Scale Like a CEO

From Founder to CEO: Scaling Teams & The Future of Early Career Talent | Mike Roberts

• Justin Reinert • Season 1 • Episode 48

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Stuck in founder mode and drowning in decisions? Justin sits down with Mike Roberts, founder of Creating Coding Careers, to trace the moment he stopped being the default problem-solver and started building a leadership engine. Mike shares how a bold re-org, strict guardrails, and an outside consultant turned constant firefighting into a cadence of rocks, quarterly priorities, and clear roles—freeing him to drive revenue and partnerships while leaders grew their own judgment.

We dig into the experience gap that stalls entry-level tech talent and why apprenticeships create a faster, safer bridge into real jobs. Mike breaks down a company-driven earn-and-learn model that pays people to master skills on the job for about a year and connects them directly to hiring pipelines. Along the way, he challenges the AI storyline that sidelines juniors. Most of the economy runs on small businesses still figuring out AI adoption, and pairing motivated early-career pros with modern tools can slash time-to-productivity. No juniors means no mids, and no mids means no seniors—talent ecosystems require constant planting.

The conversation also maps a practical playbook for promoting leaders: hire for growth mindset, reward extreme ownership, and anchor every decision in values—tenacious, resourceful, passionate, honest, responsible. If your calendar is clogged with validation requests and your team asks how you would do it, it’s time for a hard break. Learn how CCC banned direct escalations to the founder, empowered a true leadership layer, and built a culture where wins are celebrated and then leveraged for the next leap.

If you’re scaling a team, navigating AI headlines, or exploring apprenticeships to build your talent pipeline, this one’s for you. Subscribe, share with a fellow builder, and leave a review with the one guardrail you plan to install this quarter.

Mike:

It's really being able to say this person is at a phase where I need to allow them to make mistakes and I need to allow delegation to happen. And we have to put a lot of guardrails. Beginning of this year, we had to put a bunch of guardrails around me and say, okay, Mike is no longer allowed to do this. And everyone on the team is no longer allowed to directly go to Mike. And instead, they've got to go through this other individual. So starting to do that re-org and shifting the organization away from me sort of hand holding a lot of the team and feeling like I could train them up and I could have a bunch of direct reports to like it's not going to work. It's not going to scale. And we were hitting some of those growing pains where my time was just consumed, and the staff was really dependent on me to make them feel like they could make the right decision, but they wanted to be validated. They wanted to know that that's how Mike would do it, or that's what Mike thinks that we should do.

Speaker:

Welcome to Scale Like a CEO. In this episode, host Justin sits down with Mike Roberts, founder of Creating Coding Careers, a nonprofit transforming early career pathways in tech. They'll explore leadership lessons, strategies for scaling teams, and the evolving landscape of early career talent in an AI-driven future.

Justin:

Mike, thank you so much for joining me on Scale Like a CEO. Just to get us started, if you wouldn't mind, give us an intro to you and your business.

Mike:

Sure. My name is Mike Roberts. I'm the founder of Creating Coding Careers. We are a nonprofit organization. I founded about six years ago. And we are building the playbook for company-driven earn and learn pathways. What that means in regular speak is we do lots of work around registered apprenticeship programs and apprenticeship degrees. Fun stuff. We pay people to learn and in some cases get master's degrees.

Justin:

Well, that's incredible. I love that. And you tell me a little bit more about what problem you're solving and why it matters.

Mike:

Yeah, I was a software engineer by trade. I've been writing software for more than four decades. And when I left the job as a engineer and went to work at a coding boot camp, I found that for a lot of folks, it just wasn't enough time for them to get gain the new skill set that they needed. There's also this experience gap. Once they had a little bit of new knowledge, they still didn't have a lot of experience. And we were seeing that it would take them another six months or so working at a small startup before they would be appealing to a larger enterprise organization. I thought rather than having all the small startups having to groom this new batch of students, why don't we focus on solving the real problem, which is giving people enough experience where they are then interesting to larger organizations? And it's about a year of experience. And it turns out that that's pretty well aligned with apprenticeship when you look at what a typical apprenticeship experience looks like, about a year of working, learning on the job, working with a master uh craftsperson, and then having a quick pathway into an employer. There's an employer on the other end of every apprenticeship. Not only is it an immediate job, but there's alignment with a pipeline of organizations that are wanting to pull talent out of that, that type of program.

