Behind the Scenes of a Fractional Executive’s Journey
Based in Toronto, Theo Hildyard is a Fractional CMO working with B2B tech companies, particularly VC-backed early-stage startups and PE-backed mid-sized businesses. He partners with organizations undergoing marketing transformation or turnaround, helping them accelerate growth and scale effectively.
“A Fractional CMO focused on small-medium sized tech companies undergoing marketing transformation / turnaround. I specialize in Private Equity PortCos needing to accelerate change and VC backed startups needing to scale.”
The Leap Into Fractional Leadership: Theo's Career Pivot
The move into Fractional work was driven by a desire for greater control.
“Desire for more control over who I work with, where and when”
That shift allowed him to choose the companies he partners with and the way he delivers impact, aligning his work with both his expertise and preferred way of operating.
Today, he works closely with B2B Tech companies, especially VC backed early stage and PE backed mid-size businesses, helping them navigate growth, change, and scale.
Superpower in Action: Theo's Strength as a Fractional Executive
Every Fractional brings a unique strength. His superpower is clarity at the foundation of go-to-market strategy.
“Getting the upfront GTM story & strategy as crisp as possible so when we deploy AI or agencies (more likely AI) it has rock solid base to work with.”
His approach ensures that execution, whether through AI or agencies, is built on a strong strategic core that drives results.
Breaking the Myths: What Fractional Leadership Really Looks Like
“You dont need a Fractional CMO to create PowerPoint. A fraction CMO can create great decks of course. But if that is all you need, CMO with 20 years experience will likely not be good value for money”
The value lies far beyond presentations, it’s about delivering high-level strategic impact where it matters most.
Wins That Define Their Fractional Journey
Theo’s work has delivered measurable growth for clients.
“Fractional GTM Strategy and hands-on GTM operational support (sitting cross-functionally between sales and marketing) for Mid-Sized mature SaaS company. YoY new business pipe growth of 190%, ASP growth of 53% and deal volume growth of 82%”
These outcomes highlight his ability to drive both strategic and operational success across organizations.
Like any Fractional career, results come from consistency, focus, and execution across multiple fronts.
Lessons from the First Few Months in Fractional Work
Looking back, Theo reflects on one key reality when starting out.
Theo's Advice for New Fractionals
“Business Development takes a lot longer than you expect. As in double your expectation and it still takes even longer!”
He also emphasizes a practical approach to pipeline building.
“As with the companies you service, your win rate is likely to be in the 20% range. So make sure you have 5 clients in the pipe for every 1 you close.”
Beyond the Resume: The Real Theo
Outside of work, he has been self-teaching the guitar. What started as a difficult pursuit became more enjoyable after redefining the goal.
“Self teaching the guitar. Was very painful for long time while my goal was to "be a musician". Then I had the realization what I actually want to do is play Wish You Were Here and Hotel California etc and look cool doing it. Things because a lot more fun after that.”
That shift in mindset reflects a broader philosophy he brings into his work and life.
One Quote That Sums It All Up
“B2B marketing has moved on. MQLs exist but are not "the way". Brand/Comms is “the way” so we influence people (and LLMs) long before they click. I love to work with people who truly understand this (as opposed to those who need convincing of it)”
This perspective captures his view on modern B2B marketing and where true impact is created.
