Ready.Set.Midmarket! Podcast: Midmarket CIO Priorities for 2026 - Why AI Can’t Move Faster Than Your Data Security
In the latest episode of Ready.Set.Midmarket!, Samara Lynn, senior editor of MES Computing, sits down with Ron Reiter, CTO and co‑founder of Sentra, to break down what midmarket IT leaders must get right before rolling out AI at scale.
Reiter makes a clear case that AI doesn’t just improve productivity—it magnifies existing data security gaps. When organizations enable tools like Copilot or enterprise AI assistants without a solid data access governance model, AI can instantly surface sensitive information that previously went unnoticed.
The conversation explores why data visibility has become one of the most urgent CIO priorities for 2026, how CISOs and CIOs can align instead of clash, and why midmarket organizations can’t afford to “lock everything down” in the name of security. Instead, Reiter argues, leaders need technology that enables teams to run fast and secure at the same time.
🎧 Watch the full episode to hear:
- Why AI acts as an accelerator for both productivity and risk
- How midmarket IT teams can prepare decades of data for AI without massive headcount
- The one metric CIOs should stop relying on in 2026
The full episode can be watched on YouTube and heard on Spotify and Apple Podcasts.
Previous RSM! episodes are here.
Transcript
Samara Lynn
Okay, so we'll get started. So I just want to thank you and Welcome you to another episode of Ready Set Midmarket! the podcast for midmarket IT senior leaders. I'm Samara Lynn, the senior editor of MES Computing. And usually I'm joined by my co-host, Adam Dennison, the vice president of midsize enterprise services at The Channel Company. But Adam is prepping for our big event in Florida next week. We're having the MES IT Security Summit. So he's got a lot on his plate right now, but we didn't want to miss the opportunity ⁓ to speak with you, ⁓ Ron Reiter You're the CTO and co-founder of Sentra. And I'd to kick off by just having you tell us a little bit about yourself and telling us a little bit of the audience about Sentra for those who don't know.
Ron Reiter
Sure, thanks. So my name is Ron. ⁓ I'm the CTO and co-founder of Sentra, ⁓ a data security platform company. So Sentra basically is a tool to look for sensitive data and to ensure that it is secure. ⁓ We help organizations build their data loss prevention programs, ⁓ achieve compliance on data regulations, data access governance and so forth. We're about 100 employees. We've raised over $100 million. We have been founded in 2021. So I have a few of my co-founders. They used to be very senior officials in the Unit A200. One of them was actually the head of Unit A200. And that's kind of where we all met.
Samara Lynn
That's really interesting. And you know, this topic is about midmarket CIOs priorities for 2026. And we've done a lot of coverage on this subject, Ron. And one of the things that keeps coming up from, you know, IT leaders like yourself and thought leaders is that you cannot implement. One of the main priorities is implementing AI. I mean, let's get that out of the way. But you can't implement AI without having a good solid data strategy.
So I think that's where it's an ideal conversation for us to speak. And as you know, know, CIOs right now, they're under pressure to prove ROI from their AI. They have to reduce their risk and they have to simplify their tech stacks. Out of those, what's right now, what is the first A in ABC that a midmarket CIO needs to prioritize to launch a successful AI project in your opinion.
Ron Reiter
Yeah, that's a great question. So I think, you know, we've noticed that in the last couple of years, we've turned into an AI security company. We weren't when we started Sentra we weren't starting an AI security company. We were starting a data security company. So what happened in the market is that it's an interesting thing with AI ... when an organization wants to use AI responsibly, the number one thing that pops up right away is that AI is basically an accelerator for how your data security program should already be ⁓ applied. What I mean by that is when you're a CISO, right, and you care about your data security program to a certain extent. Now there's suddenly this amazing technology that can ⁓ mine your data in the best way possible, which is huge for productivity. But it's also a very, very, very big risk from security because it basically underlines it. It really emphasizes where your data security is not correctly set up. So, so in the sense, you know, let's, let's take an example. You know, there might be in an organization, some, any organization, right? Sometimes people would have maybe a public document to the internet or maybe a document that is shared with everyone in the organization that has salaries of employees, right? Or something like that.
