If you have wondered about the real difference between using a free tool like ChatGPT and an enterprise-level solution like Microsoft Copilot or Google Gemini, this episode will provide much-needed clarity. While the potential for efficiency is high, many nonprofit leaders are rightfully concerned about data security and how to ensure they are using these models safely.

In part one from their recent webinar, Community IT Outreach Director Carolyn Woodard is joined by Chief Technology Officer Matt Eshleman to demystify the current AI tool landscape, particularly for data security.

In part two, Matt and Carolyn go over ways to tell you are logged in to your official account or not, the importance of continuous and iterative staff education, and how (and why) to get started creating AI policies to share with staff.

This episode one covers:

• The distinction between freemium AI models and enterprise-protected tools.
• The AI continuum, ranging from assistive technology to workflow assistants to autonomous agents.
• A breakdown of pricing tiers and what nonprofits can expect in terms of data privacy and functionality.
• Practical advice on why terms and conditions matter when protecting your organizational data.

Whether you are already using AI daily or are just beginning to explore its possibilities, this discussion offers a professional and grounded look at how to navigate these tools securely.

_______________________________
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• 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.

Resources shared in this episode:

Gallop Poll January 2026 on AI use: https://apnews.com/article/ai-workplace-gemini-chatgpt-poll-4934bc61d039508db32bc49f85d63d99

Build Consulting 5 Category AI Implementation Framework by Kyle Haines: https://buildconsulting.com/blog/a-strategic-framework-for-nonprofit-ai-investment/

1: Return on Investment - what are you trying to do, and is an AI tool the best way to do it?

2. Technical and Data Feasibility - are you ready? Is your data ready?

3. Mitigating AI Risks - legal, ethical, reputational...

4. Anticipating Costs - AI tools are not free

5. Change Impacts - making sure intentional change management is in place.

How AI is changing search, Yoast wrap up from 2025: https://yoast.com/seo-in-2025-wrap-up/

AI Literacy Measures and Suggestions from US Department of Labor: https://www.dol.gov/sites/dolgov/files/ETA/advisories/TEN/2025/TEN%2007-25/TEN%2007-25%20%28complete%20document%29.pdf

AI Literacy Measures:

1. Understand AI Concepts

2. Explore AI Uses

3. Direct AI Effectively

4. Evaluate AI Outputs

5. Use AI Responsibly

Delivery Principles for AI Literacy Growth

1. Enable Experiential Learning

2. Embed Learning in Context

3. Build Complementary Human Skills

4. Address Prerequisites to AI Literacy

5. Create Pathways for AI Learning

6. Prepare Enabling Roles

7. Design for Agility

Webinar: How to Use AI Tools Safely at Your Nonprofit with Matthew Eshleman. https://communityit.com/webinar-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.

In this episode host Carolyn Woodard is joined by Norwin Herrera, IT Business Manager and Team Lead at Community IT. Together, they walk through a real-world case study of a public charter school that implemented a Single Sign-On (SSO) platform called Clever that can solve cybersecurity and accessibility challenges for adult or child students.

Strategic IT Leadership for Nonprofits

Unlike a traditional account manager, an IT Business Manager (ITBM) acts as a strategic partner, helping nonprofit leadership understand the technology landscape and make informed decisions that align with their mission. The ITBM role is unique to Community IT and is an example of a commitment to partnering with clients over the long term.

In this case, the goal was to find a SSO solution that could handle a complex mix of Chromebooks and Windows devices while remaining user-friendly for both adult students and faculty.

The Power of Single Sign-On

SSO acts as one door for all of your doors. By using Clever as an identity manager, the organization was able to:

• Enhance Cybersecurity: Centralizing access allows for immediate offboarding. If a student or staff member leaves, closing one account automatically secures access to all others, prevents fraud, and saves money.
• Automate User Provisioning: Through zero intervention integration with the Student Information System (SIS), accounts are created or deactivated automatically based on enrollment status.
• Improve User Experience: Students no longer need to remember multiple different passwords for Google, Microsoft, Zoom, and Slack for example. One password provides access to all the apps they have access to as a student using a school device.
• Reduce Administrative Costs: Norwin breaks down the ROI of SSO, comparing a small per-user fee against the hundreds of hours of manual labor required to manage accounts individually.

Change Management and Successful Implementation

A successful IT project is about more than just software; it is about people. Norwin explains why this project resulted in zero tickets and no complaints: it started with leadership buy-in and a commitment to clear communication.

Whether you are an executive at a school or a volunteer board member at a community nonprofit, this episode offers practical insights into how integrated cybersecurity and strategic IT planning can save your organization time and money.

Listen in to learn how your organization can move toward a more secure and efficient digital future by subscribing to the Community IT Innovators Technology Topics podcast.

_______________________________
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.

Nonprofit AI: Vetting Your Tools and Understanding AI Agents

In this midweek AI check-in, Carolyn Woodard explores how nonprofit leaders can make informed, safe decisions in an increasingly crowded technology landscape. The episode begins with a review of a new AI Tools Safety Guide specifically designed for the nonprofit sector. This resource evaluates popular tools based on the criteria that matter most to mission-driven organizations: data privacy, security, and ethical responsibility.

