Jessica Hinkle: SVP Strada Education – Investing in the Future of Education & Work

“Jobs today won’t look like the jobs tomorrow. We’re realizing that continuous upskilling is just going to be required.”
– Jessica Hinkle
Gone are the days when you could simply get a four-year degree, settle into a job, and coast. Because the pace of change has accelerated so dramatically, the traditional roles of today, are shifting quickly. On today’s episode of the On Work and Revolution Podcast, our guest Jessica Hinkle, underscores the importance of continuous learning and adaptation in today’s dynamic job market.

Jessica Hinkle is the SVP of Strategic Investments at Strada Education. Strada is an impact-driven education organization with a mission to strengthen the connection between education and employment. Jessica emphasizes the need for individuals to embrace multiple detours along their career journey, constantly connecting what they know and how they work. Tune in to learn more about the future of work and the latest developments in the world of EdTech investments.

Debbie & Jessica dig into:

✓ The changing nature of careers and the need to continuously upskill

The ever-increasing need to bridge the gap between education and careers

How strategic partnerships and founder-led mergers are becoming increasingly attractive to organizations seeking to simplify their tech adoption and integration processes.

The struggle in the current markets to raise capital and which investor pet peeve founders should avoid

About our guest, Jessica Hinkle:

As SVP Strategic Investments, Jessica evaluates potential mission-aligned investments and oversees Strada’s portfolio of mission-aligned investments and funds.  Previously she led Product Strategy and Innovation, working with Strada Collaborative organizations to identify and create new products. Prior to Strada, she held a variety of roles at Laureate Education, including as chief product officer for Walden University and co-founder of an innovation group that incubated new business models to address the needs of working adult learners. 

Jessica started her career in investment banking at Morgan Stanley and also spent time building the yoga teacher training business at Yogaworks. She holds a BA from Brown University and an MBA from Harvard Business School.

Helpful Links:

Follow Jessica on LinkedIn

Open for Full Episode Transcript

Open for Full Episode Transcript

Debbie Goodman  00:00

Welcome to On Work and Revolution, where we talk about what’s shaking up in the world of edtech. I’m your host, Debbie Goodman, and I’m the CEO of Jack Hammer Global, which is a global group of executive search and leadership coaching companies. I also act as an advisor to venture backed edtech companies. And my main mission with all of the work that I do is to help companies and leaders to create amazing workplaces where people and ideas can flourish and thrive. Which is why I’m really happy today to be sharing the platform with my guest, Jessica Hinkle, who is SVP of strategic investments at Strada education. For those of you who don’t know, Strada is an impact driven education organization, the overall mission of which is to strengthen the connection between education and employment, education, jobs, and workplaces. So Jessica’s got a really great role at Strada, it’s her and her team’s job to evaluate new potential investments as well as to manage Strada’s existing portfolio of direct investments and then they’ve got some early stage funds. Prior to Strada, she was with Silver Strand strategy and innovation. And prior to that, she had a very impressive long tenure at Laureate International Universities. She’s been Chief Product Officer, she’s led product teams, innovation teams, investment teams, and she’s seen the ins and outs of every aspect of higher education. And today, we’re going to be talking to Jessica about the future of work and how the connection between education and work, or jobs, needs to change. Just a tiny little issue, right? Welcome, Jessica.


Jessica Hinkle  01:50

Thank you, Debbie. It’s so great to be here. 


Debbie Goodman  01:52

Okay, so I think first of all, we need to help listeners to understand a little bit more about Strada as a whole and how it plays a role in this connection between education and employment. So firstly, Strada Education Foundation is an NPO, which does several things to advance and strengthen this connection. Just explain a bit more about the core focus areas?


Jessica Hinkle  02:16

Yes, of course. So we’re a new kind of social impact organization supporting policies, programs, and organizations that are focused on strengthening connections between post secondary education and training and employment. And particularly for those that have faced the greatest challenges to securing economic opportunity through post secondary education and training. We use five levers to drive our impact. Those levers include grant making, policy and advocacy, research, our wholly owned nonprofit affiliates, and, of course, strategic investments, which is the practice that I lead.


