A healthy culture of AI experimentation and fluency in the workplace doesn’t happen under pressure. It needs room to breathe.
So Andy Sen, CTO and co-founder of AppDirect, opened up that space by giving his 1,000-person team access to an AI playground and then he … stepped back.
The results: HR built a custom recognition platform. Finance automated workflows. Marketing created chatbots. The entire organization built with AI from the bottom up rather than the top down.
In this episode of Keep Moving Forward, Andy shares why fear of AI fades when people get the opportunities to test it out for themselves, how celebration drives adoption better than mandates, and why it’s important to start small if you want to see big changes.
Fear Loses Power When AI Gets Practical
Once people start using AI, the fear of being replaced starts to fade. What takes its place is curiosity — about how much faster, sharper, and more focused their work can become.
Andy hears fewer concerns about job loss than he did a year ago. That shift, he says, comes down to the direct result of responsible and playful exposure to AI. “If you use AI in your role, you’ll very quickly come to the conclusion that it’s nowhere close to taking anybody’s job.”
What it does take off your plate: the boring stuff—refactoring code, updating statuses, repetitive workflows. What it doesn’t touch: strategy, system design, human judgment.
He compares it to when Excel first showed up in accounting departments. It changed how people worked, but there was still plenty left for people to do.
How an AI Playground Unlocked a Culture Shift
When AppDirect launched Devs.ai—a no-code platform for building AI agents—it wasn’t a mandate. It was an open invitation. Everyone got access. What they did with it changed everything.
People who’d never built software started experimenting. HR built a custom recognition platform. Finance automated manual workflows. One non-technical employee even shipped a mobile version of Devs.ai over a weekend.
So how did this company go from having siloed departments with only a few capable of developing software, to having an HR team that can safely automate their own busywork? The secret lies in radical trust and empowering everyone to be an innovator. "Let's see what people are doing, see the projects which are the most successful and celebrate them," Andy says.
All they had to do was call out the innovation and create the psychological safety necessary for others to try. "We have pockets of people, pockets of innovation across the company in every department," Andy says. "I'm not just talking about software engineering. We've got people in the HR department, people in finance and marketing."
With a foundation of trust and a bias toward action, the barriers to building came down—and the creativity took off.
Progress Starts with One Test at a Time
Andy’s advice to leaders is straightforward: Start small. Try something. Try it fast.
“Dip your toes in it,” he says. “Try something quickly.” The goal isn’t to force an enterprise-wide rollout. It’s to build a proof of concept, gather feedback, and adjust.
To get ahead, don't chase what everyone else is building. Focus on what makes your company different. "In the age of AI, your data and your processes are what's valuable. That's something no one else has.”
Not every experiment will land. AppDirect’s early chatbot efforts stumbled—open-ended prompts confused users and slowed adoption. But even the misses taught them what to do next. Progress came not from one big win, but from a rhythm of fast tests and fast learning.
“Everything keeps changing, and AI is simply accelerating that rate,” Andy says. The job isn’t to build the perfect system. It’s to build a team that can keep moving forward—fast, curious, and unafraid to try.
Transcript
Andy Sen:
Everything keeps changing, and AI is simply accelerating that rate. So you have to have that mindset of thinking the way that your business and your operations worked in the past is probably not going to be the optimum way in the future. So be open to new things coming in, have a process, whatever it is, of being able to evaluate new information, and be able to act on them quickly is, to me, the idea of keep moving forward.
Gemma Versace:
Hey everyone, and welcome to Keep Moving Forward, the podcast from X-Team for tech professionals who are passionate about growth, leadership, and innovation. I'm your host, Gemma Versace, chief customer officer at X-Team. In every episode, we sit down with leaders who are redefining how technology teams work, grow, and lead — people who understand that performance begins with connection.
