5 Winning Strategies for Fractional CMOs From an Agency Exec
Marketing Executive Matt DiPaola on brand vs performance marketing, the 30-60-90 playbook, AI tools for marketers, and treating your career like a portfolio.
June 8th, 2026
Matt DiPaola has spent 30 years in the marketing trenches, from convincing people to sign up for free Hotmail accounts to launching Disney projects on Fortnite. He's worked at Leo Burnett, BBDO, DDB, Critical Mass, and Huge, across clients like Netflix, Google, and Four Seasons.
Recently, he joined BIMM as a SVP, Marketing & Innovation. When he gave this interview, he was focused on managing his own practice as a fractional CMO and growth consultant working for businesses in a range of industries.
We sat down with him to get his take on building a fractional portfolio, navigating the AI landscape, and what it actually looks like to lead marketing from the outside in.
1. Build Brands Through Behavior, Not Just Design
Most people think branding starts with visuals: logos, colors, websites, taglines. But strong brand identities go much deeper than aesthetics. There are really three layers to establishing a brand:
- How you look in the world
- What you stand for in the world
- How you behave with employees and customers
"That behavior piece is massive," he said, "especially as you get bigger, because it gets inconsistent if you're not maintaining it properly."
DiPaola's proudest example of strengthening brand behavior comes from his fractional work with Forest Carbon, a forest restoration company in Indonesia. Since the carbon credit market is crowded and controversial---everyone uses the color green and claims their credits are the best---Forest Carbon took a completely different direction.
They discovered that when a forest comes back to life, you can hear it: the wildlife returns and the soundscape changes. So DiPaola helped them build a vibrant, optimistic brand around the science of listening to the forest, turning animal sounds into their visual and sonic identity.
The result? Their chief revenue officer started closing deals faster because the brand was so recognizable. And the sonic branding became integrated into how the company actually measures and operates, not just how it markets.
2. Stop Choosing Between Brand vs. Performance Marketing
The brand vs. performance debate is futile. The best marketers know how to shift between the two depending on the company's stage, goals, and growth constraints.
"There are brand companies who don't look at ROI at all and there are performance companies that don't look at brand [marketing] at all," DiPaola said. "You need to understand as a marketer where that organization is in its journey."
Early-stage companies, for example, often need performance marketing to prove traction and drive measurable growth quickly. But eventually, many businesses hit a ceiling where performance optimization alone stops working. That's when brand marketing becomes the growth lever---helping companies build trust, differentiate in crowded markets, and win larger opportunities.
DiPaola points to Forest Carbon again: They focused on performance marketing up to a certain point, but recognized they needed a premium brand to land the Microsofts and luxury brands willing to spend millions on carbon credits. Fractional CMOs who diagnose where a company is in their marketing journey and adjust strategy accordingly will stand out.
3. Use Your First 30 days to Listen, Not Lead
DiPaola follows a 30-60-90 framework, and those first 30 days are all about absorbing information before taking action.
"The first 30 days is a listening tour," he said. "If you come in with a preconceived playbook, you're just going to miss the nuances."
Meet department leaders, understand company goals, analyze competitors, review customer data, and identify operational gaps. Only after gathering that context does strategy development begin.
In fact, DiPaola recommends following a clear sequence for that first month:
- Step one: Understand the business, not just the brand, including goals, board expectations, and three-year plans.
- Step two: Deep dive into the customer, including what problems they're solving, unmet needs, and white space.
- Step three: Unpack the data; see what's worked, what hasn't, and where the gaps are.
Then, you can spend days 30--60 turning all those inputs into a go-to-market plan. The final stretch is establishing feedback loops, board buy-in, and budget approvals. By day 90, the team and budgets are in place and you're ready to execute.
Check out our Fractional Playbook for more actionable tips on running a fractional business.
4. Treat Your Fractional Career Like an Investment Portfolio
Fractional work gives experienced marketers something many traditional executive roles can't: variety. Instead of being tied to one company or industry, fractional leaders can apply their expertise across multiple businesses, markets, and growth stages. Just look at DiPaola, whose portfolio included climate tech businesses, Fortnite, a plumbing company, a Coachella agency, and musicians moving into tech.
Still, DiPaola knows the fractional model does more than just offer range; it helps manage risk. Just like investors are told to diversify assets, fractional professionals should diversify income streams. Some clients are fee-for-service, some are set up with retainers, and some offer equity.
The best part? While he's diversifying, he's also making his own schedule. There's no expectation to sit at a desk from nine to five. Some days, he works a few hours. Some nights, he reviews pitch decks at 11:00 PM. The point is, he chooses.
5. Stop Reading About AI Tools and Start Using Them
Matt has a go-to analogy for those struggling to adopt AI tools: Some marketers are house cats and some are alley cats. House cats read the online chatter and regurgitate opinions. Alley cats are out in the world trying new tools and forming their own viewpoints. Needless to say, marketers have to be alley cats right now.
"As a marketer, you have to be hands-on, you have to be using the tools, and you have to have an active perspective," he said.
Rather than waiting for a perfect roadmap, jump in to actively test platforms and emerging use cases to understand where AI genuinely moves the needle. DiPaola, for example, has been hands-on with ChatGPT, Jasper (especially for brand voice work), and Google Gemini for videos and images. He's watching the agentic AI space closely and is fascinated by the concept of digital twinning: consultants and VCs creating AI versions of themselves that can do first-round pitch reviews or consulting work.
The marketers who dive in and get their hands dirty will be the ones who identify real opportunities before everyone else catches up.
Grow Your Fractional Marketing Career
Ready to build a flexible career as a fractional marketer? Go Fractional provides the tools and resources to help. Apply to become a member, build your professional profile, and connect with companies looking for experienced marketing talent.
You can also explore the Fractional Job Board---updated daily---for the latest high-impact fractional, interim, and contract-to-hire roles across marketing, operations, tech, and more.
