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Foreign. Welcome to Coruscant Technologies, home of the Digital Executive Podcast. Do you work in emerging tech? Working on something innovative? Maybe an entrepreneur? Apply to be a guest at www.corazon.com brand welcome to the Digital Executive. Today's guest is Nicholas Jenest. Nicholas Jenest is the founder and initial CEO of Codebox Technology. Nicholas is a 2 times CEO and 5 times CTO multi exit technology operations and digital products executive who has successfully founded, built and operated leading businesses. Some of them generate over $1 billion in annual revenue. Launched goodwillfinds.com in 2022 to transition goodwill into the digital age. Awarded the best AI chatbot solution of 2025 and has fought food waste at full harvest and founded Codebox Technology Academy providing accelerated AI first technology education and employment to individuals from all walks of life. Previously led technology during the hypergrowth phase of venti. Priby, now VP, was first CTO of the RealReal and transformed the commerce practice at ModCloth and later at Walmart after acquisition. Well, good afternoon Nicholas. Welcome to the show.
B
Well, thanks for having me Brian.
A
Absolutely my friend. I appreciate it. You're in St. Petersburg, Florida. Currently I am in Kansas City, so only an hour apart but luckily the weather's a little bit in your favor typically. I know it's getting chilly there too so. But Nicholas, let's jump into your first question. You founded Scale that exited multiple businesses, sometimes reaching 1.1 billion-plus in annual revenue and then turned your focus to founding Codebox to train diverse talent. What was the moment when you said I need to move from building businesses to building people? How does your experience as the CTO or CEO shape the way you design Codebox?
B
Well, as you said, like I've been the CTO and technology leader on a lot of companies, like a lot of startups. Like it started back in France at the inventor of flash sales VP. Then I got poached by the RealReal to be their first CTO in 2013, moved on to Maclau to rescue the brand. We got acquired by Walmart and there's a common theme for all the teams I was building and the experiences I was living as a technologist throughout the build out of those companies. And it was you can achieve great things for these companies if you have the right people behind the technology. In other words, it's not about the stack, it's not about the choices of tech being made. Is it custom built, tailor made? Is it best of breed integration of systems? What really matters is is the team behind it executing on the plan that has been chosen Are they business first, are they results oriented? Are they in agreement with you that it is a fail fast environment, it's all in execution and not losing sight of what truly matters for the business. And when I understood that, to me it felt like a discovery. And I realized that the places I struggled in my career in my companies was when the wrong people were in charge or accountable for things that really mattered. So what triggered the foundation of Codebox in 2018 was we need more business first people in technology so that we can reach our goals and we can manipulate and control technology so we can really put it at the service of the business and make it as an enabler instead of having it technology centric all the time. So that's really what triggered the need for Codebox to exist, is find the right people, business first, with grit, with experience, who care for the outcome and the customer and the users and the stakeholders of the company and make them do great things by teaching them hard skills of tech.
A
It's amazing. Thank you. And I took, took away a lot here, which is great. You've had lots of experience in startups as a technologist or cto and what you came out of this, you learned from your experience. Basically having the wrong people in the wrong positions can really impact the business, especially startups. But your company can do great things if you have the right people behind the technology, that they're business verse, results oriented, they can execute on things. So I really appreciate you sharing your insights with us and Nicholas. Codebox emphasizes that smart is everywhere and that background or formal credentials shouldn't limit access to technology careers. How do you identify and coach people who may not have traditional tech credentials? And what traits do you see that predict long term success in those students?
B
Well, that emphasis on smart is everywhere has evolved into new kind of smart with the emergence of generative AI three years ago. So like November 30, 2023 will always be remembered as a turning point in the technology field because it kicked off revolution where everybody got smarter, Everybody, everybody got equally knowledgeable and everybody got equally capable. So it literally leveled the field between 20 year old senior coders and software engineers and newly arriving AI native technologists who actually can focus their time on the requirements and the operationalization of the AI output. So since coding is no longer a barrier to entry to software development, what remains is the people behind AI. And the new kind of smart means we're doing great with waiters, tired nurses, Uber drivers who remember everything, Starbucks baristas who are like super customer oriented and outcome Oriented and want things to be just right. These kind of people, if given the right AI native skills and managed to cut through the noise of all the tools that are available and they're not all good, they will be augmented in a way where they can be super impactful within a business because they the grit and the business bias and the propensity to deliver that they show naturally as individuals in their personality and in the way they are, and through their human skills, it can be turned into very valuable assets for a company when they're augmented and tied to artificial intelligence.
