Like podcasts? Find our full archive here or anywhere you listen to podcasts: search Community IT Innovators Nonprofit Technology Topics on Apple, Spotify, Google, Stitcher, Pandora, and more. Or ask your smart speaker.
Good — I can see the full page structure clearly. The Ian episode uses a bold H2 subtitle, an intro narrative section, Key Takeaways with bold headers, Resources Mentioned, and Presenters bios. I have everything I need to match that format and voice. Here’s the episode description:
Carolyn Woodard talks with Cheryl Contee, co-founder of Brightworks AI and Change Agent AI and co-author of the Amazon bestseller AI for Nonprofits: Putting Artificial Intelligence to Work for Your Cause, about what it really means for a nonprofit to adopt AI responsibly and with purpose. Cheryl is a pioneering technology entrepreneur recognized by Fast Company, Harvard’s Berkman Center for Internet and Society, and The Root 100, and has appeared in the Washington Post, New York Times, CNN, and the BBC.
The conversation starts with a reframe that many nonprofit leaders need to hear: AI is not something you decide whether to use. It is already built into your email, your CRM, your fundraising platforms, your productivity software. The real question is whether your organization is using it intentionally, ethically, and in service of your mission — or just letting it happen to you.
Cheryl and Carolyn push back on the fear that AI will eliminate nonprofit jobs. In a sector where one person routinely does the work of five, AI is far more likely to function as a force multiplier: a tireless research assistant, a scheduling agent, a first-draft writer that frees your team to focus on the human work that only people can do. Cheryl shares a vivid example from her own experience — a presentation that would have taken hours took 30 minutes, leaving her enough time to go to yoga and take a nap — as a practical illustration of what that kind of time recovery can feel like.
The conversation also gets concrete about where to start, how to build a prompt library, what AI does and doesn’t do well, and why the organizations seeing the most success with AI are the ones treating it as an ongoing learning journey rather than a one-time implementation.
Nonprofit leaders have a role to model. The success of AI for Nonprofits in the “office automation” category — not just the nonprofit or AI categories — suggests that people are looking to mission-driven organizations for cues on how to implement these tools ethically and effectively. There’s a leadership opportunity here for nonprofits willing to take it.
Resources Mentioned
Cheryl Contee is a Co-Founder at BrightWorksAI.com. She’s a pioneering technology entrepreneur and digital transformation expert. Cheryl is renowned as a trailblazing mission-driven startup founder. She inspires audiences globally as a leading voice on innovation & impact. She has co-authored a bestselling new book called “AI for Nonprofits: Putting Artificial Intelligence to Work for Your Cause” sharing insights from 57 AI experts helping nonprofit leaders embrace new tech.
Cheryl Contee was CEO at The Impact Seat Foundation which is working to create a world in which women can succeed as business leaders. She is the author of the Amazon bestseller Mechanical Bull: How You Can Achieve Startup Success. She’s the host of the podcast Make The Most. Cheryl was a co-founder of social marketing software Attentive.ly at Blackbaud, the first tech startup with a black female founder on board in history to be acquired by a NASDAQ-traded company. Her company Fission helped write the early source code for Crowdtangle, earning sweat equity in a successful social enterprise startup acquired by Facebook in Dec 2016. Cheryl is proud to be a co-founder of the tech inclusion initiative #YesWeCode (now DreamCorps Tech).
She was the co-founder of Jack and Jill Politics writing as “Jill Tubman” on the leading top black audience targeted blog during the 2008 and 2012 election cycles. Cheryl has been listed among The Influencers 50 in Campaigns and Elections magazine. Cheryl was named as an Affiliate of Harvard University’s Berkman Center for Internet & Society. She was inducted into the first The Root 100 list of established and emerging African-American leaders. Huffington Post included her as one of the Top 27 Female Founders in Tech to Follow on Twitter in 2011, as did Black Enterprise. Fast Company named her one of their 2010 Most Influential Women in Tech.
Cheryl has been featured in many media outlets including Washington Post, New York Times, Vanity Fair, San Francisco Mag, C-SPAN, Black Enterprise, BBC, MSNBC & CNN. She has served on numerous boards and advisory committees including New Media Ventures, Social Venture Circle, Center for Cultural Power, Hopewell Fund, Netroots Nation & Greenpeace USA.
