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Jennifer Byrne is the CEO of Arrived Workforce Connections. Previously Jennifer was responsible for market expansion initiatives leveraging business model and technology innovation for government, healthcare, and education providers around the globe at Microsoft after joining as the Chief Security Officer for the Worldwide Public Sector Division in 2014.

Prior to Microsoft, Jennifer was a leader in Cybersecurity, having held technical, sales and executive positions at companies such as Intel, McAfee and Symantec. She began her career in technology as an Information Security Analyst and Engineer serving US Government clients.

Her first career, which remains her passion today, was in the non-profit world working with under-served populations.

We discuss how to use tech innovation for optimizing the human experience, the importance of tech access to underserved communities, and how we can all do something small every day to make a difference. 

Thank you and congratulations to Jennifer on her new role as CEO!

Transcript powered by Happy Scribe

Welcome to the show. My name is Eric Wright. I’m gonna be your host for the DiscoPosse podcast. This is a really enjoyable episode featuring Jennifer Bryne.

Jennifer. Between the time we recorded and now when we released, we can proudly say that we can say Congratulations to Jennifer on becoming the CEO of Arrived Workforce Connections. Jennifer has such a storied history in the industry, but more than anything, the reason why she’s been successful both in work and in life is because how she gives back in her approach to thinking about what can we do to give, especially to underserved communities and to the broader community.

This is a great discussion and we cover a lot of ground. We didn’t get a chance to go specifically into her new role as CEO because it was in the works and had not yet been announced when we recorded. So big thanks to Jennifer for giving me the chance to record while she’s in the throes of transition. And Congratulations again. So please do follow the link and reach out to Jennifer and give her a good shout out and a Congratulations. I got to give another shout out.

Speaking of, to the fine folks that make this podcast happen and to really celebrate a fantastic year we’ve all had together. So remember when you have anything in the world of data, in the world of compute, in the world of cloud, you need to protect those assets. How do you do it? Go to the people that have you covered for everything you need for your data protection needs, whether it’s On-Prem, whether it’s in the Cloud, whether it’s Cloud-Native. They’ve got stuff for SAAS, they’ve got your team’s protection SharePoint. You name it.

It’s really important because if you can’t go and say I got Veeam, they got me covered. You’re at risk. No risk equals a great world. If you can reduce risk, it’s easy to think that you’re in a better place. So let’s reduce risk together. Go to vee.am/DiscoPosse. You can check it out. They got a really cool campaign running, but I really and truly enjoy the team and I love the products and I’m very proud of the way they’ve approached things and they got a brand new CEO.

So let’s celebrate this together. So go to vee.am/DiscoPosse. And while you’re protecting, make sure you protect your data in transit as well. If you’re not using a VPN, you definitely need to think about why this is so important. We’re in a dangerous world. Let’s make sure we reduce the risk exposure when you’re surfing the Internet. Whether it’s out in the world or even at home, go to tryexpressvpn.com/DiscoPosse. You can check out ExpressVPN. I’m a user. I’m a customer. I really like it. So go check it out.

Oh, yeah. And buy Diabolical Coffee. All right. Enjoy the show.

Hey, this is Jennifer Byrne. I am the President of Digital Future Consulting and the former CTO of Microsoft US division and about to start a new venture as the CEO. And you are listening to the DiscoPosse podcast.

Jennifer, thank you very much. This is very exciting for me for a variety of reasons and, of course, for my listeners. But selfishly, I think I really do the podcast just so I can meet amazing people like yourself. You’ve got a really strong sort of storied career. You’ve done stuff that I find really inspiring in your approach to the way that you treat people, the way that you empower others, the way that we can use technology. And you talk so much about empowerment through technology. And this is near and dear to my heart because I’m a nerd at heart, and I love technology, and I love the Nerd Bits, and I love getting excited about it.

But I also have to see that what really gets me is what we can do with it. And so we’ll talk a lot about the path to digital transformation and the human empowerment that we can create along the way. But anyway, let me first of all, for folks that are new to you. Jennifer, if you want to give a quick introduction, and then we’ll talk about, first of all, digital future consulting and of course, much more that you’ve got going on.

Yeah. Thank you. Eric. I’m excited to be here, too. This is why I love to be on podcast because this is when you get to talk about all your favorite topics. So the big anchor in my career was the years I spent at Microsoft as the CTO, ultimately of the US division. Although my first CTO role at Microsoft was in the industry team, and I joined Microsoft in 2014 as the chief security officer for the public sector group. Because I’d spent the previous 20 odd years in cybersecurity at Intel McAfee Symantec into startup and way back when I was an InfoSec analyst working for government agencies back in the late 90s.

So that’s my career. I left Microsoft when I had felt like I’d put in my time in big corporate America and felt a calling to do something a little bit different. I had run a couple of innovation projects in my last role as CTO focused on digital skills, and it really started out really simple because we needed more people to know how to use Azure. You cannot drive cloud consumption when there aren’t enough employees in your customers environment than no Azure. But you start to pull the thread on that one, and it’s really not about Azure.

It’s about the skills that you need in order to learn Azure. And then it’s a bigger skills conversation. And all of a sudden, you’re outside of the walls of your customers environment and you’re into communities thinking broadly like, how do we get skills to happen? Because the world is getting more digital and you don’t know that any better than you do when you’re in this industry trying to make that possible. And then it just kind of occurred to me as I’m sitting in communities like Louisville, Kentucky and Houston and Syracuse, New York, that there is this unintended consequence of technology that I think, Eric, you know, and all of us who have been in this industry, we’ve been in the business of talking about how amazing technology is and all the fantastic things they can do in the world, how many problems it can solve.

And it is largely a positive passion that we all believe in. And yet the unintended consequences that it creates a need for skills that a lot of people don’t have. So how do we solve that? And by the way, that skills gap follows socioeconomic, existing socioeconomic rifts in society. And so it is a problem that takes more than technologists to solve. But it felt like a worthy thing to be doing. So when I left Corporate America, I decided I would spend a little time in the future workspace.

So I started a small consulting agency and I work with startups and advise companies. And that’s super fun. It keeps me fresh and also spend a lot of time just doing research and talking and thinking about future work, which has led to a role as a CEO and a company that is playing a small role in that space. So anyway, that’s the nickel tour around me and my career.