Today, I am joined by Andy Sen, CTO and co-founder of AppDirect. Andy has spent his entire career building online marketplaces and commerce platforms from IBM's early internet commerce group to Salesforce, Walmart Labs, and now AppDirect. As the company's first employee, he has helped it grow into a global organization with more than a thousand people across multiple continents. Andy brings a grounded perspective on what it really takes to lead distributed teams and drive innovation at scale. He shares how keeping teams regionally connected strengthens collaboration and how clear ownership helps people move more quickly and confidently. We also talked about AppDirect's Dev.ai playground and how giving everyone access to AI tools sparked unexpected innovation across the company.
Andy explains why celebrating these experiments matters, how non-technical teams are building real solutions, and what happens when people feel free to explore. Throughout our conversation, Andy reminds us that progress comes from staying curious, trying things quickly, and learning from what happens next. It is a thoughtful look at how leaders can guide their teams through rapid change without losing sight of culture, connection, and ownership. Let's get started.
Welcome, Andy. Thank you so much for joining us today.
Andy Sen:
Thank you, Gemma. It's great to be here.
Gemma Versace:
Awesome. Let's get straight into it. So let's start by having you introduce yourself and your career journey, having worked for some really big logos such as Walmart and Salesforce, and now CTO at AppDirect, leading the large global team. If you can give us a little bit of background as to what your career journey has looked like to date.
Andy Sen:
Yeah, my career, I've essentially been doing the same thing in different contexts and different companies. I graduated in the late '90s when the internet was just becoming big in terms of commerce, and my first job out of college was at IBM. They'd just started this new group around internet commerce where I started, and essentially, every one of my roles ever since then has been with some aspects of marketplaces or commerce online.
I've worked at IBM, I've worked at smaller startups. I was at Salesforce, where we were part of the AppExchange, which was the first online marketplace for applications. As you mentioned, I worked at Walmart Labs, and then I was very early on, I was the first employee at AppDirect, and that started in 2009. We're a subscription commerce company where I'm the CTO. And I've been there for the last 15 years, seen a lot of different changes in the industry and have been part of this great journey at AppDirect, as we have grown to a company with over a thousand employees now, with operations all over the world.
Gemma Versace:
Yes. What a fantastic opportunity you've had at AppDirect, being one of the first employees, now over 1,000 strong globally. That's absolutely amazing that you were there from inception. Your team is globally distributed, as you've just said, across North America, South America, parts of Europe, and India. How does this geographic and cultural diversity play into how innovation and AI is adopted at AppDirect?
Andy Sen:
Absolutely, and at AppDirect, we've had a globally distributed team for a long time. Well, well over a decade now. So there's been many lessons learned along the way. Time zones are real, and it's always a barrier that needs to be overcome. One of the things that we have learned is to not distribute actual teams, or try to avoid doing that, in the people you work with on a day-to-day basis. It's really important to have them in the same geographical location or at least in the same time zone.
So what we've tried to do is to have entire teams who have ownership over a certain product, and try to have all kinds of cross-functional people in that location, whether it's engineers, QA people, product managers, design, all working together locally. And then the coordination at a global scale comes up at a higher level. So each team owns their own work, and the portfolio planning and the overall company roadmap is organized centrally.
Gemma Versace:
I really love that. I love the thoughtfulness and deliberate nature of having teams regionally close to each other so you can garner more of that collaboration and engagement. I think that's a really great idea and also leads into, I guess, a little bit of the next question, too, talking about how you've structured the team. You've also both structured top-down AI initiatives, as well as organic bottom-up efforts happening simultaneously. How do you manage this balance without stepping on innovation within the teams?
Andy Sen:
That's a great question. Like many other companies, we have a top-down or strategic use of artificial intelligence, where these are features baked into our product roadmap. They have a team or multiple teams working on them, and over the last year and going forward, we are incorporating more and more artificial intelligence capabilities into the AppDirect platform.
But along the way, one of the things that we have seen is this idea of artificial intelligence projects coming up from the bottom up. And what we have done around that is we created this digital playground, it's called Devs.ai. It's free for anybody in the world to go check out, where anybody — you don't have to be technical, you don't have to know how to code — you can go in and create your own chatbots. And more than chatbots, you can create your own AI agents and so forth.
