Community IT Innovators Nonprofit Technology Topics

2025 Nonprofit Tech Round Table pt 1

• Community IT Innovators • Season 6 • Episode 4

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Expert Tips on Current Trends: 
Webinar 2025 Nonprofit Tech Round Table

Join CTO Matthew Eshleman and Director of IT Consulting Steve Longenecker, moderated by Carolyn Woodard from Community IT, in a lively and specific discussion of all things nonprofit tech for 2025 and beyond.

It’s like listening in on your smart friends talking about stuff you need to know about but don’t know who to ask.

Kick off the new year with a new understanding of trends and practices that can help your nonprofit succeed. This is one of our most popular webinars and podcasts year after year for a reason. We don’t believe a lot of lingo or jargon is necessary to understand what you need to know to manage IT.

As with all our webinars, this presentation is appropriate for an audience of varied IT experience. Part 1 covers our introductions, a discussion of hybrid work in the nonprofit context, and tips on new cybersecurity from our expert. Part 2 covers AI, a "grab bag" of new tech and new issues, and audience Q&A.

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. 

Many questions asked at registration or live at the virtual event will be answered in the transcript. 

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Carolyn Woodard: Welcome, everyone, to the Community IT Innovators webinar for the 2025 Nonprofit Tech Roundtable. This is always one of our most popular webinars every year. We have a panel of our senior staff here today to talk about essential trends in nonprofit tech and what that means for nonprofits.

We're going to talk today about hybrid work and whether it really is here to stay or if we'll all be back in the offices in a few years. We're going to learn about new cybersecurity threats and prevention, about the impact that AI tools are having on our work in our sector, and we're going to learn some new updates to Google Workspace, Office 365, some other tools, and some other updates. 

My name is Carolyn Woodard. I'm the Outreach Director for Community IT and the moderator today. Very happy to hear from our experts. Matt, would you like to introduce yourself? 

Matt Eshleman: Sure. It's great to be here and talk about some tech trends for the upcoming year.

My name is Matthew Eshleman and I'm the Chief Technology Officer here at Community IT. I'm happy to say this year, I'll be celebrating my 23rd year at Community IT. Super excited to be here and it's interesting doing these to see just how much technology has changed, particularly nonprofit space over that time. Looking forward to the conversation today.

Carolyn Woodard: Me too. Thank you for joining us. Steve, would you like to introduce yourself? I think you're also going to give Matt a run for his money of how long you've been with Community IT.

Steve Longenecker: I'm like the little brother, no matter how long I stayed at Community IT, Matt has been here longer than me. I've been at Community IT for 20 plus years now, and I am the Director of IT Consulting, and I'm also excited about being on this webinar panel. 

Matt and I have done this webinar together for many years now. Looking forward to it.

Carolyn Woodard: It's always fun. It's a good one. 

Before we begin though, if you're not familiar with Community IT, I'm going to tell you a little bit about us. We're a 100 percent employee-owned managed services provider. We provide outsourced IT support. We work exclusively with nonprofit organizations, and our mission is to help nonprofits accomplish their missions through the effective use of technology.

We are big fans of what well-managed IT can do for your nonprofit. We serve nonprofits across the United States. We've been doing this for over 20 years. We are technology experts, and we are consistently given the MSP 501 recognition for being a top MSP, which is an honor we received again in 2024.

I want to remind everyone that for these presentations, Community IT is vendor agnostic. We only make recommendations to our clients and only based on their specific business needs. We never try to get a client into a product because we get an incentive or a benefit from that.

But we do consider ourselves a Best of Breed IT provider. So, it is our job to know the landscape, the tools that are available, reputable and widely used. And we make recommendations on that basis for our clients based on their business needs, priorities and budget. 

Today, we're going to be discussing several themes with our experts. We know that nonprofits are always facing challenges and sometimes feel more challenging and more stressful than other times. We do know for a lot of nonprofits this is one of those times. It's very challenging and very stressful. We know that nonprofits are used to strategizing lots of different outcomes and being smart about planning. So, we hope today you can take a breath, take a mental break and focus on some specifics around planning for nonprofit IT.

