Stephen Gregorio

Trailblazer
DISC Type : ID

Advisor at Intelligent DataWorks

Naples, Florida, United States

Overview

Stephen Gregorio is a seasoned, operationally-focused CFO and CPA with over 30 years of experience in the high-tech sector. He specializes in scaling companies through IPOs, M&A transactions, and significant capital fundraising, having managed finance, legal, HR, and IT teams. He is an alumnus of Bentley University.

Outside of his direct financial roles, Stephen serves as an advisor and board member for multiple technology ventures. His public commentary shows a keen interest in the advancement of cutting-edge technologies like AI-driven weather forecasting and SaaS-based supply chain platforms, highlighting progress made by teams in these fields.

He played an instrumental role in the successful $565M sale of Black Duck Software to Synopsys.

Personality Overview

Friendly But Fast

Values Relationships

Assertive

They are not against taking risks and can make tough decisions when required.
  A combination of speed and relationship gets the best response from them. They are more likely to accept new and exciting technologies.

Topics They Care About

High-Tech Finance
As a multi-time CFO for tech companies, he has deep experience in fundraising, M&A, and navigating a company through an IPO.
SaaS B2B Platforms
Serves on the board of Fairmarkit, a VC-backed, AI-based SaaS platform focused on optimizing supply chain tail spend for enterprises.
AI Applications
He is an advisor at Intelligent DataWorks, an AI-driven business, and has publicly praised the progress of AI-powered weather forecasting systems.

Media Appearances

Stephen has no verified media appearances

Work History

5-2025
Advisor at Intelligent DataWorks
2-2025
Fractional CFO at Metrika
11-2024
Financial Advisor at TalkingHeads Wireless
9-2024
Board Member at FeedbackNow
3-2018
Board Member at Fairmarkit

Education

1978 - 1982
BS from Bentley University

More Information

Social Presence :

Prographics :

Exp : 7 Location : Naples, Florida, United States Job Level : Leadership Designation : Advisor at Intelligent DataWorks
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Insights For Selling To Stephen

During A Call Or A Meeting

DO's

  • Give them control of the sales process
  • Use phrases like ‘your decision will’, ‘you will impact’ etc.
  • Help them visualize the impact of their decision

DONT's

  • Don’t hesitate from asking them how they truly feel about your product
  • Don't make any commitments that you might not be able to fulfill
  • Don’t hesitate from asking questions or pushing them, but take a friendly approach

When Cold Calling

When Writing An Email

While Negotiating & Closing

    The secret to closing fast with Stephen is

  • Relationship and product conviction matter equally, followed by a sense of achievement.
  • Will you ever get a clear answer from Stephen

  • If they are not convinced, they will say no though in a friendly way.

Insights For Deal Planning

    How fast (or slow) will Stephen move?

  • They can make decisions quickly if they develop trust in you and conviction in the product.
  • Can Stephen take some risk or not?

  • If necessary, they will be ready to take risks.

You And Stephen

Personality Compatibility


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