Books Highlighting Cheryl’s work Include:
Keep Marching: How Every Woman Can Take Action by Kristin Rowe-Finkbeiner
How to Be Black by Baratunde Thurston (NY Times Bestseller)
Campaign Boot Camp 2.0 by Christine Pelosi
Responsible Entrepreneur by Carol Sanford
Happy Healthy Nonprofit by Beth Kanter
Carolyn Woodard is currently head of Marketing and Outreach at Community IT Innovators. She has served many roles at Community IT, from client to project manager to marketing. With over twenty years of experience in the nonprofit world, including as a nonprofit technology project manager and Director of IT at both large and small organizations, Carolyn knows the frustrations and delights of working with technology professionals, accidental techies, executives, and staff to deliver your organization’s mission and keep your IT infrastructure operating. She has a master’s degree in Nonprofit Management from Johns Hopkins University and received her undergraduate degree in English Literature from Williams College.
She was glad to have this conversation with Cheryl Contee on AI for Nonprofits – the book, the experience, the wisdom, and the practical insights.
Community IT has been serving nonprofits exclusively for twenty-five years. We offer Managed IT support services for nonprofits that want to outsource all or part of their IT support and hosted services. For a fixed monthly fee, we provide unlimited remote and on-site help desk support, proactive network management, and ongoing IT planning from a dedicated team of experts in nonprofit-focused IT. Our clients benefit from our IT Business Managers team who will work with you to plan your IT investments and technology roadmap if you don’t have an in-house IT Director.
Being 100% employee-owned is important to us and our clients. It is an important aspect of our culture as a business serving nonprofits exclusively for 25 years.
We constantly research and evaluate new technology to ensure that you get cutting-edge solutions that are tailored to your organization, using standard industry tech tools that don’t lock you into a single vendor or consultant. And we don’t treat any aspect of nonprofit IT as if it is too complicated for you to understand.
We think your IT vendor should be able to explain everything without jargon or lingo.
If you can’t understand your IT management strategy to your own satisfaction, keep asking your questions until you find an outsourced IT provider who will partner with you for well-managed IT.
More on our Managed Services here. More resources on Cybersecurity here.
If you’re ready to gain peace of mind about your IT support, let’s talk.
Carolyn Woodard: Welcome everyone to the Community IT Innovators Technology Topics podcast. I’m Carolyn Woodard, your host, and today I’m so excited to be talking with Cheryl Contee about AI. So, Cheryl, would you like to introduce yourself?
Cheryl Contee: Yes, Carolyn. I am so thrilled to be here with you today. Thank you so much for inviting me. I’m Cheryl Contee, as Carolyn mentioned. I am the co-founder of Brightworks AI, which is a nonprofit AI adoption consultancy for nonprofits.
I am also the co-founder of Change Agent AI, which is an alternative LLM to the big ones like OpenAI, Google, or Anthropic, for those who want something that’s eco-friendly, data private, and data secure for sensitive populations, and trained on nonprofit sector values.
I am also the author of AI for Nonprofits: Putting Artificial Intelligence to Work for Your Cause, available on Amazon. Day one bestseller. It’s still selling out.
Carolyn Woodard: I have it, and I said before we started talking, I’ve only really dipped into it, but I just love the structure. It’s very clearly laid out. You have guest authors on the different pieces of the different chapters about how nonprofits can be using AI. So I am a fan so far. I can recommend it.
Cheryl Contee: Oh, thanks. Well, it’s very practical and tactical. For those folks who are like, okay, I’m ready, let’s roll up our sleeves and figure this out, it’s very much a field guide.
In part, I wrote the book because I was hearing some nonprofits say things like, “Well, here at X Organization, we won’t be using AI.” To which I’d be like, “Oh, sweetie, honey, baby doll, I don’t think you understand what’s happening.”
You’ve been using AI for 10 to 15 years. Moreover, it’s been using you. That’s called classifier AI. That’s your spell checker, that’s your spam filters, that’s how Instagram knows for sure you want those shoes and will get them to you in two days, and you can actually watch the truck drive to your house on the app.
Of course, 2022 was sort of the big bang of generative AI, AI that can create. And I think what’s interesting about that, Carolyn, is that a lot of people don’t realize that moment was literally the fastest technology adoption in history. It took literally 38 years for radio to reach 50 million users. It took seven years for the internet to reach 50 million users around the world.
Carolyn Woodard: Yeah.
Cheryl Contee: It took two months, two months for ChatGPT to reach 500 to a million users. And that has never happened before. That is unprecedented. We’re moving from generative AI, AI that can create, which is very important, into agentic AI, which is AI that can think, plan, and act.
I think it’s really important for people to plan so that they don’t fall behind.
