Josh Quagliaroli

Observer
DISC Type : ic

Chief Strategy Officer at agile six

New Haven, Connecticut, United States

Overview

Josh Quagliaroli is a multi-faceted executive at Agile Six, having held Chief Officer roles in Strategy, Delivery, and Growth. With a background at the Department of Veterans Affairs and certifications like SAFe, he leads with a non-traditional, people-first approach to government contracting, focused on purposeful work.

Outside of his executive roles, Josh is a self-described introvert who enjoys a quiet home life in Connecticut with his wife and pets. His hobbies include gardening, playing video games, and watching anime. He prioritizes spending quality time with his family.

He previously worked at the US Digital Service, which was based at the Department of Veterans Affairs.

Personality Overview

Curious

Assertive

Example Seeker

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. They are generally strong communicators and are not easy to convince.

Topics They Care About

Purpose-Driven Growth
Champions a non-traditional business development mindset focused on purposeful work and a people-first culture, rather than a traditional sales approach.
Veterans' Digital Experience
Has a deep background with the Department of Veterans Affairs and is passionate about improving how veterans access services and information through platforms like VA. gov.
Self-Management Models
Advocates for organizational structures that balance autonomy and accountability, avoiding traditional management layers to empower teams.

Media Appearances

Sixer Spotlight with Josh Quagliaroli. Featured in Agile Six

See Now

Work History

9-2025
Chief Strategy Officer at agile six
2-2024 - 10-2025
Chief Delivery Officer at agile six
2-2023 - 3-2024
Chief Growth Officer at agile six
7-2019 - 2-2023
VP of Strategy at agile six
4-2018 - 7-2019
Director of Strategic Operations at agile six

Education

MA from University of Nottingham
BA from Roger Williams University

More Information

Social Presence :

Prographics :

Exp : 15 Location : New Haven, Connecticut, United States Job Level : Leadership Designation : Chief Strategy Officer at agile six
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Insights For Selling To Josh

During A Call Or A Meeting

DO's

  • Use phrases like ‘clear proof that’, ‘data shows’ etc.
  • Help them realize that there is no personal risk in making this decision
  • Invite them for a social do but don’t rely solely on the relationship

DONT's

  • Don’t be too objective but make sure to pad your storytelling with data points
  • Don’t rely excessively on your relationship with them to win the deal
  • Don’t brush off any concerns, take all questions seriously

When Cold Calling

When Writing An Email

While Negotiating & Closing

    The secret to closing fast with Josh is

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

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

Insights For Deal Planning

    How fast (or slow) will Josh move?

  • They like to analyze well and can take their time to reach any decisions.
  • Can Josh take some risk or not?

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

You And Josh

Personality Compatibility


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