Obviously, sense of data, but nowadays it's not really an issue because if you don't have the link to that document, people don't really notice that it exists. But suddenly, now there's this thing called AI, and you activate it, and it goes and indexes all of your corporate organization according to the permission map and the access governance that you set up originally, which you should have done that correctly.
Now, suddenly every attacker can ask a bunch of very, very simple questions like, give me all the salaries of people in the organization, right? A very simple question. You can ask 100 questions like that and your AI ⁓ agents will just directly go and collect that information from everywhere around the organization and that would be an immediate threat to the organization just because someone enabled Co-Pilot, right? What I'm trying to basically say here is that if you want to enable AI responsibly, you have to have your data security program also set up in a way that is perfect, right? You have to make sure that no document is accessible to people who should not have access. You to make sure that no model can read information that it's not supposed to. And that's a data security problem, right?
Samara Lynn
RLet me ask you this, and I'm just going to off the script a little bit, just because I've been in IT for a lot of years and now I'm working in this capacity more as an end user. We got license for AI to use throughout our organization. One of the things I wanted AI to do was to help me manage my folders and my inbox, but it doesn't have permissions for that. Is there a way when you can lock down AI and data too much that it inhibits your employees?
Ron Reiter
You know, that's really what the strategy of the CISOs is now right now. That's what they're doing there. They are because they don't have. Right. So if you don't have a tool, I mean, I'm sorry for overselling here, but if you don't have a tool like Sentra, then sometimes it will be easier for a CISO to say, all right, I'm just locking down all of this environment, no AI for anyone. And that's it. That's how I'm going to deal with it, because I know that there's sensitive data there.
That hurts productivity, right? If you want to enable productivity and at the same time, make sure that your organization is actually secure, you have to have a tool that knows how to differentiate between sensitive data and data that is something you want to ⁓ make available for everyone in the organization. And that's what Sentra does, right? So we're able to classify sensitive data in multiple ways and make sure that it's tagged accordingly so that ⁓ it won't be available to those AI models and potentially a data breach could happen.
Samara Lynn
Because really now it used to be data is the new oil. Now it's like data is the new attack surface, right? Because you're letting all these AI components into your organization. Is that why data visibility should it be one of the top CIO priorities this year?
Ron Reiter
For 2026 for sure. Wwe were always, you know, trying to echo to the world how data security is a big problem mostly because of how cloud is adopting, right? And so the adoption of the cloud was very apparent in the last five years. We were seeing a lot of organizations go and migrate a lot of data there. And then the data security posture needs to be maintained. But I think
AI has been accelerating this, you know, 100 times because everyone is trying to use AI. Everyone is trying to, you know, hook it up to the cloud. Not only, right? And then you have to get your data security program ready by the time that the AI program is ready. So that's kind of what we're seeing across the market.
Samara Lynn
So, and again, you know, I, you're obviously you work for a vendor and I know you can apply this to your company, but just generally overall, broad. I'm in midmarket IT director. got a staff of like five to 10 people. have a limited budget. My CFO, my CEO, they're like, we need this AI project implemented ASAP. How do I go and collect, even though I'm a midmarket organization,
How do I go through decades of data, cost effectively and get it prepared for an AI project?
Ron Reiter
That's a great question. So we sell to both enterprises and midmarket companies and we see a lot of difference between those two, right? So enterprise companies usually have data teams that go and have, you know, they have a role of classifying all the data in the company for multiple use cases and this is what they do, right? So we go and solve a technical problem there. But for midmarket organizations who don't have any data security program and need to be prepared with AI,
So we're basically giving them a very simple solution, which is data loss prevention solution, right? A DLP, a cloud DLP solution. And we're just saying something very simple, right? You need to have a tool that will go and classify all of your data wherever it is, right? Let's say I'm 365, right? Once you classify all of your data and you understand it and you know what is sensitive and what is not, what Sentra will do or you know, basically any data security platform is it will tag the data automatically and make sure that that piece of information won't be available to those AI models, right? So in that sense, you don't really have to have a person that is working 24 seven, resolving issues, you know, reading tickets, trying to figure out how to set up things, right?