And what we did is we just opened that up to everybody within the company, and the results have been pretty unexpected and great, that we have pockets of people, pockets of innovation across the company in every department. I'm not just talking about software engineering. We've got people in the HR department, people in finance and marketing, all just organically using artificial intelligence to make their life better. They might be putting in chatbots, they might be creating tools, they might be creating ways to just learn more for themselves, for education. And all of that is organically happening everywhere in the organization.
So from an IT perspective, what's great is we've created this playground. We have put in certain guardrails so that people can use only LLMs, which won't leak data. We've put in guardrails around pricing and costs so that you don't inadvertently spend a million dollars on your pet project. And then we have the visibility to see what everyone is doing. And the great thing about that is the attitude hasn't been about, "Well, let's try to block people from doing things." It's more about, "No, let's see what people are doing, see the projects which are the most successful, and celebrate them."
So it's also a cultural issue across the company that we've had company-wide hackathons, we promote people in terms of giving them visibility, the people who are doing great AI projects. So it's transformed not just the way we use technology, but in a way, the culture of the company, as well.
Gemma Versace:
Yeah, thank you so much for that detailed answer. And also what a exciting journey to be on where traditionally, within teams, it is very much more of the IT or the engineering teams that are the ones playing around more so with the AI tools and creating new opportunities and development. But the way that you're engaging both non-IT engineering as well as the IT and engineering teams, that's absolutely fantastic.
How does empowering every employee to experiment with AI, own their results, and scale successful ideas strengthen this value? And, I guess, what specific ownership behaviors have you seen emerge through the teams as a result of this?
Andy Sen:
Absolutely. So again, this has been a core value of AppDirect, though long before we started doing anything around AI. In fact, the first question you asked me about, like the geographical dispersion and how we manage global teams, ownership plays a huge part in that, as well, because we want teams dispersed geographically to own particular aspects of their product.
Now, when it comes to AI and being able to build your own tools or create your own agents with the AI, there isn't a top-down mandate saying that you have to build an agent or you have to use AI. But it's teams have ownership over their outcomes, and we've provided them with tools, and they realize that they can get their outcomes better, faster, be more efficient if they use AI. And even within that, it's kind of organic. There are some people who are more of the tinkerers — that they like to play around with something new. And just organically within a team, there are some people who will just be like, "Hey, this sounds interesting. I'd like to try it. I'd like to build things with it."
And so the team organically figures out that they need to use AI to do their jobs better. And again, organically figures out who's the person on the team that will take the lead. And there's many examples, and here's a simple one. We have an employee-recognition software within the company. It helps us, if you see a coworker doing great stuff, you can recognize them, you can applaud them, and then the whole company knows that they're doing a good job. And we used to use a commercial software for that, but then our team figured out that they can just build a tool using AI — these are non-technical people, not engineers — to build a tool internally, which does the same thing. And again, it wasn't a top-down mandate, it just came up through the ranks.
Gemma Versace:
What a fantastic example of exactly how your program of giving ownership and empowering and creating this wonderful playground, as you mentioned, to be able to see and articulate some of those really successful results. And the tangible benefit that is getting derived from this is just such great examples and further validation around Devs.ai creation being such a wonderful tool for AppDirect and potentially others out there, as well.
And one of the things that you were talking about then is seeing how some of the different people within the different teams, whether it be technical or non-technical, are really rising to the challenge. And how you've got the tinkerers, the ones that probably a little bit more like me, that would need a little bit more help and a little bit more experiencing, getting a little bit more confident about creating in Devs.ai.
What other things have you learned about the types of people that really are thriving in an AI-enabled environment? You mentioned before that there's the natural leaders that are stepping up. And there's, I guess, the different buckets of people, with the tinkerers and the ones that are really leading. But what have you specifically learnt about how to embrace, helping to keep people learning, and helping to keep them very much engaged and thriving in an AI environment?