Debbie Goodman  02:57

Okay, well, that was a really neat summary. Thank you for that. It’s not entirely straightforward. And it’s great to get that in a very consolidated version. Okay, so let’s dig into your area of strategic investments. You look to invest in companies that can further this mission of Strada. And so if you can sort of segment those core areas, what would those be?


Jessica Hinkle  03:22

So we look at our work in terms of five pillars. The five pillars that we believe are really going to help us advance to our North Star. Our work based learning, so connecting what you’re learning to career, quality coaching, to map a career path through education and navigate challenges along the way. Affordability, expanding finance, financing options and financial aid and expanding alternative education pathways, employer alignment, and finally, clear outcomes, which is really about breaking down the barriers of our data systems to help students understand employment outcomes so that they can make informed decisions when they’re pursuing post secondary education and training.


Debbie Goodman  04:10

Okay, that’s quite a vast array of the types of organizations that you guys invest in, but also quite focused, which is great to hear. I mean, there are many venture funds out there. There are many early stage investors and they also have kind of like a bit of an all-over-the-show sort of strategy regarding investing. But it sounds like with Strada, it’s very much more focused on that core connection between the learning that one gets in order to drive employment, and we definitely see that there is a big disconnect. I mean, I’ve got kids in high school right now. We’re about to start the arduous process of looking at higher ed and college, and it feels quite terrifying to us, well to me, maybe they’re ok about it. But it’s terrifying to me in all of those aspects like how do I know what they’re going to be studying, is going to actually equip them for the workplace of the future, which is just changing so rapidly. The cost of education, which even to privileged households is still astronomical. So how does anybody who’s, you know, who doesn’t have the means actually afford an education? And then just the information that, that anybody who wants to equip themselves, be they at any stage of the learning, because I imagine there’re a lot of adult learners as well who want to get educated in order to further their access to economic opportunity. It’s an overwhelming landscape. So the workplace of the future is really changing rapidly. And what are the biggest issues that you see? And what are the biggest concerns that you see emerging with these changes? I mean, we obviously know that AI is a is a big deal. But that’s kind of like just recently on the landscape and horizon, what are they? What are some of the other core issues that you are trying to address?


Jessica Hinkle  06:17

Yeah, I think, Debbie, that it’s just the pace of change that is just accelerated so dramatically. You could definitely say that the advent of generative AI is really pushing on the accelerator of that. But I mean, this has been happening, as you said, for many years. And I think it’s really starting to reach a crescendo, where we’re realizing that continuous upskilling is just going to be required, you cannot expect that you’re going to walk in on day one, and never have to learn new skills again. It isn’t about just moving into a new job, it’s going to be your job is going to actually transform itself. A data analyst, for example, the role of a data analyst, historically, is completely different than the role of a data analyst in a generative AI world. There’s so much of that kind of ground level entry level work, that can be done automatically. So these roles are going to transform before our very eyes. And I think it’s really critical that we do have this tight connection between education and employment, so that we’re not falling behind in terms of what we’re teaching. And employers are not feeling so disillusioned by the quality of the, for lack of a better word, product that’s coming out post secondary education and training institutions.


Debbie Goodman  07:58

Isn’t it also vice versa, where the students going into higher ed are getting education that is just absolutely not equipping them for the needs of the workplace, both now and in the future. So I mean, even thinking about a four year Liberal Arts degree, whether or not it equipped anyone to do anything specific in the first place is a question. Nevertheless, it was considered to be the groundwork for a postgrad and further education and we know that it certainly equips a high schooler with certain skills that they may not have had before. But now just looking at the higher ed landscape, how quickly are they adjusting to the needs of the now workplace, not even in taking into account what the future holds, because we’re all a little bit sort of freaked out about what that might look like.