Well, there’s so much to, so many threads to pull on. And I think you hit this really strong thing that especially as technologists, where it’s a bit of a bubble. I get concerned about the echo chamber of raw technologists who are all on Twitter, and they’re all at the events. And we all sort of like chatter amongst each other. And that’s fantastic as a way for us to kind of like, build new things. But for people that don’t know what SoMa is in the Bay Area, and there’s so much of this country and of the world that’s beyond the very tech centric Silicon Valley, the New York Bank sectors, like all this amazing stuff in between.

As a technologist, I would go to events, and I would talk about how we’re into other areas, right? I go to Wisconsin. This is one thing that was amazing to me. You go to Wisconsin, there’s these incredible technology companies. And at first I was like, just like the stupid, arrogant guy that lived in the city too many years. I was like, That’s funny. Whenever I reference Wisconsin, I always think of like a dairy farm or something like this, like people with cheese hats.

By the way, that does happen in Wisconsin.

But it was humbling to realize that they have really done leaps and bounds of advancement in how they’re leveraging technology to do a lot of these flyover state things that the rest of the tech ecosystem kind of forgets, goes on. And I was happy when I realized I’m like, this is what matters. These are the stories that need to be told, not how I can get Bank of New York Mellon to go from VMs to containers. That’s neat. But when I can talk about people that never worked in tech suddenly becoming programmers and using no code and using the cloud.

And they were from all sorts of diverse backgrounds. That’s the exciting part to me. And I love that you’ve done research in this area as well, and you’re really working hard to broaden your audience.

Thank you so much. I love what you said about Wisconsin because the specific epiphany I had, and it happened in Louisville, Kentucky, when I was at a ribbon cutting event for a makerspace. It’s like a nonprofit and they renovated it, and they created these conference rooms, and they were really just in the business of helping very small entrepreneurs build the things that they wanted to build. And I had this, as a Microsoft executive, you’re there to stand at a podium and say kind words. We’d sponsored some of this.

I loved the project, but we give them some dollars. That was really, some total of what we did was lend our name, our credibility, give some dollars. I flew out to Louisville, and that was what we were going to do. And it was so clear to me that that was actually just in the broader context of things. Such a small contribution to the grander picture of a really healthy, inclusive digital future because the real work was being done by the people in the facility. The real work happens at the ground floor on the street level.

And I was spending all my time on the 28th floor of a beautiful building in Bellevue, Washington, thinking about programs and thinking broadly and top-down. And I got all the attention. I got all the attention, but I wasn’t really the solution. So when you get down to the street level, if you’re in Wisconsin and people have real problems and they’re vary from a technologist perspective, they’re great problems because they’re discrete problems. They’re bounded. So you can attach technology to a problem at that level and actually generate a difference.

The distance between action and reaction and a small problem is very short. The distance between action and reaction and a really big macroeconomic or global problem or something that would be worthy of a corporate initiative is very long. So if you want to measure impact, then get down into the street and start doing stuff, and that was really when I thought, okay, I can see how this stage of my career could come to a really wonderful and positive end. And I could have the beginning of something else that would be fulfilling for me and also just measurable enough for me to feel like I was making a difference.

This is the interesting dichotomy of, as you said, becoming sort of the face and voice of technology and transformation and all these things. We have to have the evangelists and the advocates and whatever the title is going to be next year when we’re no longer developer advocates are no longer cool. Whatever the new thing is going to be. And it’s this weird thing that I sort of struggle with all the time of being able to get out and meet with people and listen to them. When I do a keynote, it’s to listen to 500 people, to watch their reaction as we’re talking about something and change the way that I tell a story and change the way that I look at what’s next based on that live reaction.

Plus, after the fact we get to talk to people on the ground and you really hear what’s true. It’s very easy to get this Ivory Tower super presenter mode in. But now the advantage you get is pairing that opportunity where you can write books and be a speaker and do all these things and do the ribbon cuttings and then also really be mindful and humble about who’s really doing it. Like you said, this is the true sort of boots on the ground, the unsung heroes, the real transformation is all these other people.

So it’s just weird. I feel bad sometimes, in fact, a lot of friends of mine that are in the public speaking space, they’ve chosen just like to stop. We need to open the stage up for more people. The hard part is when you’re good at public speaking, you get asked to do more of it, and you’re sort of stuck. Like, Why is Robert Downey Jr. In a lot of movies? Because he’s a great actor. So is it his fault? I don’t, not that I’m Robert Downey Jr., for a poor example.

But I mean, I love that you’ve been able to strike this beautiful balance of being close to where it’s really happening. And I find people that have trouble. Sometimes they get a little hung on the idea of looking down from the stage.

It’s tough to find the right altitude. And I will say in defense of good speakers everywhere, that we all have to move forward together. And so it’s the three-legged stool analogy. Two legs just won’t do. So we all have to be doing all of it. And by the way, look, I’m in your podcast. I love to talk about this stuff. So it’s the daily drip of being able to talk about the things that matter, and hopefully in a way that’s helpful to other people is important for me, too.

When I got out of Microsoft and you just do a bunch of stuff and you’re trying to cycle through what I realized I was doing eventually was trying to find the right altitude. I didn’t want to just talk about the problem, but I didn’t want to get so down into the weeds that I was lost in something that felt like a passion project but wasn’t going to create some kind of impact on the world. And so then you sort of get into the problem space you’re in, what does the ecosystem look like?

A tech background really helps because it’s kind of a design thinking or systems approach to things where you’re trying to understand the inner work I was in the future workspace and am and thinking about how do we democratize access to skills, but also how do we change the power structure such that people themselves have the ability to leverage the things that make them better if it’s a skills course or whatever, into a better job, because that’s not how the job market works. It’s very top-down.

So if you’re at the bottom, you just wait for jobs to come to you by way of a job advertisement on Indeed. So if you want to go invest in yourself and get a new skill, it’s a really uncertain business model, right? I mean, that’s not how people think about it, but if you’re a business person you’re like, I don’t understand the ROI of that. That course is going to cost you $12,000 in a year, but you have no actual guaranteed return because you have no way of proactively advertising yourself.