A
Thank you. And I would certainly say that would resonate with me obviously, but with a lot of people, you know that with the generative AI explosion in the last three years, there is really no longer a barrier to entry when it comes to coding. And you're right, over my career in technology, we've hired a lot of business people with no tech background into the tech space. And it brought a different set of thinking and there were different ways that we looked at outcomes and it's been a positive thing. So I appreciate you sharing your insights as well. And Nicholas, under your leadership, Codebox developed an award winning chatbot solution GEM Chatbot for Goodwill Finds named the Chatbot Solution of the year in 2025. What makes an AI or chatbot solution business first in your view? And how did you build a bot that not only works but drives measurable results rather than just being a novelty?
B
Well, we were really surprised to be awarded best chatbot with what we had delivered at Goodwill Finds. It came out as a surprise in such way that we even felt the need to like document how we did it. And we deconstructed and we broke down what went right in delivering that solution to the world so that we can really understand what set us apart. And it really is four things that we really landed and mastered that led us to win that award. The first was we briefed the conversational agent perfectly on purpose. So we were able, through a very extensive documented prompt, very elaborated what this agent was meant to be, what the guardrails were, what the purpose was, in what order things were meant to be done, what knowledge was supposed to be top of mind as it was conducting conversations with customers. And that brief is really what we call the, like the consciousness behind the capabilities of AI. So we collaborated with true customer service people and we broke down every single conversation that they had recorded and done in the past to understand how the ideal conversational agent called Jim would behave. That was the first pillar. The second pillar was what Knowledge, does it need to have to be successful? So general knowledge knowledge, like frequently asked questions, statement of processes, past anecdotes and past experiences, like a knowledge base of things it needs to do and things that it shouldn't be doing and it absolutely cannot do. So that's the core knowledge that need to be fed systematically. When a conversation is spun up, the third pillar was around giving it arms and legs. So it's one thing to know things, it's another to be relevant. And then that third pillar serves that purpose. So arms in the sense where you can send it everywhere, like legs in every corner of your databases of your. You can program, provide it with contextual information, you can feed it with profile information once you know who the customer you're talking to is and it's authenticated, and then you give it things to do and things it can do. So the more arms and legs you give to a conversational agent, the more possibilities it has to satisfy the customers and close on the, the case itself. So that's that that was key. It's like, is it a good case to refund? Is it a good case to make an escalation? Is it a, is it a case where I'm going to recommend an alternative item for a broken one that was delivered? So in order to achieve all of this, you need to give it access to inventory, you need to give it access to the profile information of the customer, you need to give it access to the last 10 orders, the tracking information of the parcels that were sent out on its behalf. So all of this needs to happen. And that's the third pillar that we nailed. Like contextual information at the right time through retrieval, augmented generation and the like. Very thorough, solid functions that really make a difference for the customer. And the last, the lengthy answer, I apologize, but like, the last fourth pillar was constantly monitoring the conversations. Like, like you would supervise an employee in the early days of their jobs to know and understand how much they can be left alone. It's the same with an agent. You plug AI into monitoring the conversations that happen, the outcomes that are obtained. And you adjust constantly, like almost daily in the early days of the release to make sure that you course correct the behavior. And the next thing you know, a few months in, you don't even, you don't even. You do no interventions anymore. And it's completely autonomous and it, it satisfies more than 80% of the people. There is no escalation required, and customer service ends up winning its own prize. So we were pretty proud of, of.
A
That approach, that's amazing. I really get excited about the technology that is getting better each year and I think that's amazing. And you broke out the pillars. I know you were surprised that you got the award, but it made a lot of sense. And those four pillars, just real quick is you really got focused, you elaborated on what the conversational agent should do, the end goals, guardrails, etc. In that, that whole conversation, that knowledge that the agent needs to have to be successful, that that was important. Giving it arms and legs, as you said, it's important that the agent is relevant. More possibilities, giving it more again access those arms and legs to do more things and then constantly monitoring and adjusting, improving the call and the outcome. I think that's so, so important and we need to focus on that for sure. And Nicholas, the last question of the day. Looking ahead, how do you see the intersection of tech education, AI adoption and workforce development evolving by 2030? What role do you hope Codebox will play in that future? And what challenge do you believe deserves more attention right now?
