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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Working at Chocolatey Software

Search All Open Positions

Be at Your Best

If you are looking for the next move, or just want to be part of an exciting and fun business where you can be challenged, accepted, and supported then Chocolatey is a place where you can make your mark.

We are growing fast and encourage everyone at Chocolatey Software to have a real impact on the company and our customers every day. We are driven, focused, and encourage creativity and collaboration.

Work local and think global. We have created a remote friendly working culture. With the latest technology we allow our team to work anywhere in the world, still feel connected, and get their work done.

We have developed our culture to offer a real work and life balance. Offering a comprehensive benefits package and option to work where you can be at your best.

Learn and Grow with Chocolatey

Bring New Ideas Forward

Chocolatey Software

Interact with Customers

Help Customers and Community

Chocolatey Software is leading the way in how organizations can successfully automate their Windows environments. Chocolatey is a proven software management solution for Windows - hundreds of thousands of users and thousands of organizations, including Microsoft, look at Chocolatey as a solution for rapid deployment and management of software on all supported Windows platforms, including Docker containers and cloud environments.

If you like to help customers, bring new ideas forward, and want to learn and grow then Chocolatey offers you an excellent platform.

Be Part of The Change

We often hear how system engineers can spend hours deploying and configuring Windows software manually. Traditional tools are not built for modern automation and gaining insights and consistency across IT environments is not always easy. Chocolatey for Business (C4B) has helped hundreds of system admins save time, reduce downtime, and accelerate deployments. Chocolatey helps organizations bridge the gap from current approaches to proven DevOps approaches.

If you are excited about how automation and software is changing the world then Chocolatey could be the right place for you to drive that change, develop new skills, and make great connections.

Search All Open Positions
The Future of Windows Automation

"The Future of Windows Automation"

with Rob Reynolds, Founder of Chocolatey Software