Andy Sen:
That's a great question, and I think the answer to that is really, it's not a technical answer, it's a cultural answer. It's having a culture where exploration of AI in general is encouraged, and we do that with many different things. I mean, we have company-wide hackathons where people are encouraged to use AI, but the other thing is using the visibility that we have over AI initiatives to give positive reinforcement. I mean, you hear stories of IT departments trying to block AI or trying to monitor how people are using AI. And we have just a radically different approach.
When we have visibility over AI initiatives, we use that to celebrate them. So if someone's doing something new and innovative, we encourage that, we hold them up as an example, saying that if your peer or your coworker who's just as technical or non-technical as you can do it, why don't you try it, as well?
There's no downside to it. There are people who frankly are not at this point in the technology curve too comfortable with AI. They don't want to build their own AI, and that's fine, as well. But the idea is to just give or create an encouraging culture. And as these advances happen, and these AI advances are happening so quickly, at an exponential rate, at some point, if people are aware of what's going on, they might get to that point in the curve between complexity and usefulness to say, "Oh, yeah, this is good. Now, I'll step into the water."
Gemma Versace:
That's so cool in being able to really just reinforce that it's a safe place for people to be, as you said, dipping their toe in, feeling more comfortable, but also by celebrating the wins and really highlighting the benefits and the individual opportunities, just personally, of people creating something. Versus the example that you gave about the creation of the new talent performance platform. The opportunities are really endless, both at opposite ends of the scale, as well.
So you've mentioned that a lot of the AI development is now working alongside the software engineering teams and that there is a lot of advancements and some work now that the developers are able to rely on AI to help. How do you keep your team motivated and not fearful that one day AI is going to take their jobs?
Andy Sen:
Well, I almost hate to say it, but if you use AI in your role, you'll very quickly come to the conclusion that it's nowhere close to taking anybody's job, and I don't see that happening ever. AI is a tool, and it's a tool which makes you be able to do your job better. And frankly, and this is not just software engineering, we see this on our operations team, as well. The things which AI help you with are the things which are the most tedious to begin with. Refactoring code, updating statuses, all kinds of things which took a long time, but just wasn't very effective.
The actual planning, what you want to do, how you want to do it, what is the overall strategy? At this point, AI doesn't come anywhere close to doing that. And I think to be fair, a lot of people had that fear when we started this journey, but I think the more exposure you have to AI, the more people realize that these fears are just unfounded.
It's like saying that, I'll throw another analogy out there. It's like an accountant 40 years ago being shown Microsoft Excel. I mean, yes, this can do calculations so much faster than a paper and pencil and a calculator, but Excel is not going to take away the accountant's job. And I think across the board, we are seeing that with AI. Just anecdotally, I hear a lot fewer concerns or complaints about AI than I did, let's say 12 months ago. And I think with familiarity, people realize it's just a great tool for their jobs.
Gemma Versace:
That's a really interesting point. I did hear somebody not long ago talk about answering this question to say that it's an opportunity with the development of AI that people shouldn't be worried about it taking their jobs. It means that people are going from sitting in the orchestra as maybe a flutist or playing the clarinet or playing the trombone to using AI to actually expand into being the conductor. Because you start to really be able to get all of these wonderful tools in your tool belt that you, then, are actually just expanding and enhancing your own individual productivity and output, as well. And I thought that was a really cool analogy to use.
Andy Sen:
That's a fantastic analogy, and I'll give you an example of that. The Devs.ai platform, like we built a platform internet first and then we set up — and it was a particular, it was a technical person, but not a software developer, in our company thought, "Well, why not make a mobile version of this? We do so much, so many of our activities on the phone, so can we have Devs.ai on the phone?" And this was not a software developer, it wasn't a designer, either. And with experience in software development, I mean, you know what a mobile application, the complexity to build it. You need a design. It's different from the web design. You need to actually code it. It's done in a different programming language than the internet. You need to test it. There's a whole workflow involved. Using AI, this one person in our company, essentially over a weekend, built a mobile app, or a mobile version of Devs.ai. So it was just done.