By the end of this session, we hope that you will have learned about this hybrid and remote work discussion and what that implies for nonprofit IT support. Is hybrid and remote work here to stay? We're going to learn about new cybersecurity attacks and prevention. We're going to learn about what you need to know about AI. At the end, which we're going to try and make a lot of time for, we have a grab bag, so other new things in 2025, including some updates to tools that you use. I just want to make sure to acknowledge that, as I said, we have some challenging times for the nonprofit community, that are going to impact how you plan for and invest in your IT. 

Of course, we hope that you keep investing in IT to stay productive and stay active and able to achieve your missions. But there will be economic uncertainty around a lot of issues, trade, inflation, immigration, changes to government priorities, shifting DEI policies, and funding changes related to these changing tides and ideas around the nonprofit role. 

We're invested in nonprofits, and we hope to support you, but just wanted to acknowledge that as we go forward.

Now, I'm going to turn it over to Steve, who is going to take the lead on last year's predictions versus the reality, and then we will jump right into the webinar.


Last Year’s Predictions of Nonprofit IT Trends

 

Steve Longenecker: Sure. So, this webinar, we've been doing this for many, many years, and we do like to look back at what we said last year, and we were joking together, the three of us, at our planning meeting a few weeks ago, that we could almost take last year's slide deck and just copy it and change a few things, and then we could have the same thing again for 2025. There's a lot of truth to that joke, for sure.  

We talked about AI last year, and we got that one right, turns out AI was important last year, it will be important again in 2025. We'll spend some time today talking about AI, so I won't hash it out here. 

We did predict that there would be new cybersecurity threats in 2024, back in last January, and we were right about that. I expect we'll be right if we predict in 2025 there will be new cybersecurity threats. We'll be right about that too, that is an ever-changing landscape. So again, we don't need to get a lot of credit for that. 

We talked about Google Workspace, Microsoft 365, and how that would continue to be of great interest to nonprofits. You live in one platform or the other, and it's probably the most important platform to your overall productivity. A finance department member might care more about their finance system than they do about Microsoft 365 or Google Workspace, but in general, it's the platform we all live in, one or the other. I'd say we back off on that. We'll talk a little bit about this again today, but I would say that in some ways, things have stabilized.  

Microsoft continues to really invest in their platform. I'd say in the long, long view, we have seen Google have periods of intense investment in Google Workspace or whatever the predecessors were named. The platforms had different branding over the years. And then other periods where it's laid a little bit low. And I'd say right now Google's priority is definitely on AI, of which there's an angle for Google Workspace. But I think Google Workspace is getting less attention than it has in some previous years. So that is what it is. We may talk about that a little bit.

And then we're going to start out right here at the beginning by talking about hybrid work. So, yeah, it turns out that you can rinse and repeat on tech predictions these days because the same themes keep coming up year after year. And that's not really a big surprise.


Is Your Nonprofit Going to Keep Working Remotely? Audience Poll

 

Carolyn Woodard: Yes. So, hybrid work, we're going to talk a little bit about that. We wanted you to weigh in. I'm going to go ahead and launch this poll. 

The question is, is your nonprofit going to keep working remotely?

·       And the options you can choose are yes. We are all remote, no office forever. 

·       Yes, we have a hybrid setup. If you have details you want to share with us, you could go ahead and put that in the chat. We know there are lots of different hybrid ways to set up your office. But we have a hybrid setup and we're going to keep it that way. 

·       Another option is yes for now. We are assessing the pros and cons, and we may go back to an office. 

·       The fourth option is no. We tried hybrid and remote work, and we went back to the office. We did an experiment and went back. 

·       Then the fifth option is no, we never went hybrid or remote for most staff. 

·       I apologize. Usually, I put in the none of these apply to me, but I didn't do that. If it doesn't apply to you, just don't answer this question. 

Matt, can you see that?

Matt Eshleman: Yeah, I was waiting! I couldn't see the results coming in, so I was curious to see what it ends up as. 

In terms of the responses for the folks attending today, about 11 percent of the respondents are saying yes, all remote forever. The vast majority of the folks are saying yes, they're hybrid and we like it. That's the vast majority of the respondents, 67 percent. Fifteen percent of folks saying yes for now, assessing pros and cons.

Interestingly enough, nobody said no, they tried hybrid and remote and then went back to the office. Then maybe just a few of the folks that said no, we never went hybrid and remote. I know we have a couple of direct services, health clinics, and food banks.