The only platform that exists for that is LinkedIn, which is fabulous, but LinkedIn from a demographic’s perspective is the higher end of the job skills, sort of like in healthcare, treating what they call the worried well, the people who are already healthy and they just want to get healthier. Like LinkedIn is a proactive profile building platform is for people who already generally have a job and they want a better one. But we have this whole section of the workforce that doesn’t. They’re just struggling to get living wage who are very interested in building capabilities and experience that will provide a better path of the future.

But we don’t have a path for them to do so in a proactive way. And so that was when I started to understand in this skills job space what the ecosystem started to look like, where the power was, where the connection is, and then from there, you can figure out, okay, what could we do from a tech perspective to solve that? So that’s all my long, winding way of saying for me, I had to figure out what altitude I could be relevant in this process, and it took a year to get there.

What I respect about how you just described it and your approach to it was just that you have to take a hypothesis. You have to test the hypothesis. You have to live amongst the results and then bring that back to the hypothesis and effectively run it through this machine. And that’s really what makes, it’s very easy for the, I’ll say the pundits, as I call them, right? That it’s easy to sit back and talk about the future of X, but yet never be committed to saying this is how it’s going to go and then writing it down and saying, I’ll pay $1,000 if I’m wrong, like, you’re effectively skinning the game committed to the outcome because you are getting close to who will be affected by it. You’re looking for, especially a population that’s, like, under represented population.

It doesn’t even have to be such a sort of distinct niche. It is 30 plus percent of the United States as an example, and I’m Canadian. My funny accent gives me away sometimes, but I live in New Jersey. There’s so many people who, like, we take for granted. And I say we meaning the Twitterati, right? We’re complaining. Everyone’s talking about the great resignation, and it’s a proud thing. I’m like, yeah, that’s right. Because people are saying, like, oh, it’s disgusting that they’re going to make me go back to an office.

Did you go to Whole Foods today? Yeah. There’s 1000 people, that’s their office. Those people that made sure that you got your well crafted latte and your fancy artisanal steak. They don’t have a work from home option. We have to remember that as a community, it’s not just the community of, like, it’s the community of existence. It’s so easy for us to get just wrapped into, like, oh, yeah, Linkedin is for everybody. I love LinkedIn. I love that it’s a great tool, but it’s very easy for us to just say, like, oh, this box is the Earth.

Right. Yeah.

Totally. You know, I agree. That’s the challenge. It’s a big challenge. It feels like something that could make a difference. And I love when I see my own peers trying to solve the technical aspects of that problem. And many of them are whether that was the intent or not. Microsoft isn’t the only company. There are many that are trying to. IBM, as an example, are trying to democratize access to technology by abstracting the complexity out of it, which is the inspiration behind low code, no code, the abilities or capabilities and whatever platform you’re in.

And digital skills. All the companies are spending a ton of money to try to solve that problem. So I think it is something that we broadly recognize as an issue. The problem is that it is an issue that’s so intractable in its nature because it’s embedded into the kind of the economic structures of our society that you just need a lot of creativity and effort to make a difference. And, you know, I have two kids in their twenties. My daughter is an aspiring artist and works at a restaurant, and it’s tough to watch it.

My son is in his last year as a computer science major, so he’s figured out how to have a career that will pay money. But I’ve got an equally bright, hard working kid who didn’t make that choice, and she’s going to have a tougher road. And I see from her first hand how the world is not built to serve her in her needs given what she wants to do with her life, and that’s okay. Like she made her choices eyes wide open. But there’s stuff that we could fix that would make it better.

And it’s just not about handouts or anything. It’s really just about rethinking the problem in a new way. And if you can make your society healthier, everyone benefits, it is a shared infrastructure that we’re in after all. So that becomes very personal to me on that level. And trying to figure out how to solve it becomes super important.

Yeah. There’s a real challenge in that. The business world, especially the tech startup ecosystem, is very driven on quarter over quarter measurement and growth. But to have the long view, this is why philanthropy and corporate don’t line up in the pure money sense they often can, because it’s a tax deduction. And at least we’ve created a way in which that it can incent people to give back in that way. But what we really need to do is create programs and put people in front of people and show them, that story is there.

I think democratization is a great way to talk about it now. Like you can become a Twitch streamer and you only need to just do the thing that you did, right? It’s the potential is there, that is something like that. You can go on YouTube, you can learn to program through. You can take Harvard Business School courses on YouTube, right. We’ve created opportunity like as far as content and tech access, although Internet access is still not 100% available. Right. But connecting people and giving them a path.

I think this is what’s missing and like mentorship. So I’d love to get your thoughts on this. What have we got today that’s not being used, right? Because we haven’t connected people to show them how to embrace and leverage it.

Yeah. Well, I think it’s a slightly different problem depending on industry. And again, this goes back to your Wisconsin comment that we all think we understand that the edge of the horizon, as we see it, is the actual edge. And it’s not right. We all live in these universes. And so that question for people who are in whatever space where they can move toward Tuck In at Varleys, in the way we would describe it. Computing, right. Coding all those jobs is when there are things that we can do there.

And I think it has a lot to do with a bigger corporate investment and nontraditional learning skills. We could dissect that problem, and I’m very interested in it. There’s a job taxonomy of the future, piece of work that needs to be embraced by the Fortune 500s and 1000s so that HR and people managers recruiters can understand what they’re even hiring for, because once there’s clarity on what the job of the future looks like, there’s clarity on the skills required for the job in the future. And once you have that, you can start to rewrite job descriptions.

You can start to think about the way you recruit. You can start to signal out to potential candidates what they even need to do in order to be eligible for that job in the future. And I think that will sort itself out because you get smart people in that swath that understand the problem and can solve it. But there’s this other technology conversation that it’s easy for computing technologists to forget, which is that in a factory, automation in a factory means that somebody who is actually doing knobs and levers on a control panel is going to move to an iPad, and that iPad is going to require some level of digital context or fluency, that for you and I, might not be the biggest deal, but for people in industries, it will.

There’s a lot of manufacturing and light industrial that works on paper today because they haven’t had a business model to do anything else. Like the solutions factory, light industrial is really interesting if you look at it as an industry, because it’s a very long tail industry where you have a few companies that are big, but most of the revenue or a lot of it is driven through small, independently franchise. If you will branch factories or installations or smaller companies because they are providers to bigger companies, they don’t have a business model for adopting technology.

