Chocolatey Community Coffee Break

Join the Chocolatey Team on our regular monthly stream where we discuss all things Community, what we do, how you can get involved and answer your Chocolatey questions.

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Chocolatey Product Spotlight

Join the Chocolatey Team on our regular monthly stream where we put a spotlight on the most recent Chocolatey product releases. You'll have a chance to have your questions answered in a live Ask Me Anything format.

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Announcing Chocolatey Central Management 0.10.0

Livestream from
Thursday, 06 October 2022

We recently released our largest update to Chocolatey Central Management so far. Join Gary and Steph to find out more about Chocolatey Central Management and the new features and fixes we've added to this release.

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Chocolatey and Intune Overview

Webinar Replay from
Wednesday, 30 March 2022

At Chocolatey Software we strive for simple, and teaching others. Let us teach you just how simple it could be to keep your 3rd party applications updated across your devices, all with Intune!

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Chocolatey For Business. In Azure. In One Click.

Livestream from
Thursday, 9 June 2022

Join James and Josh to show you how you can get the Chocolatey For Business recommended infrastructure and workflow, created, in Azure, in around 20 minutes.

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The Future of Chocolatey CLI

Livestream from
Thursday, 04 August 2022

Join Paul and Gary to hear more about the plans for the Chocolatey CLI in the not so distant future. We'll talk about some cool new features, long term asks from Customers and Community and how you can get involved!

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Hacktoberfest Tuesdays 2022

Livestreams from
October 2022

For Hacktoberfest, Chocolatey ran a livestream every Tuesday! Re-watch Cory, James, Gary, and Rain as they share knowledge on how to contribute to open-source projects such as Chocolatey CLI.

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Chocolatey Product Spotlight: Chocolatey 1.2.0 and Chocolatey Licensed Extension 5.0.0

Livestream from
Thursday, 03 November 2022

Join Paul and Gary for this months Chocolatey product livestream where we look at the latest release of Chocolatey 1.2.0, Chocolatey Licensed Extension 5.0.0 and shine a spotlight on the new hook scripts functionality. This opens up so many possibilities for Chocolatey CLI users!

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Chocolatey Coding Livestream

Livestream from
Tuesday, 29 November 2022

Join Josh as he adds the ability to manage Chocolatey GUI config and features with the Chocolatey Ansible Collection.

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Introduction into Chocolatey with Veeam

Webinar from
Tuesday, 13 December 2022

Join Gary, Paul, and Maurice as they introduce and demonstrate how to use Chocolatey! Questions will be answered live in an Ask Me Anything format.

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Chocolatey Software

The Sane Way to Manage Software on Windows

Chocolatey Software

The Sane Way to Manage Software on Windows

Our Values and Approach

Chocolatey is focused on helping our community, customers, and partners with solutions that help fill the gaps that are often ignored. We offer a simple, pragmatic, and open approach to software management on Windows.

What is Chocolatey
The biggest challenge is reducing duplication of effort, so users turn to Chocolatey for simplicity.

Rob Reynolds, Founder of Chocolatey Software

Chocolatey for Business

Making It Easy

Chocolatey was created by Rob Reynolds in 2011 with the simple goal of offering a universal package manager for Windows. Chocolatey is an open source project that provides developers and admins alike a better way to manage Windows software.

With more versions of software to support and endless updates, our goal was to help our customers become efficient and innovative software-driven organizations.

Chocolatey Software was established in 2016 as a way to ensure the longevity of our offerings. We launched Chocolatey for Business (C4B) the same year that is Complete Software Management, built on top of our popular open source offering. C4B is focused on three value-added areas - improved security, enhanced productivity features, and enabling more visibility. C4B is also backed with dedicated support, services, and roadmap.

Meet the Team

Tyler Abegg
Tyler Abegg

Account Manager

Paul Broadwith
Paul Broadwith

Technical Engineering Manager
Rain Sallow
Rain Sallow

Software Engineer
Stephanie Hays
Stephanie Hays

Senior Software Engineer
Josh King
Josh King

Infrastructure Operations Engineer
Cory Knox
Cory Knox

Junior Software Engineer
Kim Nordmo
Kim Nordmo

Software Engineer
Gary Ewan Park
Gary Ewan Park

Principal Software Engineer
Brandi Reynolds
Brandi Reynolds

HR & Finance Manager

Rob Reynolds
Rob Reynolds

CEO, Founder

Ryan Richter
Ryan Richter

Support Engineer
James Ruskin
James Ruskin

Senior Solutions Engineer
Scott Sader
Scott Sader

Chief Information Security Officer
Jessica Sheldon
Jessica Sheldon

HR Administrator

Stephen Validinger
Stephen Validinger

Support Manager
Chris White
Chris White

Junior Support Engineer