Is AI Making Enterprise Safer Or Scarier

Big enterprise customers can feel like the finish line: massive budgets, brand-name logos, and the kind of “we made it” credibility that looks great on a homepage. But we’ve seen the other side too, where the same deal becomes a slow grind of checkpoints, approvals, internal politics, and change resistance that can drain a young company’s time and cash.

Alex Romanovich sits down with Stephanie Anderson to separate enterprise romance from enterprise reality. We talk through what it actually takes to sell into large organizations, why enterprise sales cycles stretch into months, and how the real risk is often the cost of change, not the product itself. From CRM-style rollouts to training and adoption, we get specific about why behavior change is hard and how to plan for it so your enterprise's go-to-market strategy doesn’t collapse after the contract is signed.

We also dig into market entry strategy for companies expanding into the United States: how to build business development structure, run smarter discovery, and use partnerships to move faster than hiring a giant sales team. Then we shift to AI in the enterprise, including Stephanie’s recent AI certification and the ROAD methodology (requirements, operationalizing data, analytics, deployment). Finally, we face the uncomfortable question: is AI a threat to jobs and institutional knowledge, or a chance to build better systems without breaking what already works?

If you’re targeting enterprise customers, building a B2B sales motion, or planning responsible AI implementation, this conversation will help you stress-test your readiness. Subscribe for more Global Edge Talk, share this with a founder or sales leader, and leave a review with your biggest enterprise challenge.

Transcript

Alex Romanovich 0:26

Hi, this is Alex Romanovich and welcome to Global Edge Talk. And today, again, on March 13, 2026, we're joined by Stephanie Anderson. Hi, Stephanie.

Stephanie Anderson 0:36

Hi. Thank you for having me.

Alex Romanovich 0:38

We're going to have a very interesting discussion because I've known you always as uh someone who's been on the side of the enterprise. And of course, American marketing and sales talk, Enterprise is this one big colossal company like Charter Communications or SIBO or Cable Vision, you know, multi-billion dollar, you know, huge buildings, big cafeteria, you know, and so forth and so on.

Stephanie Anderson 1:03

Dry cleaner, don't forget that.

Alex Romanovich 1:05

Dry cleaner, exactly. And you know what's interesting about uh the enterprise, and you've spent a lot of time within the enterprise and you know large organizations, is that now we're entering uh um you know a very interesting peculiar time, um uh which is um you know AI driven, artificial intelligence driven and scary. Scary, we'll talk about that. Um enterprise is still a very, you know, very uh it's an attraction uh point, if you will, right? And it's so prestigious, it's so romantic. You know, we're um we're developing a software for the enterprise, or you know, we've done with everything with sales uh you know with small and medium-sized market, and now we're ready for the enterprise. So I want us to talk about that. And I think uh when I thought of you, I thought that you would be the most qualified person to talk about. So let's talk about romance versus reality. And the reality is that the uh prestige and uh sexiness of the enterprise could also be dangerous and the false strategy, right? So the question is are you sure? Are you ready? And uh tell us uh more from your experience, maybe some anecdotes, of companies that have called on you, called on your enterprise and were not ready. Or what does it take to be ready?

Stephanie Anderson 2:20

It's a great question, and it it is sort of romanticized because of big logos. Everyone wants to put someone's logo on their website, particularly by the way, you know, ad agencies want to show that they've done business with big businesses, and it's less about results with that and more about the actual romance of the logo. But I think, you know, when you're coming into a big enterprise, the number one thing, you know, you have to realize is it will take a while to get to where you want to go, no matter what that is. And even if your best friend is the chief marketing officer, it doesn't matter. There is so much structure and so many checkpoints and so many things that, you know, uh boxes that need to be checked before you can actually get that meeting or that introduction or that opportunity that you really need to know that it's gonna take some time. And, you know, that's a lot, there's a lot of checks and balances in enterprise companies, and as there should be. So I think, you know, one of the things is you have to be ready to hunker down and kind of stick to your story and keep telling it repeatedly until you get where you want to go within that enterprise.

