Vertical Jump AI 路 About

Same playbook. Smaller scale. Faster results.

Most SMB leaders aren’t asking whether AI works. They’re asking how AI improves their business, which tools actually deliver, and who stays accountable when something doesn’t.

John Esposito

Founder & Practitioner
5660 Strand Ct.
Naples, FL 34110

Our Mission

To make AI a real advantage for small businesses, through industry-focused best practices and local accountability

What We Stand For

Four commitments we make to every client.

Measurable ROI First

Every engagement starts with a clear ROI model. If we can't show you where the return comes from, we don't start.

Implementation, Not Advisory

We do the hands-on work: solution selection, configuration, training, and go-live. One team, accountable from start to finish.

Local Accountability

We're based in Naples and stay engaged beyond go-live. Monthly reviews, performance tracking, and ongoing optimization keep your outcomes improving.

Industry-Focused, Not Generalist

Five verticals: restaurants, medical practices, real estate, legal and accounting, and home services. Each engagement matched to the work, whether a vetted platform, an AI workflow, or team enablement.

Enterprise-grade discipline. Measurable outcomes.
One number to call.

About Me

I spent 20 years in enterprise software, including 16 years at Salesforce where I progressed to Professional Services Executive. I’ve also held leadership roles at high-growth startups including Vlocity (Salesforce Industries) and Radius Intelligence. I’ve delivered hundreds of implementations, with deep focus on regulated industries such as healthcare and financial services. The accountability is the same on every engagement: aligning on outcomes, delivery, adoption, and improvement that compounds over time. I’m building Vertical Jump AI to bring that discipline to small businesses in Southwest Florida

Salesforce logo

Leading Business Transformation

  • 20 years driving global implementations
  • Adoption and outcomes leadership
  • Regulated industries: healthcare and financial services
Marist University logo

Marist University

  • MS Computer Science
  • BS Accounting
MIT logo

MIT Professional Education

  • Applied Agentic AI for Organizational Transformation
  • No Code AI and Machine Learning

Ready to Jump Ahead?

Map Your AI Opportunities.
Know exactly where to start.

A structured 30-minute conversation to identify where AI pays back fastest in your business, and a clear, prioritized plan to get there.

No pitch  路  No pressure  路  30 minutes