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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.corazant.com brand welcome to the Digital Executive. Today's guest is Dan Benvenisti. Dan Ben Benisti is the founder and CEO of Skillways. He's a serial entrepreneur with over 150 million in successful exits. 25 years of executive leadership experience from startup co founder Foglike Software acquired by QSFT to a global executive, NASDAQ and eft.com Skillways evolved from Startup Genius Inc. In 2015 to help Gen Z innovate. In 2021, Ben Benisti founded alumnibridge.com, which accelerates the future of work with its AI powered, individually curated, real time, learn and earn platform for entry level skills based talent development at scale sponsored by NPOs and employers. Now the enterprise can develop and hire the actual skills they need in early talent from their own branded virtual talent pool farm teams just like the Yankees. Well, good afternoon Dan. Welcome to the show. Thank you. I appreciate you jumping on my friend. I know you're hailing out of Scottsdale, traversing the time zone to hit me here in Kansas City, so I appreciate that. And Dan, if you don't mind, let's jump right into your first question here. You have 25 plus years in leadership, multiple successful exits, and now you're focused on early career talent through Skillways and Alumni Bridge. What prompted the shift from from more traditional tech businesses into the work of Learn and Earn and bridging the skills gap?
B
Yeah, great question. During the corporate grind, so to speak, in my younger years I was flying around the world and found myself many times looking down, especially in the United States, saying there's just not a lot of the actual people in the US participating in the innovation economy and doing a lot of the east coast, west coast stuff. You got California and New York who have always been the hallmarks of the last 50 years of finance and innovation. And pretty much around 2010 to around 2013 and 14, it really started to sink into me that 48 states, everybody in the middle aren't participating in the innovation economy. And so I started the company under the original name of Startup Genius Inc to teach entrepreneurship through SAS application and sold it to 14 states, high schools, colleges and universities starting in the middle of the country in Pittsburgh, Kansas, so a little south of where you are and grew into a little scenario where we had a customer come to us in 2018 and 19 University of Nebraska. And they came, came to us and said, we have a corporate partner, Union Pacific Railroad, right here in Omaha, who would like to have the kids solve a problem that they have instead of the kids coming up with their own ideas and solutions and entrepreneurship stuff and they'll put up a thousand dollar prize award. So we did. We said, great. We have this really cool skill data. We can show how the kids are working hard, which one. We can show the quality of their work product through the iteration process of how they're solving problems and they're communicating with each other. And then we can also present a score on how well they present and show their work. And we distilled down also a observation of nine key soft skills. So we put a thousand dollar prize award at it and the kids went to town and they started coming up with ways to solve that problem problem for Union Pacific Railroad. And by the way, the problem was really interesting. It's called positive train control, which is congressional speak for trains fall off the track and hit cars, trucks and people. So the kids went at it and they presented their solution. At the time, the CIO and a couple of the other team on the at Union Pacific Railroad said, this is really cool, we'd like to buy a license so we can do this ourselves. So we ended up putting together a commercial package and licensing the platform to Union Pacific Railroad so that they could start recruiting. And so we, we did that. And then right during COVID or just before COVID they had a couple of big management changes and it was, we were doing virtual internships and innovation challenges and skill and scoring kids through the process. It was kind of like selling umbrellas in a hurricane, right? It was like, hey, people need them. Everyone's buying virtual internships and innovation challenges. And we're doing little virtual apprenticeships and we're skilling and scoring. And we did it in about four or five other states. And it was kind of like, you know, it does feel like that umbrella in a hurricane. You need it, it works a little bit, but it's truly not effective the way that it could or should be. So I started talking with a couple of investment bankers and looking at acquiring a solution that would be a learning side of the platform. And much like you have in a big corporate enterprise where you can upskill based on what your job, next job might be and how to continue to migrate that. So I went on a hunt and acquired a company called Tiller from Canada doing a full enterprise learning management system. And that brought us to now Skillways, where We are offering a comprehensive learn and earn platform for both employers and potentially even to sell a subscription in place of those that don't want to go to college. They can buy a Amazon prime style pass to pick up the skills and credentials they need for a guaranteed outcome of career readiness for employers on the platform. So it was a few minutes longer to tell that part of the story, but that's how I got here.