Justin:

Great. I love that. And I love programs that focus on getting people job ready and you know, very kind of intensive job readiness, uh, which is great. So let's talk about creating coding careers and you know, kind of starting that up and building it. What was the biggest shift that you had to make personally as you moved from kind of founder to really being the CEO and growing your team?

Mike:

There were really a couple shifts. The first shift was going from being an individual contributor. So I went first when I left the job as a principal software engineer. I first went to work at a coding boot camp and I was the chief academic officer. So I was largely responsible for classroom experience, for hiring new instructors, for the overall learning trajectory of the individual participants, the students. Um, but the school abruptly closed down after I'd been there for a couple of years. And I had to immediately decide did I want to take everything that we learned and start a new business and start my own program, or do I want to go back to being a principal software engineer? So I chose to start creating coding careers. At the time we started as a for-profit coding boot camp, similar to the program I came from. And so I immediately was in this solo entrepreneur experience that was new to me. I had done freelancing work before as a software engineer, but never run a business that required me to hire some additional staff and have a physical location, all of those things. Then I had to shift from that process of just starting everything, building everything, um, and iterating on what I had learned, but had to implement myself to having to then grow a team and step out of the role of operations and step into a role as a CEO and begin to build out more of a leadership team, more of a strategy on how we were gonna grow and expand into a market in the workforce development space that can be very, very challenging. There's lots of whether it's in fundraising, all of those things were brand new. And I needed to bring in the right people and have the right folks in seats to be able to scale the business.

Justin:

So looking back as you were building the team and kind of needing to let go of some things, what role was the hardest to let go of and what made it difficult to delegate?

Mike:

Well, again, we're six years in as a nonprofit. That's a that's a lifetime, right? And six years in the current administration feels like even longer, COVID and everything. So it feels like almost dog years, right? And for me, it's always been because I've been one of the more seasoned experts in this space the whole time. It's really being able to say this person is at a phase where I need to allow them to make mistakes and I need to allow delegation to happen. And we have to put a lot of guardrails. Beginning of this year, we had to put a bunch of guardrails around me and say, Okay, Mike is no longer allowed to do this, and everyone on the team is no longer allowed to directly go to Mike, and instead, they've got to go through this other individual. So starting to do that re-org and shifting the organization away from me sort of hand-holding a lot of the team and feeling like I could train them up and I could have a bunch of direct reports to like it's not gonna work, it's not gonna scale. And we were hitting some of those growing pains where my time was just consumed, and the staff was really dependent on me to make them feel like they could make the right decision, but they wanted to be validated, they wanted to know that that's how Mike would do it, or that's what Mike thinks that we should do. So it was like we had to make a very hard break, and we had to say, no more, no mass, it has to shift. And then we brought in a consultant to also help us with working on the business and started to zoom out instead of every day being consumed by the daily operations work. It was much more about okay, we need to set a broader strategy, we need to really think differently and go through not just a SWOT analysis, but really breaking things into rocks and then thinking about quarterly objectives, and then really taking some time to organize, which we just hadn't done because we were all just firefighting, trying to keep growing, and we just have not had the break to be able to maintain a certain size. We've just been scaling year over year constantly and seeing a constant increase in demand for early career talent. So yeah, it's been it's been interesting to to not have that break where we kind of plateaued and stayed at the same size for a significant amount of time. It's just been constant growing pains and learning.

Justin:

Yeah. I'm gonna go off topic. I want to go on a little offshoot on something you just said about the demand for early career talent. So if you if you are reading the headlines, there's a so many headlines about how early career talent isn't needed anymore because of AI. Like AI is replacing new college graduates and people with low experience. But it sounds like that's not the case in what you're seeing. So I'm just I'm curious kind of what what you're seeing and how that compares to what the headlines we see.