It's basically a tool that you need to identify the sense of data and block it from going in continuously to those models. That is one example, right? But that is the ultimate problem that the CISOs in 2026 are hitting right now when they're being told, hey, we want Copilot hey, we want AI, we want Gemini, we want to be productive, and we want to put this on our corporate data, maybe ChatGPT Enterprise or whatever, right? And we want to do it responsibly.
Samara Lynn
Right. So, Sentra, you're more around the data security and sometimes you probably work with some quite a few CISOs, security officers and executives. What we found in some of our coverage is sometimes there is friction between the CIO and the CISO. Their goals aren't often in alignment. Is that something you've seen with customers you've worked with, like the CIO and the CISO have different goals and some clashes and how have you resolved that?
Ron Reiter
So I think there's different goals of CIOs and CISOs mostly because CIOs usually care about getting the ⁓ organization more productive, whereas CISOs have basically the role of making it less productive but more secure, right? And that's really what it's all about, right? If you look at one side saying, hey, I wanna make the organization more productive,
Right, that's their goal. Not only the CIOs, usually it's sometimes the R &D, sometimes it's the chief data officers, many, many different roles. But there's always this person who says, I want to enable AI and I want to enable the organization to run faster. And then there's always a balance, right? Those checks and balances between the governance, risk, compliance functions that their goal is to make the organization more secure. And they always, always will come on the expense of productivity. Right.
And you want to make sure is that while you make your organization more productive, you want to make sure that it stays as secure as it is productive, but at the same time, you don't want to hurt productivity, right?
Samara Lynn
It's like this kind of catching up back this balancing act, you know, between being progressive and you know, productive and staying secure and reducing risk. It really is kind of like to me that in a nutshell is a priority for CIS for CIOs in 2026. You know, how do we stay competitive and stay secure?
Ron Reiter
Exactly so and the way we see it is that we need to you need technology. The customer that our customer right now understands nowadays that with technology it is possible to run both ⁓ fast and secure at the same time, right?
Samara Lynn
Well, I know we are pretty limited at time. I ant be respectful of time. And we're just so happy to have Ron Reitner. Ron, am I saying your last name correctly? Ron Reiter, my apologies. You are the CTO and co-founder of Sentra, which really specializes in data security and has this AI forward approach to that.
Ron Reiter
Reiter
Samara Lynn
So I'm going to introduce before you wrap up, a lightning round, which is going to come to surprise as Adam when he comes back. But I want to do like a just quick, quick questions for our guests. What I would like to ask you is what is the one metric that you think CIOs in the market mid market should stop relying on in 2026?
Ron Reiter
should stop relying on?
Samara Lynn
stop relying on.
Ron Reiter
Wow. So I think 2026 is a transition between AI eras, right? And I think they need to not optimize on choosing the right tools. I think the tools are changing so fast that it really doesn't matter. Just get something, try it out. Don't try to over optimize. Whatever works, works. Whatever doesn't, you know, doesn't.
Samara Lynn
Well, and then leading to that, what is the one question that you as a vendor, successful company, what is the one question do you think midmarket CIOs who should ask you guys more?
Ron Reiter
Well, I mean, it's a cliche" how do you run fast while staying secure?
Samara Lynn
Okay, alright. Well, we'll leave it with that then. ⁓ All right. Well, ⁓ I want to thank you so much, Ron. Thank you very much for your time and definitely tune into our episode with the great information for our midmarket CIOs with our guests, the CTO and co-founder of Sentra. And thank you all for joining us today. Thank you.
Ron Reiter
Thank you for having me.