Steve Longenecker: Someone mentioned being an outdoor educational facility in the chat. Hard to be remote if that's what your organization does.

Matt Eshleman: interesting responses, particularly as we're headquartered in Washington, DC, in particular with the return to office mandate from the federal government. I’ll be curious to see how that potentially trickles down or maybe gives cover for some nonprofit organizations to call staff back to the office as well. They were waiting for a reason.

Carolyn Woodard: Thank you to the people who put in the chat your experience with hybrid work.  

One person said they’re back three days a week. Someone said, hybrid works for everyone, especially during storms or there’s no electricity or water. Someone, as Steve mentioned, said they are an outdoor educational facility, so it is hard to go remote in that situation. And someone said that in-office days are focused on in-person full team or whole department meetings. We do have a client that they went back to the office two days a week, but it’s the same two days for all of the staff, so everyone is in at the same time, and you can get that benefit of popping into someone’s office or meeting for lunch or doing those things. Someone else said, we have been meeting in person once a month and decided we like to see each other, so we’re going to twice a month this year. And someone says, we have an all-hands home week three times a year. So, kind of the reverse of making sure that there's some times when no one is in the office, having some times when everyone's working remotely.  

Thank you so much for sharing that. 

 

Hybrid work is here to stay, or is it?

 

This is what we said last year, and we think this assessment stands for nonprofits generally. But as we've said, the corporate world and federal offices are shutting down hybrid remote work and forcing people back into the offices. 

So, our question is, is the nonprofit world going to stick with hybrid work or eventually follow the corporate and federal world? 

I think Steve, you were going to take the lead on this discussion, but hoping that Matt will chime in as well about the return to physical offices, in terms of nonprofit IT. 

Steve Longenecker: Yeah, it's interesting how our audience polled. I was just sort of doing the mental math. It seemed like 90 percent of the organizations are currently doing hybrid, and only a few of those 90 percent are even really re-evaluating it at this time.

Now, hybrid, of course, doesn't mean fully remote. There is still an office space, there is still, for many, an opportunity to engage face-to-face in team meetings and so on, and I think that works. 

I do think that nonprofits, their selling point in terms of recruiting staff is mission fit. This is your opportunity to make the world a better place, and then also that it might be a nicer place to work than a dog-eat-dog enterprise for-profit world, and that people that are self-selecting to work in nonprofits might be nicer people or whatever. 

Our clients certainly seem, and they're all nonprofits, certainly seem like nice people, generally speaking, so I think that that fits. I think in keeping with that idea that, hey, we may not pay you as well as if you were working in a for-profit law firm. Do you want to work for this nonprofit law firm instead, just to throw out one comparison point. But we do give you work-life balance. You're not going to have to work 65-hour weeks. You might be able to work remotely more often than you would in a commercial setting kind of a thing.  

I think that it makes sense to me that nonprofits would continue to build on the technology that allows people to continue to do their jobs well, even when they're not in an office. 

But I do also wonder, to a devil's advocate part of me, that with a lot of trends, technologically and otherwise, nonprofit organizations oftentimes are, I would say, lagging behind the for-profit space for whatever reason, just more conservative.

So, some of the trends that we saw really going strong in the for-profit space and hit the nonprofit space later include things like IT security and stuff. So, a part of me wonders, hey, is it going to be the case? Because we're definitely seeing, these are big corporations, so there's a scale difference too. Amazon is making everybody come back to the office. Carolyn mentioned all federal employees have to come back to the office, and that's huge for people that have established patterns that work for them that involve working from home at least some of the time.

Is this going to be a place that now forever more is a distinction between nonprofit and for-profit? I don't know. We don't know the answer, but we certainly see our clients embracing hybrid workspaces and taking advantage of it and viewing it as a real advantage.

And Community IT is somewhere between remote only and a hybrid. Matt's in our office today, but it's not that common anymore for us. We'll have meetings in the office from time to time, but many of our staff live all over the country and we rely on virtual meetings to stay in touch. 


Productivity Management of Remote Workers

 

Matt, do you want to talk a little bit about the requests that we've been getting on the, not the security side per se, but what do you want to call it?

Matt Eshleman: Yeah, on the productivity management side. I think that was a new spark or new trend that I saw come to me in 2024. 

