Jess Bellissimo

Executive Operator

Learning AI by Building


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About

The 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 with global presence.

In 2020, COVID hit hard—reducing revenue by 25%. Throughout the second half of 2020, we rebuilt the business to be more digital, remote-compliant, and resilient. In 2021, we had our best year in both revenue and profit—all without any layoffs.

Exited to PE-backed strategic acquirer.

What I'm good at: Building company operating systems 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

Government should work in service of citizens and businesses. Understand what people want, deliver those outcomes. Let AI handle the 95% routine work, humans focus on high-attention 5% scenarios.

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

The Projects

Each project: 2-4 working sessions over 1-2 days. Then iterate and solicit feedback, always aiming to be brutally honest about what works.

h/t Matthew McConaughey on the "Greenlights" name—I enjoy consulting, but it's more fulfilling to own the outcome.

See detailed project breakdowns →

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.