Jess Bellissimo

How I Operate

Most operational problems exist because leaders don't fully understand their own business.

My approach: Understand the system before trying to fix it.

• Map the stakeholders — who needs what, where interests align and conflict
• Identify headwinds and tailwinds — what's working for you, what's working against you
• Understand how you make money — unit economics, margins, cash flow
• Find the constraint — where does growth stall? where does the system break?
• Prioritize leverage — what matters most, what can wait, what's distraction
• Execute with accountability — clear owners, clear metrics, clear consequences

Built this way at multiple companies through $45M+ in revenue and PE exits.

Now I'm building tools that help other operators do the same thing.

Current Focus

Using AI to scale operational expertise

The bottleneck in most growing businesses isn't strategy — it's operational execution. Most operators know what to do but lack the systems and capacity to do it consistently.

I'm building tools that:

• Help operators rapidly diagnose their business (what's actually broken vs. what feels broken)
• Automate routine operational work (data extraction, report generation, process monitoring)
• Surface the right information at the right time (forward-looking metrics, not just rearview)

The goal: Make sophisticated operational capability available to businesses that can't afford a full-time COO.