As Steve said, we may be nonprofits lagging the for-profit sector. I think from that perspective, we're talking about more maybe draconian or strict management standards.

For a long, long time, we've always said we don't do staff productivity monitoring. There are tools we have as a managed service provider. They're geared towards security, and we are blocking malicious websites. But we're not in the business of reporting on who's going where, what percentage of the day maybe somebody's on the Internet. 

The messaging is really management through your staff relationships. 

But in 2024, I will say I had more conversations with organizations looking at and evaluating or deploying those productivity monitoring tools. Because I think that lack of in-person interaction, being able to drop by and see what somebody's doing, rightly or wrongly, I think organizations are maybe feeling a little bit disconnected from the actual productivity monitoring of staff. Are they really using their time to the fullest?  

Organizations have started to look at those, quote unquote, productivity monitoring tools that would provide some reporting. How much time is Word open on the computer? How many words have been typed? What percentage of time was being used on business websites versus personal or recreational sites? 

I think that is something I'm interested to continue to monitor and follow because it's something that is new. 

I think it does represent a little bit of a shift from a management perspective in terms of how that management staff relationship is working. There's lots of flexibility working from home. But then there is also a sense of, if I can't see somebody doing their work, how do I really measure and gauge their productivity if I don't maybe have other tools or other ways to do that in a good and effective way? 

Steve Longenecker: It's kind of an awful topic. You know, “oh, you're going to count someone's keystrokes or you're going to monitor which websites they visit.” But I also appreciate that when everyone was in the same office, you could sort of walk behind someone and see what was on their screen. And sure, probably people quickly replaced solitaire with a word document when they saw you coming. It’s just a different environment than it is when everyone's working from home. And I'm sure that it's abused. I'm sure it is. I mean, hopefully not much. 

And hopefully the people in this audience have missions that inspire staff to work hard and hire people that are just self-motivated and all of those things. But human beings come in all varieties. And what do you do? How do you know? It's tough.

Carolyn Woodard: I thought an interesting part of this discussion is that there's a lot of management issues with managing remote workers. And so, it would be interesting to see if the nonprofit sector has better practices at managing or having those trust relationships between colleagues and also vertically between direct reports. If the overwhelming atmosphere at nonprofit offices before lent itself better to remote working or hybrid working because there were better relationships between the people.

And you said there's usually a tradeoff with salary (and work-life balance). So, I think it's going to be harder for nonprofits to crack down and say, “you have to be back in the office.”

And then a lot of nonprofits, a lot of our clients gave up their offices during the pandemic. They just went fully remote. So, it wouldn't be the case like Amazon where they had invested in a multimillion-dollar facility, and then everybody was remote because of the pandemic. And now they have to justify having built their office buildings. A lot of nonprofits just don't have that and actually like to have the least overhead of not renting a space for an office.


How to Invest in Remote Work IT

 

Are there particular investments that you need to make to make IT remote work work better that people should be thinking about for the next couple of years? Or is it really just keep doing the remote and hybrid that you've been doing and see what happens?

Matt Eshleman: I think a lot of nonprofit organizations have already made that shift. And I think the technology is now really in a place to support that. I think, at the beginning of the pandemic, that was a big scramble, right? Moving the cloud-enabled platforms away from on-prem physical infrastructure. But I think at this point, among the clients that we manage, the number of servers that we manage has really dropped precipitously. Most of the business applications are all in the cloud.

As long as you have a computer with a good internet connection you can be productive wherever you are. I think that infrastructure has already been deployed at many organizations. I mean, we still see organizations that haven't made that shift, but I think that's a small minority of organizations that we encounter at this point. 

Carolyn Woodard: That makes sense.

Steve Longenecker: I agree with Matt that the technology is there, and I think our clients and probably the people in this audience have already found their way to whatever platforms they use for virtual meetings and so forth. 

We're probably still evolving the way we use those tools. And what I mean by that is, I don't think it's a one-to-one replacement for what we used to do.  

So as just one example, our team, the two teams I manage, I attend huddles with them, and it's easy to do virtually. It's a chance for people to say what they're working on and if they're having any roadblocks. And I know we've mentioned this in other webinars, and it's not like rocket science or whatever, but we never had huddles like that when we were in the office, because it just would have felt redundant, I think, when we could just ad hoc, see each other whenever we want to. But to have a deliberate time for a huddle makes sense in a virtual world. 