Carolyn Woodard: Yeah, I’ve been hearing from a lot of people at nonprofits and in the philanthropy field that it just feels like this tidal wave that’s washing over us. And one thing I loved about talking with you earlier was that you are able to talk about it in a way to kind of return agency to people who are using it. So I’m really excited to have this conversation.
Cheryl Contee: A hundred percent. I mean, look, AI is becoming infrastructure. Whether you like it or not, it’s built into your email, it’s built into your CRMs, it’s built into your fundraising platforms, your research tools, your productivity software. It’s just going to be normal. It’s like email, it’s Wi-Fi, it’s spreadsheets. It’s just there.
So, really, the question isn’t like, should my nonprofit use AI? Yes, and again, that’s actually not a choice, sweet pea. Let’s all get on the same page there.
It’s really about how do we use AI responsibly and creatively and powerfully in service of the mission that we’ve taken on? There’s just this amazing opportunity for nonprofits, for people who are guided by values and mission, to serve more people, understand their communities better, reduce the administrative burden, unlock new insights, predictive analysis, and just scale your impact.
What if you could get more done, like 10x in a day? How meaningful would that be to the work that you do?
I know a lot of people, Carolyn, are freaked out about, well, if I let AI in, it’s going to take my job. And that might be true in some other sectors, but I have yet to encounter the nonprofit that has too many people and too much money to accomplish their incredibly ambitious mission. So that’s just not a real thing.
Instead, here’s what I want for you all. The first time I used ChatGPT, I’ve since migrated over to Claude and Change Agent, but I had a presentation to put together. I had my coffee, I was settled down, I was ready to park it for the next few hours, which is normally how long it took to do it from scratch, and I was done in basically 30 minutes.
And Miss Carolyn, I was beside myself, I did not know what to do. I went to yoga and then I took a nap.
And I want that for you listening, because this is a really challenging time that we’re living through, and the work that you’re doing is really challenging.
Not only can you maybe get more done in a day, but maybe you can have more time for you in a day so that you are sustainable.
Carolyn Woodard: Yeah, I heard someone describe it as like the most amazing executive assistant you’ve ever had or could have, because they’re so in tune with how you work and what you want to do. And what nonprofit staff person has an assistant? That just doesn’t exist.
Cheryl Contee: Exactly. What if you had five digital employees? I have a scheduler now, Lexi at skej.com, S-K-E-J dot com. I struggle to cope with this time and place, let alone other times and other places. So that is a really big help to me, having an AI agent.
A lot of people, I will say 80% of people, have no idea that Lexi is not a real person. Even though it says at the bottom, “Lexi is an AI robot,” they don’t know, and they don’t care. They’re just trying to find a time. And I, a research assistant, an executive assistant, just what if you had more hands? What if there were three of you or five of you? That’s pretty cool, I think.
I think instead of thinking about just tools, it’s mission first, technology second. I really try to encourage people to think not what shiny fancy AI tool should we be adopting, but what are the problems we’re trying to solve, and what AI tools might fit the shape of that challenge or that problem.
I believe that AI is an amazing intervention for what are the things, the tasks on your team’s plate that they hate the most? What are the things that are the most time-consuming, repetitive, tedious, expensive? Find an AI tool that fits the shape of that hole in your life. Because what if you got someone else to do the things that you hate doing, so you can do more of the things that you love, and the things that only human beings can do.
Carolyn Woodard: Yeah. I feel like we just talked about that. Manpower might be a major challenge of most nonprofits. So using AI to address that problem, instead of saying, “Oh, there’s this tool that does this thing, do I have something that fits the thing that it does?” Yeah.
Cheryl Contee: Exactly. How are you using AI, Carolyn? I’m curious.
Carolyn Woodard: Well, I actually just had this happen the other day. Every month I have to download a bunch of CSV files from Zoom about our webinars, that tell our attendance and the survey responses, and all the stuff I want to know about how we can make our webinars better.
And every month, for years, I have put that all manually into a spreadsheet. And I was doing it as I always do, and I suddenly, in the midst of having done the first sheet, was like, hang on, I’m going to ask Claude. And it literally took, I mean, it may have taken about as long.
It took about 45 minutes, and it was so interesting because it was like co-creating it with me. It would do something and say, does that look right? And I’d say, oh no, the headers are off by one, can you move them over to the left one? And it would go away and come back and say, well, how about this? And I’d say, oh, that’s great.
It was just really energizing. And it took about 45 minutes, which is about how much time it would take me to do it myself. But next month, it made a little agent for me, which in Claude is called Projects. So next month I just drop my CSV files in there and it’s going to do it for me. We’ll see what it does.
