Evolving Selves, Evolving Work

Rachel Cossar: Welcome to another episode in conversations in the future of work. I am your host, Rachel Kosser, and I’m really excited to dive into future of work recruiting and what we think is coming on down the pipeline in the next five years. So without further ado, Anne Marie Penny, welcome to the show. Hello. Glad to be here. I’d love to hear, you know, share with our audience a little bit about yourself, your background, what you’re most excited about these days. Absolutely.

Annemarie Penny: So I’m a three time founder. Started out KPMG Finance. Came to California as a teenager with $200, and, really, I like to typify my career gratefully as the combination of consistent hard work and authentic relationships. Because at the end of the day, this is about people and always will be. So I launched the first recruiting firm in Los Angeles to focus on dot coms back in the nighies before anybody knew what that was. And so, it’s been a a wonderful life building hundreds of start ups, VC backed, self funded, everything in between, many of it acquired by, you know, very, very leading brands, particularly in the technology industry. And at this point, as CEO of DreamMore, we are very much embracing the future of work with the perspective that the tools and the technology have changed dramatically over the last thirty or forty years. But the people, we’re still humans, and we’re gonna run everything through that lens. Yeah. Awesome. I love that perspective.

Rachel Cossar: I think it’s so easy to get distracted by the noise of technology and to think that things have changed so fundamentally. And in some ways, they have, but in many ways, they haven’t. So, you’ve just mentioned so many different paths in your past. Right? So I’d love to know, like, how do you feel I I find, like, you know, transition and evolution is a very fascinating topic to me. And so how how do the various threads of your life kind of intersect and weave into this new world of work? Absolutely.

Annemarie Penny: And, you know, this is the thing about the future, and I like to point out to people, you You know, we’re in the future right now. Every second that goes by, you know, this begins becomes the future. And so, coming out of KPMG finance, as a very young person, I was trained to always look five years out and then back into where are we today. And you can equally say, okay. Well, we don’t know what the future holds, but we can certainly use some analysis and data to predict. And so part of this year in particular, embracing the future of work as a concept and knowing that in some circles, that just means, you know, HR tech and some tools that are implemented. In other circles, that literally means things that used to be so crazy, like driverless cars and quantum computing. This is also the future of work. And, frankly, the future of work is more than just technology. It’s really looking at the social construct. So this was very much part of the journey this year was equally going, let me stop dwelling on what’s right in front of me and being reactive and look at five years out, where do I think this is heading and then back into it. Look back in history and go, okay. Well, regardless of these things that feel very new and different today, there are all of those common things that don’t change, which is our brains are basically formed the same as they were thousands of years ago. And so we can look at historical patterns and even recognize that in its time, you know, the steam engine was technology. The wheel was technology. Fire was technology. And so that can actually inform beyond just, oh gosh. AI is gonna take our jobs, and I don’t know what to do about that, and look at it more from, alright. What did we do as people before and how to react to things, and then how do we survive, and how did we ultimately come together again for that survival. And the last point on this as it relates to the future of work, everybody has a different mindset around this, and there’s a lot of fear mongering right now that really makes me sad because we don’t operate well as people when we’re operating from a state of fear. Yeah. And so very much, DreamMore’s approach to this, you know, DreamMore has one m in the name, and Amore is the Easter egg that’s buried in our name because that is love and that is a pure state. What if we looked at everybody not as a competitor or as a threat? What if we looked at each other as a possible friend and a possible ally? How different would our world be? How different would our business world be if we view everyone through that lens? I love that.

Rachel Cossar: I think it’s a really nice reminder, especially for founders who are in such a hyper competitive mode. And, of course, I understand being a founder myself. Like, it feels like a very scarce world in many ways, but it’s almost like to your point of instead of looking at people as enemies, we have to take down, you know, what what would it be like to think that you’re or to feel like you’re really in a world of abundance. That’s been really helpful, I think, just in the way that we approach other people in our space too. You know? Like, it’s it’s it’s great to have more activity in your space. Like, yes, it’s competition, but there’s a certain amount of competition that is almost necessary to really mark whether you’re in a a legitimate space or not.

