SESSION 4
The Multi-Business Executive - Scaling Leadership Through Fractional Infrastructure
Author
Building The 'Fractional Dream Team' and Scaling Leadership Across Multiple Businesses
How does a single leader scale their financial expertise across multiple companies? The answer, as we learned in a recent session at “The Future is Fractional,” is by building a “fractional infrastructure.”
In this insightful session, Scrubbed’s Arian David was joined by Ottavio Siani, a fractional CFO and the owner of Triangle Coffee. Ottavio lives this model from two perspectives: as a business owner who uses fractional services (including Scrubbed) and as a fractional CFO who builds financial teams for his clients.
He shared his playbook for designing scalable financial systems, which all starts with what he calls the “fractional dream team.”
Here are the key highlights from their conversation.
The "Fractional Dream Team" Model
When Ottavio engages with a new client, he doesn’t just offer his own services. He presents a “full solution” to their entire finance problem. This solution, his “Dream Team,” consists of three key parts:
The Fractional CFO (Himself):
The high-level strategist, relationship manager, and leader who designs the systems.
The External Execution Team (Scrubbed):
The reliable, expert team that handles the core bookkeeping and accounting
The Internal Coordinator:
A full-time employee at the client’s company who acts as the reliable, trustworthy bridge between operations and the finance team.
“In about 75% of my engagements,” Ottavio explained, “they’re also deciding to work with Scrubbed, so that they can get not just my work, but this full team.”
Creating a Self-Sustaining System
Ottavio’s primary goal is to create a finance function that can operate independently. His process is simple and effective:
BUILD
Ottavio’s primary goal is to create a finance function that can operate independently. His process is simple and effective:
DELEGATE
In the following months, he is “less hands-on,” training the internal coordinator to take a “first pass” at the analysis.
SCALE
As the core processes become self-sustaining, he steps back.
The ultimate goal, he says, is to transfer ownership. “That’s often what I’m selling my clients,” Ottavio shared. “I will build this… set of processes, I will train the people necessary to do them, and then when I’m at the end of the scope… you, the company, will own this.”
Earning Board and Auditor Buy-In
Ottavio often enters companies where the founders are “product people,” not finance people, and are disconnected from their financial information.
His model works by building trust in the data. His goal is to “Take the way that they think about the business, and connect it to the presentation of their financial information.”
This leads to a key leadership lesson: focus on the fundamentals first.
Ottavio explained that he often has to “manage up” and tell a CEO they can’t work on a “really interesting question” until the basic data, like an accounts receivable aging report, is accurate. Oftentimes, he noted, complex, one-off analyses are only needed because the leadership can’t trust the rest of their financial information. Once you build a great process with accurate data, many of those complicated questions fall away.
The key, he concluded, is
making sure that you are doing the simple things, but doing them really, really well.”
Ottavio Siani
Fractional CFO and Founder
Why Reliability Is Worth Paying For
When clients ask why they should use his recommended team versus a cheaper alternative, Ottavio’s answer isn’t about cost, it’s about reliability.
He noted that he often enters companies that have already worked with third-party bookkeepers, and is often skeptical of it because it hasn’t worked out for them.
“You really want to get… what you’re promised on time, and you need it to be accurate,” he stressed.
He also highlighted the value of Scrubbed’s scale. He explained that if his team encounters a complex or niche accounting issue, they can tap into the collective expertise of Scrubbed’s larger organization. This internal “knowledge base” means there is almost always an expert who has handled a similar situation and can provide the necessary guidance, a resource he described as “enormously helpful.”
Watch the Full Session
Ivan’s story is a masterclass in how to strategically leverage fractional talent to not only manage growth but also to build a more resilient and efficient operation.
To get all the insights, including Ivan’s advice on the single best role to start with and his hindsight on what he would do differently, you can watch the full session recording.