B
Well, if you look at what Codebox was created for in 2018 and like the first 300 graduates we've had, they were really taught the like 60% coding and it was about making sense of the latest software as a service capabilities and making sense of the cloud. And it was really about that. But over the past 18 months, I would say it our purpose really evolved into no longer seeing coding as a barrier to entry, like I was saying, but making sense of the immense power that AI brings to the table and making sense of like what are the best tools that are available to you today to to do a good software development job and to reach, to reach time to market faster. And how do you spend more time reaching what I call user experience fit on the journey to product market fit? You have this moment where what you propose in terms of software reaches and resonates with its users and AI can definitely help you get there faster and iterate more frequently. And there's this whole trend around vibe coding that's gaining steam right now. We're at a very critical time of that trend where it's either going to deliver on its promises or it's either going to fall on its face. And Codebox's role in this is to make sure that CEOs marketing leads digital product owners, stakeholders of companies, they can actually express requirements in natural language. And we managed to remove those interpretation layers that used to exist, like user stories and like sets of requirements and breakdowns into code, like those Interpretations are no longer required. And AI can do a good job producing software just straight out of requirements. So teaching people what to ask for correctly in their prompts and help them make sense of the output, make it secure, scalable, compliant and pleasurable for the users so that adoption can happen. Those are the true focus. That's the true focus where our profession is shifting to. And I think those who will be successful will understand that migration and will focus on these things instead of of of coding.
A
That's great and you had the right mindset in my opinion. You are looking forward that visionary type of leader. But just to kind of COVID a couple of things that you talked about here. I know code box has evolved and you said the last 18 months obviously is you look at things a lot differently teaching students what is really making sense as far as the platforms today that's going to allow you to build the best platform, the best product and get it to market faster. But AI is certainly getting good enough to do the business requirements interpretation, leaving more of that critical thinking and visionary type strategies for people so they can focus on really building a better outcome and a better product. So I appreciate your insights and what you're doing with Codebox. And Nicholas, it was such a pleasure having you on today and I look forward to speaking to you real soon.
B
Thank you Brian. I really enjoyed my time with you. I hope there's a next time.
A
Bye for now.
The Digital Executive — Episode 1146: "Building People, Not Just Tech: Nicolas Genest on AI, Talent, and the Future of Work"
Host: Brian (Coruzant Technologies)
Guest: Nicolas Genest, Founder & CEO of Codebox Technology
Date: November 16, 2025
Duration: ~18 minutes
In this rich and insightful episode, host Brian interviews Nicolas Genest, a seasoned technology leader and founder of Codebox Technology. The conversation explores Genest’s career arc from building billion-dollar tech businesses to building diverse human talent for the future of AI-native work. Genest shares how Codebox focuses on unlocking opportunities for people with unconventional backgrounds, what makes business-first AI solutions succeed, and his vision for the intersection of AI, tech education, and workforce development by 2030.
[02:09 – 04:37]
[05:30 – 07:39]
[08:33 – 13:21]
[14:26 – 17:07]
"It's not about the stack... What really matters is the team behind it executing."
— Nicolas Genest [02:54]
"What triggered the foundation of Codebox... we need more business first people in technology so that we can reach our goals and... put it at the service of the business."
— Nicolas Genest [03:28]
"November 30, 2023 will always be remembered as a turning point... everybody got smarter, everybody got equally capable."
— Nicolas Genest [05:46]
"Waiters, tired nurses, Uber drivers... if given the right AI native skills... can be super impactful within a business."
— Nicolas Genest [06:32]
"We briefed the conversational agent perfectly on purpose... That brief is really what we call the consciousness behind the capabilities of AI."
— Nicolas Genest [09:18]
"The more arms and legs you give to a conversational agent, the more possibilities it has to satisfy the customers."
— Nicolas Genest [11:00]
"Teaching people what to ask for correctly in their prompts and help them make sense of the output... That's the true focus where our profession is shifting to."
— Nicolas Genest [16:35]
This episode is essential for anyone interested in the future of work, the real impact of AI and automation on talent development, and pragmatic insights on building both technology and teams in a rapidly evolving digital landscape.