But I was just really energized and excited to have accomplished something like this with this co-creator, like executive assistant, intern, but a really good intern.
Cheryl Contee: Yeah, like the smartest intern ever. It can do a lot of things, but it doesn’t have your lived experience, your context, your meaning, your quality control.
And even though in this case it was 45 minutes of co-creating and teaching it how to do it, it was probably way less tedious than having to copy field by field or import it.
And the next time you do it, it’s probably going to remember and be like, oh yeah, this thing that we did before, I know how you like it. I know you like it sunny side up with a little salt and pepper. Yes, ma’am.
Well, there are a lot of common pitfalls. It can go sideways, AI. But you obviously are a baller, Carolyn, you don’t need any help.
Carolyn Woodard: But for those of you out there, a lot of marketers have been using AI for a little while. There’s a lot of good answers because it has a lot to work with, even if you’re using the freemium tools. I think the takeaway is: keep using it, keep trying it, because you get better at using it too.
Cheryl Contee: Yes, exactly. I think the first place to start is: pick one thing that you hate doing. What is the thing that you always shove to 4 p.m. on Friday because it is your least favorite thing?
Pick one workflow, test one to two AI tools on that workflow. One of my favorite sites, I think you know about this one, Carolyn, it’s called “There’s an AI for That” dot com. Literally, that’s the name. Because you don’t have to use Claude or Gemini or ChatGPT. You can, and those can do a lot of things, particularly Claude these days can do a lot of things. But there are literally thousands of AI applications, and it’s fun to just go there and see the breadth of, and just the energy in, the AI creation community.
I trust and believe you will find at least one to two AI tools that can help you with that specific task or workflow. Then compare the time saved or the quality improved, just like you did, Carolyn. In this case, it didn’t necessarily save you time on the first go-round, but it was a far more pleasant experience.
Quality of life is sometimes just as important as time saved or money saved.
And then tell people about it. There’s a lot of AI happening in the shadows. Everybody wants to be better at their job, but nobody wants to get fired. So they’re like, I’m just going to use AI over in this corner.
I think it’s important to tell people about your workflow, your experiment, your learning cycle, and then you can iterate and expand and maybe pick up some ideas from other folks. That’s just a very simple AI “let’s get started” playbook.
Carolyn Woodard: Yeah, I love it. At our organization, we use Teams, and so we have a dedicated AI channel where we all share things like, I did this, I was trying to do this, it didn’t totally work, what do you advise? We have a very active conversation going on over there.
Cheryl Contee: Right, which is exciting. And if you’ve got something that’s structured or pattern-based, or really text-heavy, or there’s math, or things need to go in different cells in your spreadsheet, AI is really great for that kind of thing.
It is less great for high-stakes decisions, for sensitive human interactions. Do you have a context-loaded judgment call to make? Which in these times is very real.
If it’s a thing that’s going to require lived experience, or trust, nuance, accountability, I think humans need to stay in the lead. And I think humans need to stay in the loop.
As you know, Carolyn, “human in the loop” is literally an AI technical term, which means you can’t just let the agent do whatever. You need to stay in the driver’s seat because there’s a lot it doesn’t know, it doesn’t understand.
It’s like a really smart intern that doesn’t even know what it doesn’t know. So someone always needs to be reviewing, checking, driving the process, ensuring quality control.
Cheryl Contee: In terms of leadership habits that I recommend, and I know there are a lot of leaders listening, we just talked about normalizing learning around AI. I think what I’ve seen, just as you were talking about, Carolyn, is creating regular opportunities for your staff to share experiences, prompts, lessons learned, just to encourage that curiosity and safe exploration.
I just did a talk in Palm Springs with the head of Board.dev and the head of social impact at GitHub. Sid Espinoza was saying that at Microsoft, which owns GitHub, it’s now in their performance reviews: how much they’ve used AI and how they’ve been using AI. Literally every staff person has to account for that.
In part, it’s to really encourage people to explore, to be curious, to jump in feet first to a certain extent. I think it’s super important also to capture and share what works, as you’ve been doing. Document your successful use cases. What are your workflows?
Create a prompt library. A lot of people will just sit in front of the blank prompt screen, and that’s okay.
Carolyn Woodard: They say, what am I supposed to ask?
Cheryl Contee: That’s okay. Prompting is a whole skill. We have a couple of chapters about that in the book. Being good at talking to the robots is literally a job.