Mike:

Sure. Well, I think the headlines in many cases are focused on sort of following big name, big logo organizations, right? And it they frankly, they do have lots of folks. They may have overhired during COVID, and they may have overhired when it was less expensive to do RD and cash and all of those things. And so there's a natural you know, swinging of the pendulum back and reducing their staff and their size, and there's the uncertainty of AI and their wars, and there's all sorts of things that are causing organizations to go where it makes the most sense, which is to go smaller and to get rid of uh staff that you can shed if you can do that to lower your costs. And that's a typical tactic of large organizations. But most people forget that our economy is driven by small businesses. Vast majority of our economy is organizations that may have 50 or less individuals, and those organizations are not in a position where they're like all on top of AI and they figured out how to leverage it and incorporate it into their business. They are struggling, just like large enterprise, to figure out how do they adopt this technology, how do they use it to grow and scale. And it's across a bunch of industries, it's not just technology or or software engineering. It's like, how do we incorporate AI into agriculture, right? Because our competitors are doing it, or how do we incorporate it into advanced manufacturing? Because you know, we build things whether here or somewhere else, and we don't want to get beat by our competition. So we've got to you know be on top of whatever that our competition is doing, which is embracing technology and trying to figure out how to leverage you know AI. So I tend to think that the smart money is not listening to the noise and you hear the big headlines about thousands of people. I think today it was thousands of people laid off at I can't remember the name of the company. It's gonna date this episode, but it just hit that I wasn't saying 10 to 25,000 people were laid off at insert big name of a tech company. And I thought, okay, yeah, but you know, when you're at Walmart scale and you're like, you know, several million employees, laying off 25,000 is like not it's not the same as a 25-person company that has to like let go of a quarter of their staff, right? That makes a significant impact on their business. So I don't want to downplay like how challenging it is right now to to land a new job if you've been laid off, or the fact that lots of jobs are being shifted, you know, offshore, right? And so, but we see that it's very cyclical. We see cycles of jobs being offshored, and then about a decade later, you see them all coming back here in the United States. I just think that's part of the normal business cycle. Where I think there's opportunities for folks when they think about early career, is to think more about how much more efficient an early career person can be when augmented with AI, and how much faster you can ramp an early career professional than in previous years. It might take you so much longer to help them understand your business and help them be productive and help them get to billable hours if that's a way that you measure their productivity. And I think the smart money is on companies are now's the time to double down to grow your own talent and to figure out how you can use AI to get people up to speed and more profitable for your business earlier on. Because here's the thing everybody talks about getting rid of the junior engineers because now you know you don't need a junior engineer. That's sort of true, except for the fact that you don't get middle-level engineers if you don't hire juniors, and you don't get senior engineers if you don't hire middle levels or juniors at some point. So, like, if you think about it, it's like the rainforest, right? You have to plant new trees. And if you don't plant new trees because you think, oh, there's no need for them, we're kind of missing the big picture. So I know it's a bit of a ramble, but my thoughts on that are much more bullish on early career than I think the the current narrative, which is oh, you don't companies don't need them.

Justin:

Yeah. Well, I appreciate that because I I also I definitely agree with the perspective of we have to nurture early talent to continue a pipeline of people that will run our businesses. Because if if we're saying that only experienced people are valuable right now, then that's gonna run out eventually. We've got to continue to grow and and nurture that talent. I shifting back to kind of leadership and scaling, I'd love to hear as you have been growing, what are some of the qualities that you look for when you are promoting leaders in your business?

Mike:

