Jess Bellissimo

Executive Operator

Building Operating Systems for Growing Businesses


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About

Background

19+ years building and scaling service businesses in legal tech, logistics, and disaster restoration. Former CEO and COO. Scaled to $45M in annual revenue, operating across North America, Europe and Asia. Sold to private equity-backed competitor.

What I'm good at: Building company operating systems/infrastructure that scale. I love Moneyball—break the business into its most basic formula, display it on public dashboards with clear owners and expectations.

  • Sales & customer service playbooks
  • Service delivery workflows
  • Optimal department structures
  • Job descriptions → scorecards with clear deliverables
  • KPI dashboards everyone can see
  • Red teaming/stress testing organizations
  • Bringing technology to unsexy processes

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.

Building an AI diagnostic system for CEOs — helps operators rapidly understand their business and identify highest-leverage improvements. Testing with fractional CFO practice. Shipping in 7 days.

I learn by building: research, prototype, build, seek feedback, iterate brutally honestly.

Current Project

AI CEO Advisor — Diagnostic system that helps CEOs rapidly understand their business using proven frameworks. Upload financials, answer structured questions, get prioritized action plan.

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

See all projects →

What I'm Learning

Technical
  • Prompt engineering & AI workflows
  • Python, Streamlit, data pipelines
  • Rapid prototyping with Bolt.new, Lovable.ai, Cursor
  • GitHub, version control, deployment
Process
  • Building in public
  • Ship fast, learn faster
  • Validating ideas with real data
  • AI-assisted development workflows

What I'm Looking For

Open to co-working on projects and solving real problems with great teams.

I'm obsessed with the idea of people going "founder mode" on their own problems—like someone with a rare disease who seeks to "dent the universe" by building the right team to improve outcomes for themselves and others.

Roles where operational experience + AI fluency + bias toward action matter:

  • Solutions Engineering
  • Product Operations
  • Strategic Initiatives

Particularly interested in companies building foundational AI tools.