A
That's awesome. Love those backstories. And I deliberately try to frame questions at the beginning around that so we can get that foundational backstory, which is awesome. And again, like many people, you were a busy executive in your past life and you said people just weren't participating in this innovation economy and you made a shift into this space and one thing led to another, obviously helping in the process, helping the world learn and earn while bridging that skills gap. But I just again love the different iterations of the business. Even buying a business, another company, and having a big company interested in your platform and just goes on and on and it's amazing. And at the end of the day you are making the world a better place. So I appreciate that. And dan, with over 150 million in exits and a quarter century of leadership experience, you've seen startups scale, exit and transition. What's one lesson from your big first exit that you wish you'd known earlier and are applying it now with Skillways or Alumni Bridge?
B
I love that one. It's kind of funny having been an angel investor, still am in a number of companies and was a limited partner in a couple of venture firms as well. The mantra heard especially through California, New York and London is fail fast. Which is money speak for put the money and get it to work. And if it's not working, punt and move on. Right, so you see a lot of startups get funded and then they also fail quickly because they truly haven't got to their market yet or the market wasn't ripe yet in most cases. So what I chose differently in this one was to take my time. I literally developed that backstory through much deeper process. I've not taken any true institutional money and friends and family and myself throughout the entire process. And so the fail fast piece really doesn't apply to the entrepreneurial mindset of no, you're solving a mission and keep working the problem until you get to the point to where it's now ripe and ready to go to market. So it wasn't a fail fast process for me. It was a succeed slowly or process so completely different lesson that I learned from, from the lessons I learned earlier, I needed to apply differently through this process. And we're just now in the position to where we're going to go, raise a significant amount of investment because I think the skills crisis and job turnover situation that AI is placing on people and on companies and the need for the next generation, generation Z and generation A to truly find their way, which some cases just degrees just don't do it. They don't get them into the workforce. They're not as prepared as they need to be. So I think there's a critical moment for us to really come to market and have the impact that we can have across a much broader population than we have in the past.
A
Thank you. Really appreciate that. And you're right. Talk to a lot of entrepreneurs here on the podcast. A lot of people say fail fast, right? And if it's not working, punt and move on. But I like your transition, what you learned from previous exits and apply it to your current endeavors. And it wasn't really to fail fast, but really to succeed slowly and do this the right way. And I can tell you right now, your platform is much needed across the world, this planet that we need, especially with AI. So I appreciate what you're doing. And Dan, with Skillways, you talk about providing guaranteed career readiness through AI powered virtual internships and and curated learning. What does guaranteed readiness actually mean in practice? And how do you operationalize it so employers trust it and learners benefit from it?
B
Yeah, great question. I love that. That's right down the middle for me. So what we've done is we'll take an employer and we'll say, give us your job spec. We'll distill the skills required for the job, not the degrees required. And with that we will then curate a program of learning curriculum. And that is sourced just like you might be if you're pulling it from universities, colleges and online learning, from LinkedIn learning to Coursera. So we're agnostic from where the learning comes from. So that's where we become the Amazon prime of learning. Right? We don't make the curriculum, but we make it better because we apply it directly on an individual personalized learning basis for each person, each participant, each student. So we'll curate the learning curriculum they need to acquire the knowledge of skills for that job. Then we will then apply a earning component to it. And that is the innovation challenge, the virtual internship and the virtual apprenticeship. And within that context, our artificial intelligence will observe, recognize, measure and score the skills required through that working process. So therefore we can take our learning verification of the knowledge that was acquired and we can show how it is, how it can be applied in a work setting and then the degree of proficiency of skill application. So think of the watch on your wrist that might count your steps, measure your heart rate. We observe the skills and do the same thing. Much like a prism will capture the light and break it apart into its respective color spectrums. We do the same with their work effort. So with the skills that we pull together, we feel pretty confident in our AI that we can guarantee on behalf of an employer their career readiness. We can verify they learned a skill and then we can verify if it can be applied and has been applied to what proficiency it provides the students, particularly the younger generation, the ability to proceed and progress their skill development and learning and application in a left foot, right foot progressive scenario. Unlike just getting an academic degree, popping out of college and then saying ta da, are you ready? Well, we don't know what for and so we actually do that preparation for them. So we're pretty confident about our AI and we're excited to work with some pretty significant large employers in the US to where we customize and tweak our AI for their needs.