They don’t have the revenue to do it. And so it exists on paper. But as that automation flows down, you’re starting to require workers to have a level of digital skill that they don’t have. So a manufacturer of a conveyor belt technology that gets put into a factory might require a certification to use that technology. The certification, if you had, it might actually allow you to go find a job that pays $3 more an hour because it’s a little bit more advanced. That scenario exists in almost every industry and that’s technology, and those are digital skills and their digital skills importantly, that once obtained, actually provide a path toward a better living wage.

So for me, that’s the part of the problem that I’m most interested in. It’s ignored. And yet we’re talking about the people who, in aggregate, are the lifeblood of our economy. They are the people who make things and make things work. To your point, the folks in Whole Foods or the people solving real problems in Wisconsin. So I’m interested in that technology and how we help that profile of worker.

Yes. And I probably sound like a dark individual sometimes how much I sort of trash the peer group that I live amongst. But this is just because sometimes it bothers me that they don’t see beyond the rather often myopic view that they have of their frame of existence. And fair enough, it’s not even intentional. It’s just more that when you get people that are very outward about like this is what the world looks like. That’s what your view of the world looks like. It’s not really representative. The whole sort of learn to code as this trope of like, oh, that’s the future of work.


You need to learn to code like, no, it’s not possible for many people. I’m a technologist. I have a whole host of things that I probably would have had to take pills for when I was a kid ADHD and all this different stuff. And I’m also dyslexic, so it’s horrifying for me to write code. I do it, but more out of necessity. And I live with a wealth of anxiety while I’m doing it. And I have skills that most people never got exposed to. You know, I always say I grew up on a farm and I became a technologist, but that’s because my dad was a technologist who took the leap and got out of the farming and made this jump.

Most people don’t have that luxury to leave their ecosystem or their geography. They can’t leave where they live. There are a lot more limiting factors that are forgotten. I think sometimes, which is a little bit frustrating.

Agree. It’s a big problem. Anyway, it’s a lifetime of work. So I’m in an area where I don’t think I’ll ever run out of interesting things to talk about and good stuff to do. So Yay for me. Good job security.

That’s right. What’s a good example of something that you’ve really seen that strikes home, it’s like this is the power of people getting access to technology that you’ve recently seen that’s excited you.

Well, I mean, I haven’t seen it yet in the space I’m in, which is why I’m in the space I’m in, kind of thinking about the other industries where this hasn’t happened. But I’ll tell you, I follow a lot of nontraditional education providers, and I listen to their stories is kind of my daily good news. And so companies like General Assembly and there are many others, have a constant stream of success stories where people have made the leap from whatever they were doing that was not satisfying into jobs that are and, of course, those are tech jobs.

But I think it’s fantastic. So I think it is actually happening all around us. And if there weren’t a ground swell of that, however, the media may or may not be able to report on it. It’s a harder thing maybe to report on. I think it’s behind a lot of this great resignation, which itself, I think, is fantastic news. And it’s happening because people are looking around and they’re seeing their friends and their family or their peers make a leap and all they needed. It’s like all the little penguins are standing at the edge of the glacier, and they just need one of them to jump and everyone else is kind of following.

And I think that’s starting to happen. That’s behind the groundswell and the very fact that there is this great resignation, the very fact that people are, it’s kind of a take back the night moment are starting to say, yeah. No. I mean, sure, I had my unemployment benefits are out, by the way now, and I’m still not going to go back to that crappy job. Sorry. I’m going to figure it out, is exactly what is at the birth of any big social change. So I’m excited.

And, of course, because of my kids, I hear it all the time. I hear my daughter say, if you use the word gig one more time, I’m going to die. We know what that means, and we’re demanding something better. So I think there’s good news, even in the bad news, because it means that people are going to sort of accept, not stand for accepting less. You remember 20 years ago, the issues with the big box retailers, where there were all sorts of lawsuits and generally speaking, I think we all had this collective sigh like, oh, yeah.

It must be terrible to have a part time job in much of America because you don’t get your hours published. Even today. Did you know that they’re, like, 26 million workers who do not know their schedule more than a week in advance? How do you live a life when you can’t figure out what you’re going to be doing next week?

Yeah. When the alternative is you need to find a second part time job, but they’re constantly conflicting or you’re always up in the air. I remember the early days of working two retail jobs, and on Sunday you would find out the schedule for one. And on Monday, you’d find out the schedule for the other. And then I’d have to race to see if I could get shift coverage. And that was just me for part time jobs. But I was in school, so it didn’t hurt me. There are people that have families, but that’s their reality.

And it’s easy to forget sometimes that’s just so much millions. The sheer numbers. This one thing always boggles my mind is that if you just look at the sheer numbers, it’s very easy to lose track that, well, 300. That means that 307,000,000 people don’t have that problem. But there’s 26 million people that do. That’s a giant number. We should all be a little bit horrified. I love the great resignation from the idea. Somebody on not too long ago is Michelle Seiler Tucker, and she’s focused on helping people to build their business for sale, to how to get out of the business and make it viable for purchase.

And she goes through this whole program. And she says, the funny thing is we have these weird stats that we hear all the time that are like, 90% of startups fail and all this different stuff. And she’s like, Well, we’re actually lying when we say those things because according to the Small Business Administration for the past 24 months, in fact, 75% plus or, I forget the exact number of businesses, are thriving. And in fact, businesses that are more than 20 years old have a 90 plus percent failure rate.

So it’s actually the reverse that those of us who are like, I’m done, I’m going to build my own thing. I’m going to do my own thing. We are the next generation of statistics that haven’t been realized yet.

Well, as somebody who just took a CEO role in a company with not that many people in an early stage in market, but just barely, I am excited about that. That’s great. My odds are better than I thought they were.

Yeah. It’s an unfortunate trope that we take this old thing. It’s the same way that, its possession is nine tenths to the law and all these goofy sort of stats that we get tossed around almost like fortune cookie sayings that become wrong quickly, but they’re still printed somewhere. So we still call on them. I love this idea that, I’ve even seen through my own company that people that we hired as business development reps and BDRs or SDRs, their cut in basically dialing for dollars people, right? Like, they get on.