Alex Romanovich 3:30

You also told me uh, we had a couple of conversations. You also told me, Alex, the uh the biggest expense and the big risk is not necessarily the product or what's in the product or service for that matter. It could be, you know, software service, it could be what have you. But it's actually the cost and the uh and the risk of change. Tell us more about change.

Stephanie Anderson 3:48

Aaron Powell The Great Change. Well, I think you know, people mistake that maybe the technology is the issue. And I I can kind of I don't want to pick on CRM solutions, but but I kind of will because I think that's something people are familiar with. That is a very structured methodology to tracking your sales, your sales progress, customer information, all of that. And when you introduce something new like that into a large enterprise organization, you're going to get some sort of, you know, there's going to be, I'll call it feedback, but it, you know, it really is sort of resistance. And sometimes that's the most expensive and most challenging thing is that you're trying to change an organization's behavior. You're saying, you know, I love that you keep files in a folder in your car and that, you know, I'm so happy that you know all that information and it's in the trunk of your car, but I need it to also be in this system that basically everybody in the company can see. So it's a, you know, it's quite a transition. And I use that example because I've been through it so many times and the resistance continues. And I think it's not necessarily anyone fearful of that they're not doing their job. It's more that they it's just a change. And change is, you know, frightening, and people have a bit of a problem with it sometimes. So you have to be prepared for that. That it also can be expensive, by the way, because training and reiterating, oh, you know, we we need to do it this way and trying to make it enjoyable, whatever that might be to get the adoption that you you need. So um it's a little tricky.

Alex Romanovich 5:24

Aaron Powell Not only is tricky, it's it could be very slow because uh you know, large ships they have a difficult time turning fast. And for uh for a local company, for a domestic company, that's one thing, but for an international, a global company, I mean, we're in the global business, obviously, it could be even more tricky and more challenging to withstand the six to twelve month uh sales cycle, for example. Aaron Powell What should the company be ready for, especially the ones that wants to be global, wants to come to the shores of the United States and understand not only the industry segment or some of the nuances or what have you, but also understand that that's what they have to withstand?

Stephanie Anderson 6:04

Aaron Powell That's that's a great question because I I've seen, you know, not with everything that we've worked on, but with some things where there's just not very much business development structure to begin with, right? So they're coming, you know, want to come into the US market. It's not like it's gonna be a you know gorilla moment where they're gonna, you know, put a bunch of people on the street and and sell. It's it's largely, you know, just introductions and, you know, how do I get into this company, and so on and so forth. And I think what you need to be prepared for is um, you know, a long path of really figuring out who you can best serve. And by doing that, you really need to understand what the customer's issues are and what that enterprise issues are. And in fact, I think I told you this story, but the discovery process and having a methodology and a plan of attack, you know, I I hate to say it that way, but it kind of is, you know, a plan of approaching a client is really important and strategizing on that. And and now more than ever, with all of the access to information, you know, via AI or, you know, friends, however you gather your story of how you can help that client, that's, you know, you need to go through that process and you need to be prepared for that. The alternative is, you know, pick some great partners. That's that's that's a really great alternative. And um, you know, I was in a role probably 15 years ago where I, you know, was trying to get to market quickly. And we had a great, you know, small business product. And um, I was able to, in under 12 months, recruit seven significant partners to help and to represent our product to the tune of probably a thousand salespeople total. And there's no way you could have gotten a thousand people, you know, really ready in under 12 months that quickly that understood their marketplace, that already had relationships. So now you're, you know, an add-on to their story. So you might want to consider when you're as you're coming to the US or changing markets, even states in the US, because everybody, you know, ha there's different personalities and buying strategies, but consider partnering and finding the right people to align with. That's very strategic.