Promoting is easy because for me, promoting is really about handling more on their own, making good judgment, good decisions. And I always want to promote as fast as I can internally and give people as much as they're capable of doing. I'm not a gatekeeper, and I love when I hire people, I love telling them like I want people that can take ownership of tasks. And once you're competent and you understand how the business goes, I want to like let you loose and let you become an entrepreneur and help us grow the organization. I love that mindset and that mentality. So I always want to feed that as long as someone has like a growth mindset. I think that's like super helpful for me to identify. And once I can see that, I also tend to be a little bit more direct, kind of more old school, and less of that like nurture instead. Um sort of like this is gonna be tough love, but it's because I want to bring people in that I know are a players and I know we can get the best out of them if I high hold them to high expectations, and then we celebrate wins, but we don't spend a lot of time patting ourselves on our back. We got there's more work to be done, and so I tend to hire for those qualities to like want to move people up within the organization that can demonstrate that they can take ownership, they can take extreme ownership, right? We want to use that, and then they have that entrepreneur mentality. I think that is a huge differentiator. If they don't have that, then my job is to coach that. And that's an expectation I have of a lot of the organizations that I've been inside of and led. That you want to have, you know, it's one of those valuable habits of employees, is that they think about how they contribute to the organization and they're not just in an individual contributor, even a leadership mentality. I think really have to think about how what do they mean to the organization? And then how do they build habits that help to reinforce they are valuable to the organization?

Justin:

Yeah, I and I love that you started with growth mindset. I think that that is something that, you know, no matter the role, is something that I'm always screening for. Um, because it's so valuable to have that in your people and in your organization. But so you know, as you grew creating coding careers, um, you know, what were some signs that you needed to shift your team structure?

Mike:

Man, it was just increasingly more challenging for me to remain calm and um in this it was just so and it felt so chaotic to have so many things pointed in my direction and have so much ultimately so much responsibility falling on my shoulders. I don't even know how I sustained it for the length of time that I did for like the first five and a half years or so. There's only been a good six months where I was like, okay, we're done, time out, we need to re-org. And it we we grew. You have to crawl, then you walk, then you run. And you know, we grew to a point where it was just not sustainable. We were just we were on a hamster wheel, and I had to get off in order for us to unlock sales so I could get back to being the chief salesperson for the organization, generating enough revenue, and then we had to sort of make sure that everybody else was very clear on what their role was, what their expectations were. A lot of the employees that we've had have been with us from the very beginning, and so they came in as more junior in their role and they've grown into leadership roles, but it's hard when you start with a small team and everyone is early, right? Everyone requires a lot of coaching. And while they might have some deep expertise in particular areas, it wasn't in leadership, and so I had to grow a whole crop of leaders within the organization and then help them to in and enable them to be leaders by giving, delegating more responsibility to them. Yeah, it was a very challenging journey. But so proud that we made the decisions that we did to re-org, to bring in an organizational consultant to work with us on an ongoing basis. Without that, I don't think I would have already been burnt out and everything would have just fallen apart. So it was a critical step for us to acknowledge that okay, this is not gonna work anymore, and then take the steps that we needed to re-org and get help. A lot of people don't want to do that, they don't want to bring somebody in and have them point out this isn't working, you need to fix X, Y, and Z. Then 100% to trying new things and testing things out as long as it makes sense.

Justin:

That's great. And so, how do you define the leadership culture that you want to build for the future?

Mike:

I mean, we have core tenants within our organization, and for me, everybody has to embody those core values. That to me is the that's the foundation, right? The core values that know and live the core values. If they can't, then there's we have no no place. And ours aren't fancy, they're just what we came up with as a leadership team. And things our values are tenacious, resourceful, passionate, honest, responsible. If they're not down with those values, they're not gonna be as successful in this organization. Like we've decided as a team, like we have to rely on people that can manifest those core values.

Justin:

Yeah. Well, it's great that you have that values orientation and you you know hire around it and have discussions around it. Successful organizations that I've seen are you know, one of the things that they do really well is they're very clear about those values and how they um how they design talent around that. Well, Mike, I really appreciate the conversation today and thank you so much for the time. If folks want to get in touch with you, what's the best way to do so?

Mike:

Sure. So the best way to reach me would be via our website. So that's cccareers.org. And I'm also on LinkedIn. And so if you look up Mike Roberts, you'll find me. There's other Mike Roberts', but I'm I think I'm the most popular at this point. But yeah, those would be the two two places, and we're always interested in having conversations with any companies that are interested in learning more about apprenticeships, learning about apprenticeship degrees. Happy to have that conversation all day, every day.

Justin:

So well, I love that you're coming up as the top Mike Roberts on LinkedIn. Oh so well, thank you so much, Mike.

Mike:

Yeah, absolutely. Thanks, Jason.