Annemarie Penny: You know, if you have an idea that is so original that nobody else has anything near that idea, that in the investment community, that’s a bad sign. Right? Right? Yeah. It’s really interesting. And I do come from you know, besides the, you know, KPMG experience, you know, I’ve spent thirty years in executive recruiting, and there’s tens of thousands hundreds of thousands of recruiters in the world, and they all specialize in slightly different things. And so I think also from a very early age, I recognized, oh, wow. Yeah. Yeah. Of course. You know, this is business, and companies are made of people no matter what they do and what they sell. Yeah. And, of course, there’s gonna be hundreds of thousands of recruiters all trying to solve this human capital problem in different ways. Yeah. And you can look at somebody that specializes in my same specialty as a threat because there’s more work than we can do even in tough times. Yep. And so, frankly, with excellent mentorship in an early stage, that’s also where I’m very grateful. She really imbued in me this concept that anyone else in our profession that is elevating, treating people with kindness and respect and really doing their job well, that elevates our whole function. And for all the computer haters out there, I get it. Sometimes it’s been very dehumanizing, especially these last few years, that anybody who still has a heart and a soul and works hard to help each other hey. You’re my people. Yeah.

Rachel Cossar: So you’ve mentioned recruiting a number of times, and and I’d like to just, better understand some of the challenges that like, having observed this space over so many years, what are some of the challenges that you see in the recruiting space at the moment? Massive. Yeah.

Annemarie Penny: So, you know, I I like to describe you know, I’m one of the OGs of technology. Right? Having started out in the .com era, which is not when technology started, but for a lot of us, that’s when it really became dream. And so all of these tools and systems and you know, even when I was in finance, I started in finance when Microsoft Excel was a brand new product. And so from being a teenager, I have been hearing the same thing. Oh, wow. This is gonna 10 x your productivity. This is gonna give you all your time back. And and Mhmm. Has it really though? Because what has ended up happening and this is a huge mindset and cultural issue. It is not the technology’s fault that we keep creating and believing that all of these extra tools and systems are making our lives automatically better. So that is a big challenge that recruiters being in the human capital business, you know, back in the back in the nineties, you know, I could keep a lot of this information in my head. And we met everybody in person, and you’d have a nice forty five minute, you know, let me get to know you. And you send three resumes to the client who did not expect a 100 resumes, and they didn’t expect it tomorrow. And so this is where we’ve had this 10 x thing and 100 x thing, and everybody needs to be a unicorn in this. It it just doesn’t scale. And so I think if we go back to what is really happening and these concepts that at the end of the day, we’re still people and our brains have not changed that much, and that is a good thing. Let us embrace that because we’ve lost in a lot of ways staring at our screens all day, trying to manage our inboxes. That is not your purpose in life to respond to everything immediately. Right. Right.

Rachel Cossar: And it it’s just led to a lot of burnout.

Annemarie Penny: So this informs everything that we are building related to the future of work where let’s just recognizing that hiring is is broken right now. Mhmm. And so layering more tools on top of tools and doing keyword matching and and trying to, you know, play a numbers game, that that’s not actually how recruiting works. And and it’s creating we gotta go the other way. That’s all I’ll say. Because I the the the burnout in all directions makes me really sad because this is a people business. And I think we’re all so overwhelmed and stressed on certain levels that we just are forgetting how to beat people. Yeah. Right. Yeah.

Rachel Cossar: It’s interesting your point about, like, technology promising all these things, but then whether or not those time savings are actually happening and we’re just then filling, right, it’s like gas in a room. If there is more time, it just gets filled with more tasks and more emails and more urgency and whatever. But it is a it is a problem. It’s like, for example, these, like, meeting bots where it’s like, okay. Great. You can’t go to that meeting? No problem. Send your bot. And it’s like, okay. Great. So now we’re like, we already had before the pandemic, there were already too many meetings. People were not being efficient with their time. There are already too many meetings. And now that we have these bots, we can actually instead of, like, taking a step back and thinking about our time and our resources and how we’re spending those things, we’re like, it actually sure. Have a meeting. Have a meeting of bots. Let the bots just talk. You know? And you’re like, what are we talking about? You know? You know, it feels dystopian.

