In this special anniversary episode, we celebrate a major milestone: 25 years of Community IT. Founded on February 1, 2001, by David Deal as a mission-focused spin-out from Reliacom, Community IT has spent a quarter-century navigating the ever-changing tides of technology for nonprofits exclusively. CEO Johan Hammerstrom, who was one of the early employees to move from Reliacom to the new company, joins us to reflect on our journey from the early days of wiring offices for the internet to our modern role as a national provider of remote IT services and cybersecurity.

We discuss how our bedrock foundation of servant-leadership has allowed us to remain a stable, trusted partner for the nonprofit community through dot-com busts, financial crises, and global shifts in how we work.

Beyond the history of servers and software, this conversation focuses on the vibrant people who make our mission possible. Johan shares why it is useless to predict exactly where IT will be in five years, and why Community IT instead invests in the creative, dedicated staff who can guide nonprofits through whatever the future holds.

Whether you have been a partner since our founding or are just joining our community, tune in to hear how our commitment to technology expertise ensures that nonprofits can stay focused on their missions, no matter how the digital landscape evolves.

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Start a conversation :)

• Register to attend a webinar in real time, and find all past transcripts at https://communityit.com/webinars/
• email Carolyn at cwoodard@communityit.com
• on LinkedIn

Thanks for listening.

To follow on from our recent discussions regarding the rapid adoption of artificial intelligence in the nonprofit sector, this episode explores the critical technical and privacy distinctions between public and enterprise AI tools.

The CISA Incident and the AI Privacy Gap

Last week, news outlets including Politico reported that the interim director of the Cybersecurity and Infrastructure Security Agency (CISA), Madhu Gottumukkala, mistakenly uploaded sensitive government contracting documents into a public version of ChatGPT. This triggered automated security warnings designed to prevent the unintentional disclosure of government material.

This incident highlights that anyone can mistakenly upload sensitive data to a public tool. Even the head of CISA.

Key Differences Between Public and Enterprise AI:

• Data Privacy: Enterprise versions (like Microsoft Copilot for 365 or Gemini for Workspace) keep your prompts and data within your organizational "cloud boundary." Your information is not used to train the underlying public models.
• AI Search and Permissions: With Enterprise AI, the tool can surface any document a user has permission to see. This makes cleaning up your SharePoint or Google Drive permissions essential to avoid sensitive files being inadvertently surfaced via AI search. Pay attention to files that have been shared with "anyone with this link" because Copilot and Gemini will view that as granting permission to anyone searching. Finally, spend time on staff training on how to save and share files so that permissions will need less clean up going forward.
• Commercial Protections: Enterprise licenses include copyright indemnity that are absent in public versions.
• Security: Enterprise licenses give IT management and administrative controls which are essential to securing your nonprofit's valuable data.

Resources:

Trump’s acting cyber chief uploaded sensitive files into a public version of ChatGPT from Politico by John Sakellariadis, published Jan 27, 2026. https://www.politico.com/news/2026/01/27/cisa-madhu-gottumukkala-chatgpt-00749361

"The interim head of the country’s cyber defense agency uploaded sensitive contracting documents into a public version of ChatGPT last summer, ... The material included CISA contracting documents marked 'for official use only,' a government designation for information that is considered sensitive and not for public release."

Microsoft Copilot vs. ChatGPT: Data Protection Explained from Community IT.

"If you are using Copilot with a 365 subscription, your prompts and data are not used to train the underlying large language model. It keeps your data within your enterprise cloud boundary... This protection only applies when you are signed in to an eligible work or school account."

Upcoming Webinar: Verifying Your AI Security

Join Community IT CTO Matt Eshleman on February 25th to learn how to distinguish between public and enterprise accounts. Register here: How to Use AI Tools Safely at Nonprofits

_______________________________
Start a conversation :)

• Register to attend a webinar in real time, and find all past transcripts at https://communityit.com/webinars/
• email Carolyn at cwoodard@communityit.com
• on LinkedIn

Thanks for listening.

Panel Discussion with Matt Eshleman, Steve Longenecker, Jennifer Huftalen, and Carolyn Woodard

Our experts answered your questions about where nonprofit tech is going next.

In part 1, Community IT senior staff discuss nonprofits and AI, and updated cybersecurity trends to be aware of. In part 2, they discuss updates to Microsoft and Google Workspace, and take audience Q&A.

AI, Cybersecurity, Google Workspace v Microsoft Office, Gemini v Copilot or ChatGPT or another generative AI tool, AI agents, AI FOMO, data data data, safety and security of your staff, budgeting for and maintaining basic IT, not to mention fancy IT … anything else you want to know about?

We don’t have a crystal ball but we do know our way around nonprofit IT.
We’ll look back at the trends of 2025 and what we got right last January, and we’ll look ahead to make predictions for 2026.

The nonprofit tech roundtable is always one of our most popular webinars every year. As with all our webinars, this presentation is appropriate for an audience of varied IT experience. Community IT is proudly vendor-agnostic, and our webinars cover a range of topics and discussions. Webinars are never a sales pitch, always a way to share our knowledge with our community.

_______________________________
Start a conversation :)

• Register to attend a webinar in real time, and find all past transcripts at https://communityit.com/webinars/
• email Carolyn at cwoodard@communityit.com
• on LinkedIn

Thanks for listening.