Are you struggling to articulate what your nonprofit actually needs from an IT provider? In this episode, host Carolyn Woodard and Community IT CEO Johan Hammerstrom discuss the rise of the generic, AI-generated Request for Proposal (RFP). While it is tempting to use AI to handle the heavy lifting of technical writing, doing so often results in a document that lacks the heart of your organization’s mission.

Johan explains why a successful RFP is less about technical jargon and more about your unique business needs. When you rely on a generic template, you end up with a generic partner. This conversation offers a roadmap for moving beyond checklists to find a support model that actually fits your culture and budget.

Johan and Carolyn explore the essential process of defining your requirements, including:

• The AI Pitfall: Why using AI to write an RFP without deep organizational context leads technical jargon. If you can't understand exactly what your rfp is asking for, neither will the vendors.
• The Thinking Process: A look at why the act of writing—rather than just the final document—is a vital exercise in disciplined thinking and clarity for your leadership team.
• Staff Feedback: How to gather input from your team to identify where legacy systems or siloed tools are creating daily friction and missed opportunities.
• Finding a Partner: Practical advice on how to draw out the unique requirements of your nonprofit to ensure your next IT provider is a true partner, not just a vendor.

A key part of this search is recognizing why many nonprofits feel dissatisfied with their current support. Johan identifies three specific pitfalls that occur when working with a regular, for-profit focused Managed Service Provider (MSP):

1. The Culture Gap: Most MSPs are geared toward a bottom-line, efficiency-first mindset that can feel brusque, abrasive or dissonant when it comes up against a people-centered nonprofit culture.
2. Misaligned Logic: Standard providers often recommend solutions based on revenue generation, failing to understand the resource-constrained and programmatic realities of the nonprofit sector when making IT investments or dealing with legacy IT.
3. The Priority Problem: In a large, general-market firm, smaller nonprofit accounts are often deprioritized in favor of more lucrative corporate clients, leading to inconsistent support, junior-level staffing, and frustration.

If you feel your current provider doesn’t quite get you, or if you are preparing to search for new support, this episode will help you ask the right questions of your AI tools, your staff, and your potential partners.

Resources Mentioned in this Episode:

Link: How to Vet an MSP for Your Nonprofit

Link: How do I Know if an MSP is Right for my Organization?

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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.

In this Nonprofit AI Podcast midweek check-in, Carolyn explores what it means to have agency in the age of AI. With so much pressure to adopt new tools, it can feel like nonprofits have no choice — but Carolyn makes the case that you and your organization have more power than you think, both in the tools you choose and the advocacy you pursue.

The conversation covers the environmental and community impacts of AI infrastructure, and what nonprofits can actually do about it. Carolyn discusses:

• Why individual AI use matter less than local and collective advocacy around data center regulation.
• Advocacy looks different in different locations where data centers are going in at a furious pace. Water issues? Electricity costs? Sites? Your advocacy should be local too.
• The community impacts of data center siting are complex — Carolyn gave just one example of institutional racism and the displacement over time of historic Black landowners in Northern Virginia.
• Creative policy models from Europe that nonprofits can advocate for in their own communities.
• You can align your AI tool choices with your organization's values — and why that matters.
• An update on Anthropic's lawsuit against the Department of Defense over its supply chain risk designation.

As AI infrastructure expands so quickly, Carolyn encourages nonprofits to stay engaged — using AI intentionally while advocating for the communities and values they serve.

Resources Mentioned:

• Webinar: AI Reluctance for Nonprofits, Josh Peskay and Kim Snyder, Meet the Moment: https://www.roundtabletechnology.com/news-and-events/webinar-library/thank-you/ai-resistance-for-nonprofits
• TechSoup AI Training: https://techsoup.course.tc/catalog/exploring-ai-with-microsoft-tools
• Anthropic vs the Pentagon to date: https://techcrunch.com/2026/03/09/anthropic-sues-defense-department-over-supply-chain-risk-designation/
• https://www.npr.org/2026/03/09/nx-s1-5742548/anthropic-pentagon-lawsuit-amodai-hegseth

_______________________________
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.

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.

They were only able to answer a few questions from registration and the audience during this webinar; you can find more questions answered on our reddit community page: https://www.reddit.com/r/NonprofitITManagement/ or in the transcript on our website here: https://communityit.com/webinar-how-to-use-ai-tools-safely-at-nonprofits/

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.

In this Nonprofit AI Podcast, Carolyn explores the complex intersection of nonprofit values and AI vendor ethics. Following a high-profile public dispute between the Pentagon and major AI providers, we look at what these corporate decisions mean for organizations that prioritize mission-aligned technology.

The conversation covers the practical side of AI safety, moving beyond the headlines to answer urgent questions from our recent webinar. Carolyn discusses:

• The ethical ripple effects of the Anthropic and OpenAI rivalry regarding government contracts.
• Why enterprise-level licenses are the primary recommendation for protecting sensitive nonprofit data.
• How to navigate privacy when using AI for board meeting transcriptions and note-taking.
• Practical steps to turn off model training in freemium tools like ChatGPT and Gemini.
• The existential question: Is adopting AI truly inevitable for the nonprofit sector?

As AI continues to disrupt education, health, and environmental sectors, Carolyn discusses the importance of intentionality—whether your organization chooses to opt in or opt out.

Resources Mentioned:

• Community IT Subreddit Webinar Q&A: https://www.reddit.com/r/NonprofitITManagement/comments/1rekaqk/qa_how_to_use_ai_tools_safely_at_nonprofits/
• LinkedIn Guide: Turning off AI model training from Kim Snyder, AI for Nonprofits Trainer at Tech Soup and Meet the Moment
• Upcoming: Part two of our AI safety webinar series with Matt Eshelman. Full video here: 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.

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.

_______________________________
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.

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.

_______________________________
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• Register to attend a webinar in real time, and find all past transcripts at https://communityit.com/webinars/
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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.

_______________________________
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
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Thanks for listening.