Like, they get on. They’re doing cold calling. And you see someone, you like, oh, he seems different, right? I couldn’t figure out this one seemed like he’s got something going on. And then I see him in LinkedIn, founding a new company. I’m like, oh, that’s neat. Then I see him launching a series A. I’m like, oh, yeah, that’s there. So what you’re creating now, Jennifer, is that small group of people. Those are also future founders that you’re probably empowering because they’ve seen that it can be done now. That’s magical to me.

Yeah, I think so, too. I think it’s exciting. We’ll see what that looks like in the future. If it becomes a competency to build a company. I don’t know how that works from a kind of macroeconomic perspective, but for sure, you do see your point around monetization, you do see so many more people thinking creatively about how to monetize themselves. So sometimes that shows up in our world as the founder of a tech company. But Twitch streaming the long tail of social media advertising. I think that it’s harder than it looks.

But there are a lot of people who are starting small businesses and figuring out how to effectively run them through social media platforms, which I also think is exciting. Upwork, Freelance. There’s a dark side to all those stories, but there’s a positive side to it as well that we’re starting to have a more distributed notion of what work looks like that not everybody has to work in a big company for the rest of their lives in a single career. We can do different things. So I think that’s exciting.

Yeah. And this is actually interesting that you brought that up, the idea that there is a dark side to many of these things as with anything. The hard part is that we’ve got such rapid access to that side of the story much faster than the good side. I remember when I was in Toronto and Uber was making its way into the city, and I was a nerd. I was like, that is really exciting. I can just get a car on my phone. It’s like, super cool. The people at my company, I worked at Raymond James at the time.

So I’ve got all these people that are running an investment firm, and they’re like, what is an Uber? They had no idea what I was talking about. I’m like, watch this. I hit a button and then Yukon XL pulls up on the road and door opens. Hop in, guys, we’re going to the party, and we would have this idea of, the disruption of it. And I was excited by the opportunity for disruption. Unfortunately, there are people that were not going to do financially well through it, and they would be facing challenges when it came to City Council trying to regulate it.

What ended up happening was you’d have, of course, very strong voices on either side. And you would hear people who would say, like, I’m a mother of three kids that are under six. I can get my mother in law to help me watch the kids from 09:00 p.m. Until two in the morning every night, and my husband takes care of them in the morning. So result, I get to work 5 hours a day and I make money and I feel safe.

You hear stories like this, it’s like she can’t work for a taxi. She can’t work at a regular job because it requires four till ten shifts. All of a sudden, we’ve got this incredible story again, counter. There are difficult sides of it as well. But like that opportunity, like Upwork and those opportunities now are there. I’m excited by it. But I also know that a lot of people don’t often see there’s risk and balance to kind of any new thing that we take on in this style.

Well, I think another way of saying that is that if you’re in the business of creating disruption, which is what Uber was in the business of doing and Airbnb and has become the North Star or the greatest aspiration for anybody who’s trying to be a founder of a tech company that matters, then the measure of your success may be that you cause so much disruption. You actually create unrest at social policy levels. Because I’ll tell you, I was at Microsoft when all that was happening, and I was traveling around the world talking to a lot of government leaders and ministries of finance in smaller countries.

And they wanted to know, like, the big question was Microsoft, what is your view on the uberization of work and technology. And what is the role of a tech company in that space? Because after all you’re creating a lot of this, and it’s actually causing a lot of unrest, especially in countries that have a little bit bigger of a social safety net and therefore more investment and a sense of responsibility for dramatic shifts in the way industry works. So it was a big thing to your point. I kept thinking, Well, this is a hard conversation, but if we just take the longer view, it’s probably going to end up in a good place because we are trying to solve the next generation or the next version of our problem.

But we’re making progress. There are as many success stories here as elsewhere. And let’s not forget that if you at all believe in free markets or in the wisdom of markets, there’s a reason why Uber was successful because they addressed an unmet need.


And it wasn’t even a technology, if you think about the components of the technology behind Uber, that’s not where the innovation was. The innovation was in the idea. And so personally, that’s my inspiration. If I want to go do something, of course, I want to be disruptive and make a big change. I’m not thinking I need to do it in technology. There are other technologists who will go be CEOs of companies that are in Cleantech or doing something crazy cool with AI. And that’s not me.

I think from an innovation perspective, you can just innovate by thinking of a fresh solution to an old problem and bring all the existing tech that already exists to play. And if you’re lucky, people get really uncomfortable. But you’re also making life better.

Yeah, because you hear it all the time. Like, these two sided markets are incredible. Their right for disruption. Next door really became a thing. It quietly was worth all of this money because it had such a vast growth. I had never heard of Nextdoor in my life. My mother-in-law. She’s like, I’ll go on Nextdoor and find something. We’re looking for a contractor. I’m like, what the heck is Nextdoor? Then I dig into it. I’m like, Good golly. This thing is worth billions, but it was just that, right?

A two sided marketplace. You had people that need to be serviced on either side. This is fantastic. Everything needs to be like, all it takes is a little bit of an idea, and you can close the gap. And what it satisfied for me was, I solved the problem. I needed to get a hose fixed and somebody else solved a problem. He’s trying to build his cottage and pay for his family. And so he found a little tiny gig that he could fit in in an afternoon.

And I didn’t need to write an ad in the paper for it. We’ve come a long way, and it’s magical that we can create this opportunity. I think I’m with you on Disruption. Sounds like a dark word sometimes, but it really means that in the same way that forests naturally will burn from that, you can only get new growth because if the forest continues to grow, it creates shade, which stops growth below the shade line. But it is hard to have that macro view when you’re micro affected.

And I think that’s what we become very overly attuned to is that this is affecting me now or someone I know now. And therefore I must have some kind of a feeling about this that’s bad.

Yeah. Really. Well said. We’re in exciting times, may you live in interesting times as the proverb sort of tongue-in-cheek says, right.

Yeah. And the thing that I really want more people to look at is how they can directly do things. And this is what I’d love to get your thought on. Jennifer, where can we, if we, as a people have, say, technology skills or something to share, where can we have a direct effect? Do you see the opportunity for us to empower people, to empower other people? I think this is the missing two sided market.

I mean, I have narrowed the list down to a few things. I think there are an endless number of things. It’s more of a mindset of do I take responsibility? What is my role in this problem? From there? There’s a lot of things that we can do. If you’re a hiring man, I’ll just throw it to you. If you are a hiring manager and I am a hiring manager now. And I’m finding myself saying, don’t be a hypocrite. Do what you think is the right thing to do.

