Ryan Reading

Observer
DISC Type : ic

SVP, Software Engineering at Skydio

San Francisco, California, United States

Overview

Ryan Reading is the SVP of Software Engineering at Skydio, where he leads the development of connected, autonomous drone fleets for public safety, defense, and energy. Previously at Samsara, he scaled the software team from 25 to over 200 during a period of hypergrowth. He holds a Bachelor of Science from Missouri University of Science and Technology.

He holds multiple patents, including one for an innovative "Event notification system" and another for a "Baseline event detection system".

Personality Overview

Assertive

Example Seeker

Value Driven

They are generally strong communicators and are not easy to convince.  They often ask many questions and rely heavily on information and documentation. They can sound friendly and charming but can quickly change gears to become inquisitive and probing.

Topics They Care About

Autonomous Drones
Passionate about building drones as infrastructure to solve real-world problems for critical industries like public safety, defense, and energy utilities.
Engineering Leadership
Experienced in scaling software teams through hypergrowth, having grown an engineering organization from approximately 25 to over 200 people at his previous company.
AI in Fleet Safety
Led the product and engineering for AI dashcam safety features at Samsara, such as tailgating and distracted driving detection, to improve fleet safety.

Media Appearances

Ryan has no verified media appearances

Work History

6-2025
SVP, Software Engineering at Skydio
10-2020 - 8-2025
VP, Software at Skydio
11-2019 - 6-2020
VP/GM - Fleet Safety at Samsara
10-2018 - 11-2019
VP of Engineering at Samsara
7-2017 - 9-2018
Senior Director Of Engineering at Samsara

Education

1997 - 2002
Bachelor of Science - BS from Missouri University of Science and Technology

More Information

Social Presence :

Prographics :

Exp : 23 Location : San Francisco, California, United States Job Level : Leadership Designation : SVP, Software Engineering at Skydio
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Insights For Selling To Ryan

During A Call Or A Meeting

DO's

  • Invite them for a social do but don’t rely solely on the relationship
  • Help them realize that there is no personal risk in making this decision
  • Share testimonials from known people and give multiple examples of product value

DONT's

  • Don’t try to rush them into a decision, provide all necessary information first
  • Don’t brush off any concerns, take all questions seriously
  • Don’t rely excessively on your relationship with them to win the deal

When Cold Calling

When Writing An Email

While Negotiating & Closing

    The secret to closing fast with Ryan is

  • Clear proof of product value matters to them, followed by others' testimonials and rapport.
  • Will you ever get a clear answer from Ryan

  • They are practical yet friendly, don’t expect a clear no very often.

Insights For Deal Planning

    How fast (or slow) will Ryan move?

  • They like to analyze well and then make their decisions.
  • Can Ryan take some risk or not?

  • They systematically evaluate all decisions and are unlikely to take many risks.

You And Ryan

Personality Compatibility


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