Jessica Hinkle  08:53

I think higher ed has been historically incredibly slow to move. I think what we’re seeing are higher ed departments like continuing education departments that really have a lot more flexibility in terms of being able to offer programs that are way more connected to kind of jobs and specific needs in a local market. But there has been just such an emphasis recently about needing to draw these greater connections and kind of move away from the ivory tower thinking of what a four-year degree is supposed to look like. We’re seeing some really interesting new models that are you know, starting to kind of piece together some more valuable skills and specific types of courses and majors that can be done integrated into a four year experience. So less of an either or, and more of both. And you know, I think that’s what excites me, is the players that are really thinking about how to work within the system, as opposed to how to just like, pick up and throw away an entire system of higher education that has been established for a long time, the system I think, can work hand in hand with a lot of these new solution providers. And there just needs to be a lot more flexibility. When you think about the way that a faculty senate approves programs, or the way that transfer policies work, to be able to be more accommodating and fast. That’s going to be necessary. And we are starting to see some green shoots of new initiatives that are very promising that I think are pushing in that direction. 


Debbie Goodman  11:03

Well, I mean, that’s good and very exciting to hear, and very necessary to hear. Because I mean, back in the day, you know, you’d finish high school, maybe get a four year degree, and then set yourself up for a job where you never ever needed to study anything ever again. You just went into a job in a company and got one promotion, and then maybe a little bit of onboarding at a new company in order to do something else. I mean, that is just completely unfathomable, that today, that would be the sort of course of one’s career and employment trajectory. We know that there are going to be these multiple, sort of detours along the way with the need to connect what you know, and how you work. And you’ve used the term job dislocation. And I actually wanted to dig into that, because the first time you mentioned I was like, well, I like that phrase. I love always hearing new phrases. And then I was like, I’m not sure that I fully understand that. So help me unpack that?


Jessica Hinkle  12:01

You know, when I think about job dislocation, I think about the fact that the jobs today won’t look like the jobs tomorrow. And you’ve really got these, these positions that nobody would have ever thought about. Like, I mean, did anybody know what a prompt engineer was two years ago? No, that’s a brand new career. And now we need to figure out how do we train people to be a prompt engineer? Well, it’s probably going to be quite a while before you have a full year program, a Bachelor’s in prompt engineering. But those kinds of jobs are necessitating this connection back to higher ed. So we, you know, we’re starting to see kind of this splintering of jobs into different categories in different areas. And we’re also starting to see jobs that maybe kind of historically, you thought were really only appropriate for one industry start to really move into another industry. So when we have been really concerned about the reduction in tech hiring over the past year or so here, there are actually a lot of tech jobs in banking and insurance. And so there you’re really moving individuals who have sets of skills from one industry to another. So I think, again, being able to have that flexibility of the way that we think about and define jobs, is going to be really critical, because we really need to identify the skill set and the experiences that can be transferable into whether it’s a different function, a different industry. And this is going to be critical as you have economic slumps in one industry, and you need to figure out how you’re going to pivot to another.


Debbie Goodman  14:06

Okay, so I just wanted to park on this point around AI skills. Because where we are now, is we know one thing for sure, is that people with AI skills are going to be better off, more in demand, more valuable than people without AI skills. So I mean, we don’t know necessarily how the future is going to play out, but I think we can take that as a statement of relative truth. Even if I made it up myself. But AI enabled people who are knowledgeable about how to use the technology, for sure, are going to be more valuable to an organization than people who don’t know how to use the tech. Knowing that, are organizations, be it boot camps or higher ed institutions or any of the in-between, already starting to engage with workplaces in order to understand what needs are, so that they can equip students with those skills? Or is it kind of expected that people will just acquire this knowledge when they get into the workplace? Do you know how this is being addressed right now?