Alex Romanovich 8:20

I think it's a very good point. We also have the romance of many companies, especially in the early stage phases, especially in B2C segments, in D2C segments, not considering necessarily the B2B side of things, right? And instead of licensing their licensing their technologies, for example, or their products to the partner ecosystem that already has presence, that knows the boardroom, that knows the players, that knows everybody. And um, you know, they're falling in love with, hey, we want our own brand, we want our own thing. Investors give us $10 million or $5 million for branding and marketing and so forth and so on. And uh this is where this is the very important moment of truth where you have to kind of make a decision. What do I want? Do I want revenue? Do I want fame? Do I want a brand? What are my That's exactly right.

Stephanie Anderson 9:11

I mean, what what stage are you in? And what what are the resources that you need to be successful? Who would you like to be aligned with, especially if you're coming from outside the US? You know, what are your top five companies that you want to align with? And then how can you find a way to them? You know, whether that's through help from a partner vendor or, you know, however that works. But I do think, you know, the this goal goes back to methodology, strategy, structure, you know, all these things require, as we have said, you know, the the pilot doesn't get in the plane and just take off. You know, they have a checklist of things they go through every single time, no matter how experienced you are, you go through that checklist before you take off. And I think that's, you know, it's a great analogy because it's it's true for sales, it's true for partnerships, it's true for growing your business.

Alex Romanovich 10:04

And by the way, when we talk about partnership, we're not just talking about company-to-company partnership or product-to-product. We're also talking about very experienced, seasoned people like you and I and others in our network, for example, that are ready to advise, that are ready to help companies uh that are smaller and want to target the enterprise, help them get that experience a lot quicker. And I think that's um that's very important to understand that this is where the multicultural, multi-generational team is going to do much, much better in this environment than the one that says, you know what, we have the best shining object out there and we have the best product and the best feature. When they see it, we're gonna knock them dead, right? Have you experienced something like this?

Stephanie Anderson 10:51

I I mean, I have not experienced that level of a wow factor. You know, I I do think too that one of the things that an experienced or more senior person can help, whether that's a company, like you said, partnership or a person partnership, or having someone on your board or or team, the one thing that they can do is really they it's easy to translate what's what they've been through into the future times or into the current times and the future times. I think people don't realize that, that experiences and most of everything that happens is just kind of repeated. It might be a slightly different language, it might be at a slightly different speed, but it's pretty much happened before. So that recurring theme, it's great to have someone on your team that knows that recurring theme because they know the pitfalls and they know, you know, this might not work out the way we think. And it's not being a big doubter, you know, or down, you know, downer doubter. It's about being, you know, aware and knowing the pitfalls in advance and being able to help guide you so you don't waste any time. I mean, especially if you're an early stage company. I mean, we're kind of making some assumptions here that if you're coming to the US, you're new. But even established, you know, you want to make those alignments with the people that actually know and can, you know, know the turf.

Alex Romanovich 12:06

Absolutely. And of course, that latest uh best uh shining object is artificial intelligence. And recently you got certified as a shout out to Johns Hopkins University expert and Dr.

Stephanie Anderson 12:16

Ian McCollar.

Alex Romanovich 12:18

At Johns Hopkins University. There you go. And um uh let's let's talk about that because now we're kind of entering the the phase of execution, right? So the first uh you know, the first uh phase of this um journey, if you will, hey, are you ready? Number one. Are you ready and you really want to do this? The second one, if you are ready, partner up. Like we, you know, we always say in New York City, we'll always say lawyer up. Well, in this particular case, we say partner up, right? Um but now we're gonna enter the execution. And the execution will say, Oh, you know, if there's no AI in your solution, whether you know you're talking to an investor, an enterprise, or somebody, you have to have at least that in your documentation, right? Tell us about, first of all, tell us about your experience of certification. You know, what is it that you've uh learned in that, you know, through that process, number one. And then let's talk about what we call the innovation paradox. Is AI a threat to the enterprise? Or is AI the um, oh, let's do it, you know, automate all the processes and fire 30% of the people?