Are you allowing yourself permission to look at novel skill sets when you’re looking for people? Because if we’re talking about a more I mean, ultimately, what we’re talking about is that we are going to live in a more digital world. And if we’re going to allow people an opportunity to survive and thrive in that world, but they don’t have a four year computer science degree, how are we going to address that? So looking at novel skill sets, allowing online certifications to be enough, looking at potential and broad capabilities rather than five years of Python and your previous job and a four year degree at this University, I think it’s hiring managers, the unsung hero of Middle America or middle management corporate America.

We really have a huge amount of influence on what the future of work looks like, even though you may not get any credit for it. So I think thinking about that, you have a very direct role to play in shaping the next generation of workers through your actions, and it will require risk, and it will require creativity, and it will require harder work. Diverse teams are harder to get to productivity as we know. So that’s something. I was always inspired. Microsoft was a fantastic company for many reasons, but also from a culture perspective, there was a culture of giving and giving back to communities.

I don’t know if it’s better or worse than any another company, but it was wonderful there. And I was so inspired that I had many hundreds of technical people on my team throughout my tenure there, and most of them if you ask them what they did in their free time, they were spending their Saturdays teaching robotics camps or coding skills and doing hackathons with kids and in their communities. And I think that is fantastic, especially when you get to underserved communities and communities of color or women or girls and STEM.

I think boys are just as important as girls, but wherever you find people who might need a little extra help getting yourself involved and I don’t think enough people are doing that. I would say also, I don’t see a lot of technologists in this policy conversation. We’re talking about getting really steeped into future of work, that would be something I’d rather see. And I guess my last point of advocacy would be for us to stop, to be very careful not to assume that technology is computing technology.

There are all sorts of solutions out there that are technology outside of our industry, and they are creating jobs. And if we can make sure that the people working on an offshore oil rig are adequately trained in the underlying technology concepts and the applications and use of their industry, that is a path forward in factories and event hospitality, health care, finance. There’s all sorts of non computing specific technology that the world needs to know how to use. And if we can give people those skills, we create a lift for everyone, so it doesn’t just have to be coding.

I think skills is such a great description of what we can empower like technology can be software, mechanical. It can be lots of different ways that we can create new ways to interact with systems. But systems isn’t always technology. There are people systems. There are very human systems that are out there that can be optimized, and I exploited to such. It sounds like a negative word, but exploited in, like, properly leveraged. So people in hospitality, even the simplest things. I used to be a shoe repair man, so I was a cobbler with a rare treat that you don’t get too many people that could say they’ve done that.

And I worked in a mall at the entrance to a subway and we had all this throughput. But the first thing I thought about was treat this like a system. How can I make sure that I can optimize the flow of people when it was rush hour, optimize the flow of shoes going through the system, right? Knowing how and teaching people who are not technologists, who I work with, how to think like a system. I taught them systems thinking. And I was at high school education.

I had no other than just my strange nerdish need to find optimization and everything. I got this, and I looked at the wall of stuff that we sold, and I started organizing. I’m like, what would entice somebody to come to the front of the store. And so I made the display differently. And I sort of built this journey through the little tiny store. And the funny thing was, six months later, we won a marketing award for a shoe repair by Cadillac Fairview, which is this big mall.

And they’re also pension fund as well. So the people that I worked with, what it taught them was that we’re amazing. We all have something we can do, something that we can reach for. And then the two guys that I worked with, went to get their own stores. And then one guy went independent, and he started his own shoe repair. That was entrepreneurship and even entrepreneurship with a paycheck just thinking about systems thinking and thinking about optimization and thinking of ways we can do that.

We created a better human experience for our customers and for each other, and no Comp-Sci degree required. It was pretty cool to see that we could pull that off.

I just literally love what you just said. That whole systems thinking approach, the idea of being able to discern a pattern out of chaos. If there was one higher level cognitive skill that I think in our education systems, we should be teaching, it’s that. And I’ve heard enough of these conversations that we’re all educators who agree, but I think they’re still in the minority. There’s this, I don’t know, this is going to be super geeky, so maybe not helpful. There’s this architect, a famous architect who I think was, I’m sure, a teacher at a University.

His name is Christopher Alexander, and he wrote this seminal book in architecture called The Timeless Way of Building. And I had a lead architect on my team at Microsoft who said, “You’ve got to read this book”, because what we don’t ever remember is that the underpinnings of anything we do when we’re designing a technology system are the very same underpinnings that architects use when they’re designing space or mechanical engineers are using when they’re designing roads and bridges. And they are all in their most fundamental elements, designed to reflect a human experience.

And it was a very big turning point for me to get clear on the fact that number one, technology is ultimately only ever an expression of our human experience, of the world around us. We just reflect ourselves in the things that we build, whether it’s a bridge or an application. But if you can start to cognitively, kind of grasp how to discern patterns, how to understand connections and relationships, then you’re much more equipped to understand the world, understand the problem you want to solve, understand where you fit in the world.

And I don’t think we do that enough. But that book, if you ever want to read a 400 page book on architecture. But he talked about how cities are built and how a house is built. A quick example. You intuitively know when the front door is in the right place of a house, we intuitively know this. We don’t need any training. And when it’s right, it’s when there is enough of a pathway to a front door. When it’s wrong, it’s where the front door is right on the street.

And the reason for that is that a house represents an intimate, personal space. And so the front door placement is a way of allowing us to slowly get closer to our space and allowing enough distance for people who are going to come into our space to do so in a slower and thoughtful space. You don’t want someone abruptly in your face in a first conversation, nor do you want them abruptly in your front door. And so it’s just a way of saying, oh, interesting. That’s why certain design elements in architecture makes sense to us.

It’s not because we know anything about architecture. It’s because we know everything about ourselves and technology is that way, too. But you can apply that thinking to anything. And I think then the world starts to get more understandable, like people get lost in the world of technology. We just feel like it’s passed us by or we don’t get it. And I’m here to say that you actually do get it, on some level. You actually totally understand it because it’s built on the same patterns that are echoed throughout your life.

And they’re human.