Jessica Hinkle  15:13

My sense is, and again, this is moving faster than the speed of light. So I think, you know, last November, nobody even knew what open AI was. Right? I had no, I’d never heard of it. And then suddenly, there’s a ChatGPT explosion over the past 12 months. What I do think is that there has been a clear adoption, both by students and by individuals, to just go with it and just try it out and incorporate it into their everyday life. And so I think that, you know, when you talk about AI skills, it’s almost like Google Search, right? Like, this is just something you would never say, like, well, I’m highly skilled in Google Search and you know, I’m really good at finding information on flights through Kayak. This is actually just something that has become just part of our DNA, right. And I see generative AI in the same way, there’s going to be the expectation that you’re going to use it in order to advance your work one stage, and whether that’s doing it inside of your classroom so that you can get ideas and, you know, help to brainstorm first drafts of papers that you’re writing, or whether it’s in the workplace where you need to write a memo and you need to put together a series of prompts to be able to have the memo clearly articulate through generative AI what you want to express, this is going to make everybody’s life easier. So I think that it’s, you know, it’s less about this fear of using generative AI and I think it’s more about this embrace of how it can make my life easier. With that, I will say that the most important thing is going to be that you can’t just take that at face value, right? You have to look at it, you have to have full analysis of whether or not this makes sense, whether or not this is consistent with what you’re trying to express. And, Debbie, then it goes back to those Liberal Arts degrees, right, critical thinking skills. Yeah. And that’s where I think that higher ed has a place to shine again, where we can stop with the ‘either or’ of higher ed, and liberal arts or degrees that are skills based and we can get back to an ‘and’, where really what you’re learning and gaining in higher ed is the ability to think critically, to question, to be able to put forth an argument and think differently.


Debbie Goodman  18:12

Yeah, well, thank you for bringing that full circle. I was kind of playing devil’s advocate there. But um, so great to really bring it back to when we’re looking at the connection between new technology and the base underlying skills that we need in order to utilize this for future progress. It’s definitely an ‘and’, or ‘both’. And I’m interested to know, of all the new investments that you are seeing, all the new sort of entrepreneurial initiatives, the new companies that are emerging that are potential investments for you, what are you most excited about right now?


Jessica Hinkle  18:59

I am really excited about the companies that are working in combination with and not against established system players. So I think the reality is that when you look at organizations that are training providers that are trying to put forth a new model for education, there is an entrenched, higher ed base that is really going to push back on them. To the extent that we’ve seen companies that are really working in concert with the higher ed providers, we believe that that’s where you’re going to start to see the transformation, both for the companies and for the individuals that they ultimately serve, and for the way that the higher ed institutions start to think about their own organizations as businesses, right. I mean, so I’ll give you an example. We’ve got an investment in a company called Upgrade education. Upgrade works with community colleges to offer certification, alternative certification programs in tech fields. So these are kind of short, three to six month programs. And community colleges are their channel. So community colleges have this local connection to the community. They are providing the credibility and gravitas of the institution. Yet they’re offering a program that will help to provide skills and preparation for jobs and be able to lead individuals into a career. That’s one example of a company that’s really saying like, I really need to think about partners, who are the partners that can help get me access to the market. The other benefit of community colleges is that they are, they’re often the entities that are able to access federal funding from the Department of Labor, so that individuals can defray the cost of these alternative certification programs. By taking the programs through these community colleges, these are some of the interesting models that we’re excited about.


Debbie Goodman  21:24

Does sound really, really cool. I mean, in some respects, I always say if I didn’t do my job, I’d kind of like to do your job, because I’d love to know what’s new, what’s shaking up, what’s happening you know, this the market right now. I mean, we met up at Edtech Week in September and it was great to see some of the emerging companies and emerging entrepreneurs, but also what was very prevalent to me is how bleak the fundraising market is right now for up and coming entrepreneurs who are really struggling to raise capital, be it at any stage, whether it’s pre-seed, seed, A, B. I mean, it’s a struggle, no matter which part of the funnel you’re in. What message would you want to share with particularly social entrepreneurs, who have both impact and profit at you know, they’re looking at both of those things. And it’s kind of baked into a lot of companies in the tech space. They’re still in the fundraising phase or the early sort of phase of product design. What would you want to share with them as a message for like heading into 2024?