Annemarie Penny: There are so many things that we don’t know are happening. So I just I was imagining that, you know, there’s there’s all these these biomes in in my digestive tract that are doing a bunch of things that I’m not even aware of, and that doesn’t bother me. But I think somewhere in all of the fear mongering and, you know, what we’re seeing and getting freaked out is like, yeah. It is freaky because it’s different and it’s strange and we don’t understand it. But on the other hand, there is this opportunity to go, we shouldn’t even be bothered with any of this stuff. Like, why am I trying to manually do all of these things on a computer screen where, you know, how many of us are, you know, like our our bodies were not formed for this kind of interface. Yeah. And so and our mental health is suffering. And and so, like, it is just an opportunity. This has been a lot of the rhetoric here lately is just to encourage people. First of all, take some deep breaths. The the it’s free, and it it is amazing what it will do for you. And then question things. You know, use some critical thinking and just we used to use this term a lot in recruiting to help people make career decisions, which can be very challenging when you’re managing. Do I stay or do I go? And which salary offer? And what about my spouse? And all that. So what if today is opposite day? Just take everything that you go. I have to do this, and this is how things are. And just literally flip it the other way. And even if it’s silly, like, what if today I walked on my feet instead of my hands? It just, like, pick up these patterns of thinking. Mhmm. You know, it’s it’s fun. I know we’re talking about the recruiting space, but it very profoundly impacts the recruiting space because we keep layering all of this energy and not actually pulling way back and getting a perspective. What are we trying to do here? Why is it business? Why is it hiring? Why is it work? What’s our purpose? Like, these are fundamental questions that not only are they not a waste of time, but they are the questions that need to be asked. Not like, oh god. Do I need to take a CHAT GPT certificate to better qualify for the next job? It’s meaningless. Right. Right.

Rachel Cossar: It’s it’s hard to not be distracted by the noise. Right? So how are you like, there’s a there’s just so much noise going on now. Right? And people’s attention is being pulled in so many different directions. So how do you address some of these challenges in your space, either through your own, like, LinkedIn very impressive LinkedIn presence? You know, I know you’re working on a number of interesting projects, but what would you like to share in that regard?

Annemarie Penny: So the future of work is really what we make it. But I I went on a deep dive exploration this year, and I said, okay. I’m having a a visceral response to all of these tools on top of tools. And having the perspective of someone who’s been in the industry for thirty plus years where even from back in the day, we knew that a lot of what’s going on with ecommerce and social gaming and social media and all these things. It’s like, it was just a data grab. A lot of gamified. It was a lot of things that were tapping into how our brains normally work to be able to, frankly, you know, build empires in these organizations. Mhmm. And now we’re all, you know, bringing in from past eras. You know, we still get guilty if we’re, you know, not working Monday through Friday. Right? You know? So we we have these past patterns that we’re still bringing into this era. And now we do have as much as everybody’s talking about AI and we make jokes, but if it depends on the AI, you get a flower. And so it’s a big distraction, but it is also legitimately a force multiplier for everything that’s going on with. It. That’s a big distraction. So if we keep taking the ways that we have looked at recruiting in the last thirty years Mhmm. And, hey, I have a resume, and I have a job description, and I need to match that, and then I need to, you know, have an interview. You know, all of that has worked up to a point, but, you know, look look further back and go, you know, even forty or fifty years ago, that wasn’t how it worked. And so we can’t keep just piling on and piling on and being like, well, this is how things are. Right. And so when we’re looking to solve certain problems I looked around and I saw so many tools on top of tools is my phrasing for it. It’s like, yes. We need to solve mundane tasks. But a very dear friend of mine, I remember I was all excited. I I hate my inbox. And so I I got a tool that was gonna organize it. Right? And he just looked at me, brilliant, and said, well, why aren’t you solving the problem at the source? Why do you have so many emails? Yep. Yeah. You so, like, even the smart kids in the room sometimes were in the stimulus response reacting mode going, oh, shoot. So here’s the thing. In terms of where the futures of work is really headed, and we are looking to build something that is a pathway because the reality five years from now, work looks very different. And it is already happening today, and that is why it informs liquid workforce. You know, for example, the way that currency is happening, so how do people get paid, is is changing. What does even wealth look like if, you know, you you don’t have all your time and you’re sitting on a pile of money, but you’re sitting at all, you know, for taxes and insurance? Like, you know, these are things that that need to fundamentally change, and they are, things that we’re addressing with our platform. Simply put, there is an opportunity for the technology. AI is not software. It is a dynamic learning and semantics, and there’s a lot of things that are coming out right now that are exciting where a lot of the data scientists and the linguists and the communicators are actually you know, we we’ve got a good competitive edge compared to a lot of technicians and software that is a very different type of technology. And you don’t actually have to be technical to understand this. So that is the encouragement for everyone out there. Right. You the playing field is level, and this is your opportunity.