So this person acted as the product manager, acted as the designer, acted as the software engineer, acted as the QA. As one person, they became the entire orchestra, to use your example. Now, was it a fully finished product that could be released to the entire world in a weekend? No, and that's where you still need the skills and the experience to take it to a polished, releasable product, but that one person could just go from an idea to a very advanced prototype just by themselves. It would've been impossible even two years ago.
Gemma Versace:
What amazing examples of just such great innovation coming out of your teams with the Devs.ai platform, as well as without. I mean, it seems like you very much have created such a wonderful culture of innovation and excitement and such a “have a crack” or “give it a go” attitude. I just think that is so powerful, and it's a nice segue into my next question, as well, because you've talked about a lot of the different initiatives and opportunities that you're giving your teams to be able to play in the playground with AI.
As a leader during such a boom in this AI era, were there any learning moments of initiatives that didn't go as expected? We've talked a lot about what went in the win column and all the really fun, great things. What potentially didn't go as well as you were expecting or hoping?
Andy Sen:
Yeah, I mean, this is obviously a very new technology. So I'd say one thing which we've found out, everyone was introduced to AI with chatbots first. And so the almost immediate impulse was, well now, instead of the user interface, let's make a chatbot. Let's show that chatbot to our customers. If they have any questions, they can go through the chatbot. And I would say that had very mixed results. Chatbots are very useful in a controlled environment, let's say within your own company, but introducing a chatbot to the outside world, a more uncontrolled environment, users are more used to having a web or a mobile interface. It’s challenging. A chatbot doesn't have enough guidelines or guardrails for users to be able to effectively do what they want to do.
And we saw that, and we had to evolve beyond that in making sure that we are now using agents with guardrails. That they can take people through the journey as opposed to just giving a blank prompt. We started incorporating pieces of user interface within the AI chat interface. So instead of just coming up with a wall of text, there's actual UI elements, buttons, dropdowns, things like that, where users can interact with. And that seems to work a lot better than just, “Here's a chatbot, the universe is wide open, ask what you want, do whatever you want”. And I think that's definitely something that we have learned and are taking forward, as well.
Gemma Versace:
Yeah, great. Thank you so much for sharing that because it is important that other tech leaders that are looking to you, that is leading such a large team, such a large global team, but also for all accounts, a very successful team with a lot of the developments and innovations that you guys are creating. But it is also really important to really talk about what didn't work, why it didn't work, and as you said, do that deep dive and do that autopsy, and then create the corrective action to make sure that you and your team are learning from those, I wouldn't say failures, but for some of those challenges that come up, as well.
On that, as the leaders that are just starting in their AI journey, and especially those that are really wondering, “How am I going to bring my team on this journey? How am I going to empower them? How am I going to excite them? How am I going to engage them? What advice would you give them?”
Obviously, you've come from, as you've mentioned, the last 12 months in particular have been quite a transformation period for the adoption of AI and some of these wonderful, exciting programs and initiatives. What advice would you give to that CTO who's sitting there at the very start of their AI journey? What are, I guess, the top maybe two or three things that, from your experience, but also from your understanding, what advice would you give them?
Andy Sen:
At AppDirect and even for me personally, we like iterative development. We like to do things quickly and get feedback on the results and iterate based on that. So based on just that philosophy, what I would tell anyone starting the journey is to dip your toes in it, try something, and try something quickly. I wouldn't force people to go down some big AI project and mandate, “This is the new workflow that we're going to be doing.”
But it's funny that I would almost force people to try something, to try it. Come up with some kind of proof of concept, come up with something quick, whether that's done centrally or whether that's you empower the people to do it, and see what the results are. It's not going to be perfect. I mean, by definition, it's something quick. But measure whatever it is that you have built, and you can start anywhere, in any department, any function. Let people try it, and collect feedback from them on what happened, what worked and what didn't work, and then go to the next step.