Yeah. This is the magical thing of seeing it. And actually, I always laugh at my favorite example is everyone smiles on it and will say, like bees when they create honeycombs, they’re perfectly hexagonal. Like, that’s amazing. It’s like bees know math. I’m like, I think you’ve got it backwards. These are patterns in nature that we’ve discovered, and we’ve built math to represent these things. And then we teach math as if that was the skill. But it’s actually the capturing of the pattern, not necessarily the learning of the task of measurement.

That was the zero to one thing that happened one day, the reason why the apple striking the head as being the sign of the start of gravity, whether real or not. As if the Apple knew what gravity was and just had to tell Isaac Newton, by the way, here you go, here’s an idea. It was a variety of things that suddenly was like, aha, but it was the recognition over years of looking for a pattern and then seeing it. And it can be very small things.

That’s why, even like, said servers in restaurants. A great friend of mine, he’s been working as a server, and he goes now like he has a SWAT team of servers. And they go into new restaurants like Gordon Ramsay’s little TV show where they like, ‘You’re doing it all wrong. And here’s how you do it’. And they teach people how to optimize the flow for customer experience, including the chefs and all these interactions. And he says, what do I teach people? He says, “I hand them this as the most bizarre book that you wouldn’t think you’d hand to a restauranteur.

But I give them The Goal by Eli Goldratt, which, if we are in technology, is the foundation of the Phoenix Project, which is the entire DevOps movement, is based out of this idea of how do we optimize flow. And Goldratt wrote this book, in I don’t even know, it was like the 60s or 70s. Talking about the manufacturing industry and lean manufacturing led to lean startups and lean development. And just like, we think that the bees know math, no. Here we are. So here’s somebody teaching a serving crew at a restaurant.

And then when it comes to taking on technology, those group of people, they start to look at this system now and go, you know, it’d be better is if this menu was done this way and they are now driving the experience for the developers and for the restauranteur and saying, like, ‘It’d be better if we put the system here’. And they are invested in their own outcome. But then, as a peer group, it raises us all to be able to just ask a question, don’t just come in and do it.

That’s the beauty. It’s like when your kids say, why, for the first time, you’re like, oh, that’s cute. And then it becomes very uncute because they ask why about everything.

So true.

But then you realize it’s beautiful because they are genuinely questioning it. And you’re like, I’m so happy you’re doing that.

It’s so good. I mean, we could just get super nerdy here, but it is a reminder that through our evolution, we are born optimized to understand the world at a very intuitive level, how that happens. Neurologists can have the nature nurture conversation that happens all the time in the AI spaces, you know, like, does the system have to start from scratch, or can it be built in with a few things to give it a head start? Because people are. Babies are born with the way we function neurologically is optimized to be a reflection of the world already around us.

And that’s why things make sense to people all the time. But it’s important because it is a mindset shift of, I start from a place if I can. The world is not foreign to me. Any manifestation of the world, technological or otherwise is not on some level foreign to me. It is simply an expression of the laws that I was born that were internalized in me the moment I was born, that we are optimized for the world.

And it’s just a matter of patience and understanding and study and observation that I can become more efficient and efficacious in that world that I start from a place that I can.

I’m curious, who are the people that you look to as more recent inspiration? Like we can always look to the philosophers of old and sort of our early teachers. But who do you see that you find is reflecting a new existence and doing it well, nowadays?

I think I look at people who are talking about this. So there’s a gentleman, Erik Brynjolfsson, who’s now at Stanford, and now I’m going to forget the name Stanford Digital, something other. He was at MIT, and he is an economist and technologist who talks about future work. And so much of what I understand is from his work. So I think everyone should follow him. But then there are the innovators, like the Elon Musk’s of the world. I know he’s overused, but the reality is there’s this charm of not getting so excited about the fact that he’s solving a big problem that I think is exactly that mindset of you have to get yourself into a space where you feel like if you just thought about things, use that kind of root cause analysis and ask a bunch of questions about why things work the way they are and uncover your assumptions about things that you actually can get to a very rich understanding of the world around you.

And from there understand how you can affect it. So I don’t follow a lot of people on a daily, weekly basis. But those are two. For the world itself, Ian Bremmer, I’m a huge Ian Bremmer fan. Nobody knows who is. He runs a group called the Eurasia Group. He talks about world and world politics, and I think he applies that kind of thinking to the realm of politics and policy and global affairs. And so I think maybe it’s more about people who I think use that mindset and apply it to whatever it is that they do that I’m inspired by.

I pulled over a book just because I literally wrote this down because I was listening to Antifragile. It’s Nassim Nicholas Taleb. Famous for Black Swan and a lot of things. And the one quote that jumped out of me says, to be a successful philosopher King, it’s better to start as a King and then become a philosopher. I find that it’s the practitioners that are truly creating the next philosophical discussions because before it was always from academia, then teaching the world how it’s supposed to work.

But I find this is an opportunity, we can turn it on its head. And much like you talked about Elon Musk. Right. First principles thinking even in the smallest format and things we do of like, why is it that we do this thing this particular way when you see people that are doing stuff in practice and they’re saying, I don’t want to go to an office, they’re saying I can become a gig worker. I can become my own landscaper. I can start my own shoe repair.

I can start a startup using no code and low code just because I’ve got a problem to solve. But it’s very much often people with lived experience that then just can take this and almost question the philosophers of old and say, I think we can do something here. I think where we’re going to see ten years from now, a lot of stuff going on that’s already happening, but it won’t be realized in public effectively until the next wave of startups kind of make it to whatever status is where we look for unicorns, or just the fact that longevity. We will see more longevity in small businesses, and people will see those new statistics.

And that’s the future of all of us. Actually, this is a fun part when you’re looking at the future of things, and we’ve clearly gone through very literally a Black Swan event with what’s gone through with the pandemic and what’s still continuing with the pandemic, of course. But are the things that you looked at five years ago that either are holding true or maybe even were accelerated because of the most recent 18 months that we’ve gone through.

I have to just take a second to go back to five years ago. So I’m literally like, wait, what year was it five years ago, 2017. Where was I then? I think that my understanding of how problems need to get solved on a small level kind of back at the very beginning of this conversation. That the boundaries of a problem matter that actually has a relationship to this whole democratization distribution of technology knowledge, because when you let everyone solve their own small problem, I think there’s a bigger aggregate effect than when you assume that only a few organizations or there’s a real centralization of problem solving capability and all the money and power and intention flows to that.

