Ryan Sheehan

Inspirer
DISC Type : di

Fractional CTO at Greenlight Advisors

Dallas-Fort Worth Metroplex, United States

Overview

Ryan Sheehan is a Fractional CTO with over 18 years of experience, specializing in modernizing software for government and public sector organizations. His expertise spans cloud transformation, UX systems, and scaling engineering teams. A recent Executive MBA graduate from Southern Methodist University, he is also an AWS Certified Cloud Practitioner.

Outside of his technical leadership, Ryan is driven by a mission to make technology impactful for public services. He demonstrates a strong sense of community and empathy, and colleagues have highlighted his supportive nature and "CAN DO" mindset when helping team members succeed.

Unique fact: Ryan directed a UX design system that successfully scaled from just 5 to over 100 applications, unifying brand consistency.

Personality Overview

Generous

Fast Adopter

Achievment Oriented

They measure a product on its merit but can be influenced by strong testimonials.  They usually prefer to drive the conversation. They respond well to objective pitches but also attach some value to relationships.

Topics They Care About

GovTech Modernization
His entire career mission is focused on making technology accessible and impactful for government and public sector organizations.
UX Design Systems
He has a proven track record of scaling large-scale UX systems, having expanded one from 5 to over 100 applications at Tyler Technologies.
Cloud Transformation
This is a core part of his professional focus, further validated by his recent AWS Certified Cloud Practitioner certification.

Media Appearances

Ryan has no verified media appearances

Work History

10-2025
Fractional CTO at Greenlight Advisors
10-2025
Founder at Prosper CTO
1-2020
Software Development Manager at Tyler Technologies
1-2016 - 1-2020
Engineering Team Lead at Tyler Technologies
6-2013 - 1-2016
Senior Software Engineer at Tyler Technologies

Education

8-2022 - 5-2024
Executive MBA from Southern Methodist University
2006 - 2008
Graduate Certificate from Southern Methodist University

More Information

Social Presence :

Prographics :

Exp : 18 Location : Dallas-Fort Worth Metroplex, United States Job Level : Leadership Designation : Fractional CTO at Greenlight Advisors
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Insights For Selling To Ryan

During A Call Or A Meeting

DO's

  • Keep your pitch focused on the impact but insert some anecdotes into it
  • Refer to testimonials from well known people to highlight the value of your product
  • Get them to a point where they are ready to bat for your product internally

DONT's

  • Don’t be too verbose or overly friendly; a little bit, however, is fine
  • Avoid focusing only on the product or its ROI, keep building trust subtly
  • Don't be unorganized, be prepared for the pitch

When Cold Calling

When Writing An Email

While Negotiating & Closing

    The secret to closing fast with Ryan is

  • Belief in the value of the product, relationship and a sense of accomplishment matter the most.
  • Will you ever get a clear answer from Ryan

  • They are not shy of saying no if they do not develop trust in your product.

Insights For Deal Planning

    How fast (or slow) will Ryan move?

  • They can take fast decisions if they develop conviction in the product and find you trustworthy.
  • Can Ryan take some risk or not?

  • They have the capability of taking risky decisions if necessary.

You And Ryan

Personality Compatibility


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