Stephanie Anderson 13:24

Um so my experience was was wonderful, very difficult, I would say. And you know, I I'm I've kind of been a math science person coupled with musicians. So I I've always had that art science thing going on, and it can be a struggle. But it but it was a great, it was a great course. It was w really well done. What I will say is a lot of it was repetitive for me. So I hate I don't want to like toot my own horn, but having grown up in AT ⁇ T Bell Lab era, you know, till now, I mean, I got to go to MIT and you know, go to the Unix lab and see how to create a user interface that was actually better than the VI editor of the time when you had to type in, you know, you had to do an email and VI editor. I mean, it was crazy. So I, you know, go back to that time and you know, the machine learning, all of that I've watched evolve as my, you know, my roles at Avaya with call centers and all this, you know. So I felt very comfortable, which was surprising. And the other thing I would tell you, and it's great information, is the structure that they use is uh road or O A D. And it's it's requirements, which would mean you need a domain expert, it's operationalizing data, which would mean you need a data engineer, it's analytics analytics method, data scientist, and then deployment, which is one thing that I think is very cool, which is kind of having this visual scientist, visual expert that can take what's going to happen, what are we going to change, and turn it into a visual account of that. So the road methodology, again, is a guideline that Dr. Ian McCullough repeatedly said, you know, if you're following this, you won't mess up mess up. You'll have a successful AI project. So I think that's excuse me, part of the part of the uh class showed me again that having a method and having a process is extremely important. That coupled with communicating, I would say. Those two things. Communicating it throughout the organization. Make sure, you know, people need to know what's going on.

Alex Romanovich 15:28

But do you think AI in in um most of the enterprise organizations today? Do you think AI is a threat? Or do you think there is a certain level of, oh great, you know, I'll have a chance to learn something new uh if I'm still here? Uh in other words, if it's a publicly trading a publicly traded company, yes, uh the the um um the thought of um automating and replacing is there with the executive team, obviously. But if we're going to follow the rules of, or if we're gonna follow the methodology of we need the seniors, we need the mid-level managers because they have the knowledge, they have the method, right? If we're gonna turn the method into a product, we're gonna turn the knowledge into something tangible that we can use with our customers, yeah, and so forth and so on. Then we have to be very careful about those, right? There's actually even a notion right now within the software development community that um uh and the services community that the juniors unfortunately are going to be the first ones on the chopping block because they still don't have that knowledge, institutional knowledge, if you will. However, they may have the um the knowledge of the tools. They may be the the easiest one to adapt and so forth and so on. So there's a very tricky time right now that we that we're entering in terms of is this a threat or is this a blessing?

Stephanie Anderson 16:48

I would comment your Andrew Yang um post that you had basically also said it's the unemployed that are being cut before they're employed. So it's people like, you know, as a mother, my son, you know, who's graduating from college in data science, you know, that's a that's scary and business analytics. So we'll, you know, we'll see what happens. But yes, I mean, I think that the institutional knowledge that is in companies that it is is not really measured. And so you talk about the people that are in roles today that have all of this um, you know, intellectual property basically floating around and institutional knowledge. What's gonna happen with that? That what is what makes companies run, by the way. Technology is great, but it's the person that like basically plasters their body in front of the customer and saves, saves the way the company looks. That's reality, honestly. I mean, nothing is as smooth as as you'd like it to be. And it's not really any person's fault or any system's fault. It's just things happen. And if you could predict everything, you know, you'd have a bigger title. Let's put it that way. You'd have the ultimate title. So I I do think that, you know, that institutional knowledge needs to be cared for. The in the intellectual property of the company, you know, somehow needs to be cared for. So I think, you know, yes, is it a threat in some ways? Definitely. You know, definitely AI is a threat to some roles. Will it create new roles? You know, don't I don't mean to demean AI, but I remember when everyone said that email was going to eliminate paper. And it's the furthest thing from the the truth because everyone printed their emails. And I would tell you that AI is probably creating additional paper because people are printing things out that they're learning from AI because they want to take it with them to a meeting or they want to whatever. So I I think we need to understand that while it is a threat to certain roles and hopefully they're the things that most of us we don't really want to do anyway. What was the joke about, you know, I d I want to have AI clean my house so that I can go exercise or I can, you know, that that's what we really want. So hopefully we'll head in that direction and no more vacuums for us.