And I was seeing that in the context of a lot of the digital transformation projects that we were running, and if you go work for the big Fortune 50 at some level, you’ve got to get C-level people to sign up for projects that are extremely so expensive that the board has to approve. And they have very dubious ROI because it’s an innovation project. How do you know it? It’s an experiment. So it’s not that you don’t see it at that level, but they only work when they were inspired by people who are actually out in the field, whatever the field is in, whatever industry trying to get very specific about a problem.

And that was when I realized, oh, my gosh. The democratization of skills is important because you need to empower everyone to solve their small problem, and that’s going to create a shift in power. Right knowledge and efficacy being power if you let people solve problems and you give them technology, then they’ll do it. And of course, remember, I have a son who can Twitch and all that sort of stuff has been in my house for a while. So I’ve kind of seen that, too. So I’d say that would be the pattern that has stayed true, and I think it’s going to continue to shift.

I didn’t know it was going to look quite like this, though.

Having kids. I’ve got four kids and I’ve got 20, 18 and 5 and 2. So I’ve got quite a range of things that I’ve seen, and I sort of laugh now, people that have young kids, especially that we all know about sort of the YouTubers and these Blippi and Ryan’s Toy review. And there’s all these very popular things. And there’s one kid, who you look at his videos five years ago, and it was just basically filmed on an iPhone, not even a good iPhone, but an iPhone seven or six, whatever it was at the time.

And this year, he was in Fortune reporting 26 and a half million dollars in revenue.


He’s eleven years old. There is very unicorn-like capabilities in exploiting these. Finding the pattern, exploiting the system that allows you access to uncover and use that pattern. And that’s kind of cool. The economy is so different now, but I think I’m like you. I like the democratization, and I think the last 18 months, though, not anybody in the world wouldn’t trade away. What we’ve had to go through as a society. What we have to do is find the best of what we did. And I think the great resignation startups moving to everybody’s mindset, people realizing you can just do things on the Internet and you can begin to generate revenue.

It’s a new economy, it’s a new world. The one thing we didn’t get a chance to talk to, but it’s still early on. So I’m going to have you back because I want to get your first few months of experience. So I have to say Congratulations in advance that as this is out and people are listening. You are the CEO of a new company and you’ve been involved, so, in the last couple of minutes here and I apologize. I don’t want to box you in, but just as a bit of a teaser to what’s coming up next for you, Jennifer.

Well, we’re going to go through a big rebranding renaming event, so I’m hesitant to talk about too many of the details here, but it’s a company that’s in this future workspace from an industry taxonomy perspective. You put us in the HR tech space, but I’m concerned about workers that are not in the tech industry. I’m concerned about workers who are not on LinkedIn, and I’m interested in how we can within the existing ecosystem of how people find work, which is through staffing, agencies and employers. How can we give people access to a proactive profile building capability that allows them to find work to go out and find work?

They advertise to agencies and employers based on the profile they build for themselves. So I got the advanced certification. I was making $18 an hour. My profile has changed. I have really great five star ratings from my last two employers. I’ve got a few verified skills, and now I think I could earn at least $23 an hour. How do you do that? What’s the platform in the marketplace that you build to do that? So the company is already kind of in that space and a little bit narrower because product market fit is important.

But that’s the aspiration of the company. And ultimately, I think it’s providing that LinkedIn active profile building capability to the rest of America, and then hopefully the rest of the world.

That’s amazing. And Congratulations on the big move. And I’m excited about the future there, inevitably, with you as part of the leadership team and then heading it up. They’ve got success ahead for them. And so it’ll be exciting to watch. So it’d be great to be able to see post rebrand. I know that’s always an interesting challenge for any organization, so it’s always fun that we get to be secretively leading up to it. But this will be, actually the said timing, as it were, this will probably be pretty close to when you go live.

So I’m excited about that. Jennifer, if anybody wants to reach you, of course, well, I have links to your website. And where can folks find you if they want to get connected?

Well, I think by the time this publishes, I’ll have a whole bunch of new contact information, but I am a big fan of LinkedIn. I use it and I’m on it all the time, and people reach out to me all the time there, and I always reply, so that would be probably the single best way to find me.

Excellent. You’re better human than I am. I’m the worst, because the thing I get the most at these days is people trying to sell me explainer videos on LinkedIn is particularly good for prospecting. And for whatever reason, once you have a very public voice, people see you as a great prospecting target for a lot of things.

Thank you. But I’m so grateful for that platform, so I really take it seriously. I do try to kind of be somewhat active. I post all my podcasts there. Not that everyone wants to listen to me. And I just try to be useful on the platform. And I try to be grateful for the people who reach out there because you never know any. Of course, there’s lots of sales pitches, but that’s okay.

And like you said, I’m really mindful of the effect that it can have. And really, the last job that I took, it was kind of funny. After I was at the company about three months, the human resources team, they phoned me up and they said, hey, Eric, we realized that we don’t have a resume of you. We’re supposed to have one on file. So can you do us a favor? Can you write up and send me a resume? Because that is the future of work for a lot of people that there is no more filing the CV and sending with a cover letter.

It was, somebody sort of found me on LinkedIn and they followed my blog and we met an event and I interviewed with a bunch of people. And the offer comes it was a very different world. But yet the old classic practices like, we’re supposed to have a resume on file somewhere just to say that we looked at it, which is crazy.

I know it’s kind of crazy. And when you get into the lower end of the wage scale, resumes are just not even necessary because you get people early in career. So I will say one of the features that we have is this video capability. So kind of like TikTok where I can film myself answering questions and in three minutes, a recruiter or a hiring manager can get a very good sense of. Can I show up? Can I talk? What have I done? What’s the look and feel?

What’s my authenticity? Am I real? I’m not even my actual person. So I think that’s the future, especially for a lot of those jobs where you just need to make sure, I’m going to be serving people. You need to make sure I can serve people.

Yeah, that’s right. I am very excited to dig in on this one. So there you go. Once the new name is unveiled, we can have you back on. We can do a deep dive into what you and the team are doing.

I would love that. Thank you. Such a fun conversation.

Great. Thank you very much.

Alright. Thanks, Eric.