Carolyn also demystifies the concept of AI Agents. By breaking down the hierarchy of AI—from simple bots and assistants to more autonomous agents—she explains how these specialized tools can eventually handle the busy work of repetitive tasks, such as cross-referencing spreadsheets or organizing files.

Whether you are just starting to draft your organization's AI usage policy or you are looking for ways to streamline your internal workflows, this episode provides practical guardrails for navigating AI adoption at nonprofits.

Featured Resources

• Tool: AI Tools Safety Guide for Nonprofits Visit Meet the Moment A searchable directory of AI tools evaluated for trust and safety by reputable nonprofit technology experts. It’s an ideal starting point for organizations with strict data handling needs and limited research time.
• Template: AI Acceptable Use Policy Download from Community IT IT is better to establish clear principles now than to wait for time to make a perfect policy. This template helps you communicate expectations to your staff and board regarding the use of generative AI.
• Community Discussion: Nonprofit IT Management Join the Reddit Community Have a specific question about an AI tool or a repetitive task you'd like to automate? Connect with Carolyn and other nonprofit professionals on our dedicated subreddit to share insights and ask questions.

_______________________________
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• 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.

Building Stronger Teams: Purposeful Connection in a Remote World

How do you maintain a cohesive, supportive team when the office is now spread across dozens of different locations? In this episode, Carolyn Woodard sits down with Saba Gebru, Vice President of Support Services at Community IT, to discuss the intentional work required to foster teamwork in a remote and hybrid environment.

Saba shares how Community IT transitioned through the pandemic and emerged with a deeper understanding of why social connection isn't just extra—it’s essential for better service delivery.

When technicians feel supported and connected to one another, our clients benefit from the collective knowledge of the entire firm, not just a single individual. We also discuss how to keep team building from feeling mandatory by aligning activities with mission-driven values, such as local volunteerism and servant leadership.

Featured Resources

• Community IT Values: Our Story | Read More Learn more about the core values that guide our team—including balance and transparency—and how these principles help us better serve the nonprofit community.
• Guide: Managing Remote Teams for Nonprofits | View Article For managers looking to refine their remote operations, this guide offers practical tips on the tools and cultural shifts necessary to keep a distributed workforce engaged and secure.
• Case Study: 100% Remote Work Implementation with Microsoft Cloud | Read the Case Study Transitioning to a fully remote model requires more than just a change in mindset; it requires a robust technical foundation. This case study follows a large nonprofit as they navigated a rapid shift to 100% remote work. By leveraging Microsoft Cloud tools the organization was able to deploy hardware and support staff across the country without ever needing to meet in person, proving that with the right roadmap, technology can bridge the gap between physical distance and mission-critical collaboration.

Next Step for Your Organization

Building a strong team culture is an ongoing process, especially in the remote era. If you haven't recently checked in with your staff about what they need to feel connected, consider making it a priority in your next departmental meeting. Start the conversation by asking for feedback on what types of optional social or volunteer activities might resonate with their values.

_______________________________
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.

Nonprofit AI Check-in: Reclaiming Human Rights and Protecting Local Communities

In this midweek check-in, Carolyn Woodard steps back from the technical "how-to" of AI to look at the "why" behind the ethical concerns many nonprofit leaders are feeling. This episode focuses on two significant areas where AI intersects with our core mission of serving others: the protection of basic human rights and the physical impact of the infrastructure that makes AI possible.

First, we explore insights from human rights lawyer Malika Saada Saar on how we can reclaim AI to serve dignity and democracy rather than ceding it to companies that make a profit by exploiting sensitive and marginalized groups.

Second, we look at the reality of the data centers powering these tools—specifically the environmental and economic pressures they place on local residents. Carolyn shares resources on creating Community Benefit Agreements (CBAs) with data centers as a path forward for local communities.

Whether it's protecting a survivor’s right to privacy or ensuring a local community has a say in how a data center is built, these are the human issues that will define how we use technology in the years to come.

Featured Resources

• Webinar: Slow Violence, Fast Tech | Watch on YouTube In this 30-minute session from All Tech Is Human, human rights lawyer Malika Saada Saar discusses the "slow violence" of AI and how nonprofits can advocate for technology designed with consent and safety in mind, particularly for women, children, and marginalized communities.
• Report: Why Community Benefit Agreements are Necessary for Data Centers | Read at Brookings As data centers expand rapidly across the U.S., this Brookings Institution paper explains how "Community Benefit Agreements" (CBAs) can help local leaders and residents negotiate for transparency, environmental protections, and shared economic benefits.
• Community IT Resource: AI Ethics and Policy Webinar | View the Framework If you are ready to start moving from learning to doing, this webinar provides a practical framework for nonprofits to begin drafting their own AI use policies and start conversations around ethics.

Next Step for Your Organization

Does your nonprofit have an AI ethics policy yet? If not, now is the perfect time to start the conversation with your leadership and board. You don't need to be a technical expert to advocate for your organization's values. We encourage you to use these resources to continue your education and ensure that your use of AI remains mission-aligned.

_______________________________
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.

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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• 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.