So create a prompt library where people can be like, all right, I want to do some prompting, I want to start building some stuff around my fundraising. What are some fundraising prompts I can get started with that are relevant to the work that we do? Or email templating, etc.
Carolyn Woodard: I’ve seen that done as prompting recipes, where it’s like: you want to give it the context, and then you want to talk about what you want it to do, like a guide for how to create a good prompt.
Cheryl Contee: A hundred percent. And then staying connected to how this is all evolving. There are going to be bumps in the road.
I’m not trying to be Pollyanna about this. We’re going through kind of like, you know that book The Jungle by Upton Sinclair? This is the jungle right now, okay.
But what was interesting about AI for Nonprofits when it came out last summer, it was a day one bestseller, as I mentioned. It reached the top five in the AI category on Amazon. It reached the top ten in business and finance, which is a huge category. And it was number one in office automation, which is a strangely big category on Amazon, for weeks.
It was on there for weeks, and my co-author Darien Rodriguez Heyman and I went back to our publisher and we’re like, did you code it right? Because we are trying to reach nonprofits.
And they said, yeah, no, it’s right, it’s Amazon, Amazon is putting it in front of people.
My takeaway from that, Carolyn, is that people are looking to nonprofit leaders for cues, for ideas, on how to implement these tools, not just powerfully, not just efficiently, but ethically.
So this is an opportunity not to sit in the backseat and see what happens, but to actually take a leadership role in modeling how you do this right. That’s the opportunity.
I hope that you will tap into great resources like NTEN.org, which has some great resources. TechSoup these days, I was just talking to Marnie Webb at NTEN, who has a great set of resources too. There’s a lot out there to keep learning as tools and best practices evolve.
Carolyn Woodard: Yeah, and that’s something that nonprofits really have in our DNA, is that we always talk to our peers, we always talk, we have all-staff meetings. So sharing in those spaces and finding the resources, I think that is a big part of it that may be less challenging than some of the other pieces.
Cheryl Contee: Absolutely. There are some pitfalls. Maybe we can talk about that really quickly.
Obviously, you don’t want to chase every cool new tool that comes out. We talked about that already.
You don’t want to skip training your team. Upskilling is really important. Even the most awesome, cool tools aren’t going to have a lot of impact if people don’t feel confident using them. If you spend $30 a seat for 10 people and zero people use it, that’s a hundred percent loss. Don’t do that.
Obviously, ignoring ethical considerations: you want to make sure you’re thinking about bias, about confidentiality and sensitive data.
But really, the one that I see a lot is just expecting immediate magical transformation. And that’s not really going to happen.
AI is really more of a journey. You’re starting a learning process. Hopefully you’re getting your team on the path to experiment, to discover what works, discover what doesn’t. It’s okay if it doesn’t fit, that’s totally fine. How do you refine and optimize your workflows?
The idea is to gradually build your capacity over time. So instead of thinking about AI as a single breakthrough moment, think of it as that journey, that road you’re getting onto.
Carolyn Woodard: I think in my own experience too, and I’ve heard this from other people, the more you use it, the more it strikes you how you can use it. Like my little example of doing this thing I have to do every month, and suddenly thinking, “oh, I could ask AI!”
And the more you have those moments around your own productivity, the more working at a nonprofit, you could have those lightning moments where you’re like, what if we combined the census data with our population data? You start thinking about your mission and ways that AI could transform it as well.
But you can’t start out with, let’s change our mission all around. The more you learn about how AI works, the more you can see where those inflection points might be.
Cheryl Contee: Exactly. The organizations that I’m seeing that are being successful with AI aren’t the ones that are trying to get everything right right away. They’re the ones that want to just learn and keep learning as things move along.
Well, this has been awesome, Carolyn.
Carolyn Woodard: I’m so grateful. Thank you so much for your time and your words of wisdom in this book, which I will put everything in the show notes. We’ll have a bunch of URLs and links there to the stuff that we talked about today. But again, Cheryl, just thank you so much. I really appreciate this conversation.
Cheryl Contee: Oh, thank you, Carolyn, and thank you all for listening. Appreciate it.
As advocates for using technology to work smarter, we’re practicing what we recommend. This transcript was drafted with the assistance of AI, and is not a verbatim transcript. The content was edited for clarity, and was reviewed, edited, and finalized by a human editor to ensure accuracy and relevance.
Wednesday May 27th at 3pm Eastern join Nura Aboki to learn how to prioritize intentional AI implementation and build AI policies.
Fill out the form below to request a quote. We’ll be in touch shortly to discuss your needs and take the first step toward better nonprofit IT.