Jessica Hinkle  22:43

I think what I would say is, if you’re a social entrepreneur, and you are really committed to how your solution is going to deliver impact, you really need to build outcomes thinking into your business model from the start. This can’t be something where you say, oh, and after the fact we’ll figure out whether or not our product improved persistence or retention, or helped to deliver better economic outcomes to individuals. This has to be something that you really establish as you’re thinking about the product that you’re offering, how you’re delivering it, and who is the end beneficiary. So there’s an intentionality that I think is really critical. People throw around the word impact all the time. They talk about outcomes when often they’re really actually just talking about outputs, which is one of my biggest pet peeves. So I, you know, I would say, if you if you’re really committed to developing a solution for this space, you want to to be focused on how you’re going to deliver change to individuals, how are you going to transform individuals lives and try to stick with that. This is a really tough market and I think you need to think very, very carefully about who you’re selling to, and whether your solution is going to cut through the morass of ed tech and workforce tech and HR tech solutions. Buyers are overwhelmed. They’re overwhelmed with point solutions that only solve one piece of the puzzle. And so those organizations, whether it’s in higher ed institutions, or post secondary providers, or employers, they really want to have more kind of platform opportunities to look at, so that they aren’t trying to figure out how your point solution fits into their puzzle. Organizations that have really thought about strategic partnerships that kind of leverage strengths across multiple companies are starting to be pretty exciting for us. Another company that we invested in called Upswing, is focused on doing this with a company called Bettermind. So Upswing is a student services platform that offers tutoring and helps direct non traditional students from community colleges and regional public universities to the resources that they need on campus. And they partnered with Bettermind to be the channel partner, for Bettermind offers online mental health therapy to college students. So it’s just that kind of thing. It’s a perfect way to integrate to early stage companies that are both trying to target the same buyer with a solution that’s more comprehensive, without kind of compromising one company’s vision for another company’s vision. Right. Just thinking more creative about venture partnerships.


Debbie Goodman  26:05

Yeah, that does sound like a perfect match and a great solution for actually all the stakeholders. I’ve got one last question and maybe it’s hopefully a message of encouragement, but who knows? Here goes! So we know that 2023 was a pretty tough year for the market, for the ed tech market. What do you predict for 2024? Are we going to be still sort of groveling on our bellies through a dark tunnel? Or is this light at the end of this emerging in 2024?


Jessica Hinkle  26:41

Oh, that’s such a hard question. I think 2024 is going to be hard. And I’m a Sagittarius, so I have to be an optimist. But okay. The parental realist in me recognizes that 2024 is going to be a massive year of consolidation. And, I mean, we’ve been seeing it in the second half of 2023, we just saw a huge announcement within structures, acquisition of parchment, those kinds of things we’re really going to be seeing. I talked to a number of fund managers that are really thinking about platform plays really, really interested in buying one company in a space and then bolting on other companies into that platform, and then being able to have a more substantial and meaningful offering to the the clients that they serve. And I just think that that’s really what we’re going to be seeing a lot of, so those founders that get more creative themselves with these strategic partnerships, and even founder led mergers, where, you know, they’re kind of talking to like-minded peers and saying, you know, we should really come together because it is it’s just too challenging a market to try to cut through the noise all the buyers are dealing with.


Debbie Goodman  28:09

Okay, well, I’m just going to take that as a message of hope and optimism around creativity. Because ultimately, entrepreneurs are innately creative beings who are always looking to make something out of nothing, and constantly pivoting and challenging environments also do present new opportunities. And so that might not be necessarily in the direction that one had thought at the outset. But then frankly, it never really is. So, another year of ongoing creativity in 2024. Jessica, thank you so much for your time. It’s been a pleasure to talk to you and all the best for the rest of this year and into the new one.


Jessica Hinkle  28:48

Thank you so much, Debbie. It’s been such a pleasure to be here. I appreciate it. Bye now.


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