One of our audience members talked about good and poor management in terms of getting people to work hard. And I think that takes relationships.

How do you build relationships virtually? You may need to have a different style of meeting with your direct reports than you might have before. Maybe the frequency changes or maybe what you're trying to accomplish in the meeting is different.

I spend a lot more time with my meetings talking about people's families and how they're doing. Just generally more than I probably did in the past where that conversation happened at the water cooler and the meeting was for establishing priorities, finding out what roadblocks were. Now I'm like, well, you know what? This is my chance to make sure that I'm connected to this person who lives three states away and who I only see once a year at our DC week when we all gather in DC.

Anyway, I think that those are the non-technical practices that I think are evolving and we're still finding our way on that, if that makes sense.

Carolyn Woodard: I will just jump in to say, we talked a little bit earlier about sometimes nonprofits are lagging other business practices, but this may be an area where nonprofit management is leading, being able to establish those relationships and being intentional about keeping those relationships going even when you're remote.


New Cybersecurity Threats

 

I think we're going to change gears a little bit here and talk about cybersecurity threats. Matt, you want to take the lead and hit some highlights on cybersecurity?

Matt Eshleman: Yeah. Building off what Steve said, looking back at what we talked about in 2024, I think a lot of that has continued. It's always evolving.

The report from the FBI in terms of what the cost of cybercrime in the United States has not come out yet this year. But we fully anticipate that the amount of cybercrime will continue to increase as a financial cost year over year. 

I think as organizations can understand and appreciate that they're being targeted by cybercriminals that are interested in their financial resources, not necessarily in their mission.

I think that can help change the mindset. 

I think the use of AI, I think we can see that in how the sophistication of spearfishing messages continues to increase. All that well-crafted language, that's easy now for these threat actors to use and adopt. A lot of the hallmarks that we used to be able to rely on, poorly worded messages, bad grammar, all of that really goes out the window. 

I think the trends that we had seen in terms of account compromises, I think unfortunately, continued unabated in 2024. I'm pulling together our data in advance of our incident report that we'll talk about in April, but it looks like the number of compromised accounts we had is going to be at a similar level to previous years.  

And other things that we talked about, attackers in the middle framework, stealing credentials from accounts protected with MFA, continues. That's why we've made an update to our Cybersecurity Playbook to really encourage organizations to adopt strong MFA methods, particularly for IT staff, for executives, and for finance in particular, as those accounts are really targeted by these threat actors in there, basically working on financial crime, right? Wire fraud. A lot of that stuff really continues. 

The tools in place to help protect organizations, I think, continue to get better.

There are really good protections now for protecting digital identity, having a strong multi-factor authentication. We talked about FIDO keys or using Windows Hello or Platform SSO. Those tools are available.

And then, some of the other acronyms we have up here targeted around email are finally in a place where they're being enforced or required. 

That acronym of DMARC, that is a little DNS record that basically says, “hey, email from our domain is going to come from these places. And if you get an email that says it's from our domain but isn't on this list, quarantine it.” I know a lot of organizations when we're doing assessment, they have that DMARC record. But the flag is set to just report, right? Just give us some information about it.

If you have cyber liability insurance, the automated tools that are checking your compliance are flagging that now and say, “no, it's no longer good enough just to report it. You actually now need to say, quarantine or reject.” Understanding a little bit about how those email support records work to basically provide validation that you are who you say you are when you're sending messages is really important.

On the cyber security side, those are a lot of the trends that we see continuing, mostly around evolutions and sophistication around well-crafted messages. Financial-based crime is still really the ultimate goal for a lot of these organizations. And that's all really being perpetrated primarily through email-based attacks.

And that attacker in the middle framework continues to be very effective. I think Microsoft and Google really still have a lot of work to do to catch up to protect the digital identities so that, if and when a credential gets stolen, that attacker can't use it somewhere else.

Carolyn Woodard: Thank you so much, Matt. We have a lot of resources on cybersecurity on our site. As Matt mentioned, there's a free download of the Cybersecurity Playbook. If you need to get to a foundational level of cybersecurity, that should help you out. 

And next week on the pod, we're going to talk about AI and take some questions and talk about the grab bag of what is available and new for nonprofit IT in 2025.