A
That's amazing. I love that. And I like how you can go to an employer and say, hey, what is the job spec for these for XYZ or whatever that job is. And then you actually curate that curriculum for that particular program. And as you mentioned, you don't make the curriculum but you make it better, which I thought was interesting. And then of course you apply a learning, an earning component to this program as well, which is cool, but absolutely love your explanation and breakdown of this. I love what you're doing with the platform and I can't wait to dive in a little bit more. So my last question for you, Dan. Many traditional models still treat credentials, degrees and tenure as proxies for capability. Your work suggests a shift towards demonstrable skills, real world work and employer curated talent. How do you see the future of higher education and credentials evolving in that context?
B
Yeah, that's a phenomenal question. It's one I think that has been on the front mind of families who are getting ready to pay for college today that in the fear of will AI agent of AI take out the educational learning scenario from its traditional roots. So I think there is a fundamental shift in place across the board. We have many employers, we've had governments, local, state and part of federal governments say look, we don't need a degree for this if you have some coursework or any prior experience, then please apply just because it's so difficult. I think that many in most employers over the last 10, 15 years, when they put out a job spec, it's typically a wish list versus the actual hiring spec. And in that scenario for large employers it's kind of like, look, we can use this to pull in the volume and weed out and try to hope and find the best in that process on a competitive basis. And it's been largely successful to do that up until more recently in the last two years when you have everybody has access to an agentic AI chatbot and they say, great, take that job spec, write my resume so that it meets that need of that job spec. They send that in, they get hired. And then you see like we have last year and this year, especially in the college graduate high school scenario, they're getting fired 60, 70% of the time inside of 90 days. It's just a false positive, it's garbage in, garbage out from AI bot versus AI bot. And so we're seeing that now the bigger need for a true understanding of demonstrable skills that can be verified by somebody.
A
Right?
B
And that's super important. And just a resume doesn't do it, a static resume, a self authored resume doesn't do it. And so we will be actually acting as a broker in that context. We will verify the resume, we will write and author the resume that goes to the employer. And it is our verified data that the employer can rely upon. And at the same point in time, so can that student, so can that young person or a re entry mom or somebody's doing a career change because they got laid off because of AI and they need to reskill. So we become the broker of record of that data. So we back it up and we verify it. You do the learning and the earning on our side, we'll back you up.
A
That's awesome. And I'd like, it's just quick takeaway. You stated you'd be a broker in this process, right? Validating the resume, the experience, the learn and earn part of it, which we talked several times about in this conversation. But I agree with you. The traditional education model is ready to be flipped up on its head. The bubble's going to burst. It's been headed that direction I think for a decade. And now with AI, it's just things are shifting. At the end of the day, both employers and graduates are ended up being disappointed. Right. So I really appreciate your insights, everything that you impact today. And I just can't wait to get this published. So, Dan, it was such a pleasure having you on today, and I look forward to speaking with you real soon.
B
I appreciate it. Thank you for taking the time to hear the story and to do what you do. I appreciate it greatly.
A
Bye for now.
Redefining Career Readiness: Dan Benveniste on AI, Skills, and the Future of Work
Guest: Dan Benveniste (Founder & CEO, Skillways; alumnibridge.com)
Host: [Coruzant Technologies]
Date: October 26, 2025
Duration: ~17 minutes
This episode centers on redefining career readiness in the age of AI and rapidly changing workforce needs. Dan Benveniste, a serial entrepreneur and founder of Skillways and Alumni Bridge, shares how his mission shifted from traditional tech ventures to tackling the skills gap through AI-powered, real-world learning experiences. The discussion covers the evolution of “learn and earn” platforms, breaking away from degree-centric hiring, and the crucial need for practical, demonstrable skills to meet the demands of employers and Generation Z.
Through his companies Skillways and Alumni Bridge, Dan Benveniste is challenging the tradition of degree-first hiring by delivering AI-powered platforms that connect real-world skills with employer needs. He predicts—and is actively building for—a world where validated, demonstrable skills matter more than diplomas or resumes for job readiness. This episode offers a vision for the post-AI workforce, urging employers and jobseekers alike to rethink how talent is discovered and developed.