Alex Romanovich 19:02

Aaron Powell And actually that's a very good point because you've spent a lot of time with the services organizations uh within the enterprise and all the way down to maintenance crews and folks that would install cable and so forth and so on. And this is where, you know, if you're going to replace those systems or if you're going to modify those systems, right, you have to be pretty damn sure that you're not going to disrupt that particular method, that particular flow when you and you know, which is fairly complex because you have to work with outside contractors, you have to work with the SKU numbers, you have to work with so many different variables out there, right? And as we know, AI tends to hallucinate sometimes and so forth, right? So imp to implement even a system, not to even replace, but to augment or to automate or to enhance, it would take quite a bit of time. Speaking of time and speaking of being ready to do something like this, you and I talked recently about the uh the readiness, right? The the whole concept of are you ready and how can you check if you're ready? AI certainly can help with that. Right. But you know, you may have to go as a company, you may have to go through some level of assessment or some kind of an assessment. I know you don't like the word uh discovery. Yeah, no offense to the McKinsey word, right? And right, no offense to anybody, uh, but discovery is a uh is something that folks do not like because uh you know they assume that you have to you already discovered something about me, right, as a customer. But as a founder of an international company or even domestic company, you have to kind of assess whether you're ready, not ready, uh what exactly are you ready for, what should that conversation look like, and so forth. So you have to really create that um that infrastructure to be able to constantly uh be on top of those things. If you have to give one piece of advice to companies that are entering the enterprise or considering the enterprise, want to self-assess themselves or um you know at least be be on the lookout for those types of uh issues and in the world.

Stephanie Anderson 21:10

I think we've talked about it a bit, which is structure and the checklist and preparation, um, and basically flip the discovery on yourself, you know, before you go to the customer. Discover why you want to be in with that customer. Don't just sell to them because they have a great logo or it's gonna be a $30 million, although that's a perfectly good reason, but really understand how you can help them. The couple of things that I would say is, you know, preparation we know now is even easier with AI. Be careful though, because you know, you do need to make sure that things are in the context that you, you know, you are reading them to be in. Um, and also, but but just you know, going through some sort of an assessment and being ready, I think is very, very important for your company and set your own methodology. Say, you know, it's got to go, you know, we've got to go through these checkpoints. I remember running a team that was a combination of services folks, of product people, of salespeople, and it was a margin review team. And we would get together on a weekly, usually weekly basis, depending, unless it was an emergency. And generally speaking, it was a sales team that was selling to I'm gonna use American Express as an example, selling to American Express, and they wanted Wanted a discount on the second year of maintenance or something service or something like that. And so everybody's in the room, you know, figuring out can we do this? Is this a viable thing for our company? Is this a good decision? I loved that. It was, I mean, it was kind of grueling and a little bit, you know, there's a little some arguing going on, but we were behind closed doors. It was a great way of figuring out are we ready? Is that business we really want? Are we willing to make these cuts to get that business? Are we willing to possibly let that be known by others? You know, that could that could be something that gets out that people other people find out about. There's there's just a lot of things you need to think through. So if you can't get in a room with your people and you don't have a methodology, you know, you're just gonna show up with something in your hand and you know, you're kind of, in my opinion, you are putting, you know, fate in the hands of the customer instead of in your own.

Alex Romanovich 23:19

Great advice. Great advice. Stephanie, thank you so much for being with us. And uh, I know this is not the last time we're talking about this topic and so forth. We wish you lots of luck and uh we uh are gonna be seeing you out there. And uh I think your son is a very lucky young young man because he has a mom who has got all this amazing experience. So even if he is uh considered a junior within the enterprise uh environment, he's got you behind him.