So AI is very rapidly moving, so I would definitely do that. And then the second thing, definitely keep informed about what's going on in the AI world and what new things are coming out. So as a word of caution, a couple of years ago, there were many companies who went down the path of these large initiatives, built training their own LLMs in-house, all kinds of initiatives, which within the six months have just become commodified because all the large players like the Googles, the OpenAIs, the Anthropics, they just release those as features.
So, you don't have to make a gigantic investment, especially in something which you see that, in 12 months, that OpenAI is going to release it for free as part of the product. But make sure you get adoption so that you know, for your specific company and your specific use case, what works and what doesn't. You'll almost certainly find that there are certain unique use cases for your company where AI makes a lot of sense. And on the flip side, something extremely hyped up by the industry just doesn't work for your company. So try quickly and get feedback is my advice.
Gemma Versace:
And I absolutely love that advice. I think that doing something quickly is so simple, but also so compelling and so definitive. I love it. Do something quickly, and I think your other advice is also spot on in that don't try and replicate that of what other people are doing within their business. Find something that is going to be uniquely meaningful and uniquely moving the needle for your business, for your team, or for the industry that your business is in. I think that's such great advice. Do something quickly and really make sure that you're using AI to enhance your unique value proposition within your teams. That's fantastic advice.
Andy Sen:
I think in the age of AI, your data and your processes is what's valuable. That's something no one else has, and that's what you need to replicate. On the flip side, and I'm not saying anybody's actually thinking about that right now in 2025, you'd be a little crazy if you wanted to go ahead and build your LLM of your own. There are four or five global players who are literally spending hundreds of billions of dollars building their own LLMs. It makes no sense to really compete in that unless there's an incredibly compelling use case that you have. So focus on your strengths, focus on what makes you unique, and I think AI is just going to accelerate that trend enormously.
Gemma Versace:
Yeah, fabulous. Great answer. Lastly, so the X-Team Keep Moving Forward podcast is very much focused on understanding what does “keep moving forward” mean to our guests. So I'm going to ask you the same question here, Andy. What does keep moving forward mean to you right now, and especially in a time of so much AI-driven change?
Andy Sen:
I think keep moving forward to me means keep learning.
If I look back on my career, at every moment, the one constant has been that things have changed. The technologies have changed. The way we do business has changed. I'm talking about online commerce. The actual physical devices where we do our work has changed. Everything keeps changing, and AI is simply accelerating that rate. So you have to have that mindset of thinking the way that your business and your operations worked in the past is probably not going to be the optimum way in the future. So be open to new things coming in, have a process, whatever it is, of being able to evaluate new information and be able to act on them quickly, is to me the idea of keep moving forward. You want to see where you're going, make sure you don't step into a hole, but just keep going forward as quickly as you can.
Gemma Versace:
Fantastic. Great advice on everything that you've shared today. I have thoroughly enjoyed talking with you, Andy. Thank you for being so open and transparent about all of the wins and successes and also sharing some of the things that you guys are working on at AppDirect to keep moving forward and to keep ensuring that, from a leadership perspective, the empowerment and engagement being at the forefront of all things, making sure that the AI initiatives and innovation is really harnessed at AppDirect. Thank you so much for joining us today.
Andy Sen:
Thank you, Gemma. It was a pleasure to be here. I love talking about this, and yes, for everybody, let's keep moving forward.
Gemma Versace:
My conversation with Andy highlighted how powerful it is when culture encourages people to try new things and learn as they grow. His stories show how innovation grows when teams have ownership, guardrails that support them, and leaders who celebrate what they create. Andy's experience leading global teams also offered real insight into the importance of connection. Keeping cross-functional teammates in the same region, giving them clear responsibilities, and creating space for collaboration helps drive both speed and trust.
His view on AI was refreshingly practical. He shared why early chatbots fell short and why developers should see AI as a tool that expands what they can do. His message was simple and clear: Start small, try something quickly, learn from the results, and stay focused on what makes your company unique.
Join us next time for more conversations with technology leaders who help us to grow, lead, and innovate. You can find us on Apple Podcasts, Spotify, or YouTube Music. And if you enjoyed this episode, please share it with your network. Until next time.
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