getting a strategic leader, not a freelancer. You get the level of insight and leadership of a CMO without the full-time headcount, benefits, and overhead.

And that’s the competitive advantage. 

Over time, it’s gotten better.

More people understand it now than a few years ago. But it still requires education.

Every fractional out there needs to help define and communicate what the role really is – and where the boundaries are. 

That’s an important point about boundaries – because when clients realize how capable you are, they start to hand you everything. How do you avoid getting pulled into the weeds? 

Anna: It’s one of the biggest challenges fractionals face.

Clients will say, “Can you just handle this one thing?” and before you know it, you’re knee-deep in execution.

It’s quicksand, so you really have to set expectations right from the start. 

When I start an engagement, I present the strategy and then I follow it immediately with, “Who on your team can help us get this executed?” 

That single question creates the separation between me as the strategic driver and the team as the implementers.

It keeps everyone in their lane. And it makes the engagement smoother because everyone understands what I bring to the table and what I don’t. 

But it’s also about confidence.

You might be tempted to say yes to everything to prove your value, but over time you realize that the real value comes from staying at the level where you make the biggest impact. 

Some people worry that if they say yes to unpaid conversations or projects, they’ll be giving too much away. Why do you always say yes? 

Anna: That one’s personal for me.

Early on, a friend called and said, “Hey, I’m advising a company that’s struggling with marketing. They don’t really have a budget, but would you mind talking to them?” I was really busy but I said yes anyway. 

We got on the phone, and he told me all his pain points. I started brainstorming ideas right there and by the end of the call, he hired me.

That turned into one of my longest-running clients. 

I always say yes because you never know where the next opportunity will come from or what you’ll learn. Even if it doesn’t turn into paid work, you gain perspective, meet new people, and get clarity on what you want to do next. 

I’m also at the stage where money isn’t my only driver. Revenue matters, but it’s also the satisfaction of waking up every morning and doing what I love. 

Marketing has been in my DNA since I was a teenager walking around a mall doing surveys. I’ll go into a restaurant, look at a bad menu, and immediately start thinking about how to fix it.

That’s just how my brain works. 

When I say yes, I expand my surface area. And every time I do, something good comes out of it.

I truly believe that when you stop leading with a money mindset and instead lead with curiosity and generosity, great things follow. 

You meet amazing people, run into the right opportunities, and find a deeper level of satisfaction.

What We Can Learn from Anna Wondany: 

Skip the guesswork.

This guide gives you the playbook – how to price, package, and launch your fractional CMO offer. Plus outreach and retention strategies that actually work.

You’ll also get templates you can put to use before your coffee cools.

You blocked the time.  

You’ve got the tools.  

You’ve made peace with wearing the same shirt four videos in a row. 

Now comes the part that trips most people up: what the heck do I say? 

Here’s the good news: you don’t need to say something groundbreaking every time. 

You just need to be clear, useful, and break the pattern in someone’s scroll. 

Here’s how I stopped staring blankly into the camera – and said something people may care about. 

Before we start shooting, here’s a quick reminder why we’re even having this conversation. 

Videos work – for two very good reasons: 

So no, it’s not just about chasing trends. 

Videos are strategic. They carry an outsized impact, especially for those offering high-trust service in a noisy space. 

Now, let’s get to what you need to actually say. 

The first five seconds of your video matter more than anything else. You need to earn the right to keep someone watching. 

This means don’t start with “Hey everyone!” or “Just wanted to hop on and share…”  

We’re not influencers making videos on YouTube or Instagram. 

Instead, lead with something like: 

The goal isn’t to be viral. 

You only need to stop the scroll and make someone feel like they want to hear the rest of your point. 

This is where most videos fall apart: they try to say too much. 

You don’t need to give a TED Talk. 

Instead: one video = one useful idea. 

Here are a few examples that work well for us: 

Pick one. Say it like you would to a smart client or colleague. 

You don’t need to say “Like and follow for more tips.” You’re not selling leggings. 

But it does help to end with a soft prompt that invites connection or keeps the conversation going.

Try things like: 

The goal isn’t engagement for its own sake. 

It’s to make it easy for the right people to see themselves in your thinking—and maybe send a message later. 

If you want to record a few videos this week but don’t know where to start, try one of these: 

Each of these gives you a tight focus, a relevant message, and a chance to show your voice—without needing a script. 

You don’t need a script. You don’t need a teleprompter. You don’t need a perfect one-take. 

Just say something useful. Say it like you’d say it to a smart peer. 

LinkedIn is full of polished nonsense. 

Go check out mine – they are far from perfect. 

But a 90-second video of a real person saying something thoughtful in plain English? That stands out. 

So talk to the camera like it’s someone who already respects you. 

Because odds are, that’s who’s watching.

🚨 Chart crimes 

WTAF.

Remember, the path to success is paved with continuous learning and embracing fresh perspectives.

Let's stay connected, share ideas, and elevate your consulting business.

Stay curious, friends.

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