Rachel Cossar: Yep.

Annemarie Penny: So with our platform, we are recognizing that interviewing and hiring and resumes and all of these things that we’ve been using for a few decades is gonna fundamentally change. Yep. And to be able to take advantage of the way this technology learns so that we can learn together and create upskilling that is bespoke and really understands you and knows you Mhmm. In a safe environment where you own your own data. Yep. That’s what we’re doing. Yeah. Yeah. No.

Rachel Cossar: I mean, that’s really powerful stuff, and it’s, I love your comment about, you know, you don’t have to be, like, a technical whiz to leverage these tools. They’ve really blown the the way open for people to have a vision and then leverage the tools to bring that about. Right? And that’s, a real it’s a really exciting time. What are you excited about for the next, like, five years? You know, I am excited.

Annemarie Penny: This is my red pill or blue pill conversation. So things can be true at the same time because we all have different perspectives and, you know, reality is mindset in many ways. So it is true that there is a massive power grab right now with industry elites in a sector that people like me have helped create. And thirty or forty years ago, that was not our intention. We’re bunch of nerds and creative founder types that just wanted to solve the problems. But here we are fast forward in an era of unicorns and and massive data centers. So that is a is a legitimate concern. Everybody needs to understand what a digital twin is and understand that the way technology is changing is as different as in the early nineties. We didn’t have text and email and an Internet, And look at us now and all the things we’re doing with getting this experience today. Right. So everyone needs to understand that if you don’t take the power and help define this version of who you are. It will be determined for you, and that’s extremely fair. The question was what I’m excited about Yeah. What I’m excited about is that this is also a massive opportunity for the playing field to be leveled. Right. We’re in a world that hasn’t existed in this way before. Right. And there are many, many of, my female friends, my my gender spectrum, black, brown, underserved communities you have an opportunity to get your voice heard Yeah. In a way that hasn’t always existed. Mhmm. And the pathway is to tap into what makes you a person because nobody else can be who you are. And this natural curiosity, this continuous learning, this enthusiasm, these things that we have as little kids, and it gets squished out of us because we have to be grown. That’s the opportunity, and I’m super excited about this. Right. I love that.

Rachel Cossar: I feel that’s a really important reframing. And I heard, I think it’s actually my husband said this the other day. He was like, people who there will be people who rely almost exclusively on ChatGPT or or GenAI to develop their thoughts and their sense of the of themselves. And there’s a risk in that because people will be getting similar information. Right? It’s like if have perpetual memory. Right.

Annemarie Penny: There’s a massive environmental concern of the LMs. It it has short term memory Yeah. And pattern matching.

Rachel Cossar: So it doesn’t know you, like, you think it does. Right. Exactly. And so people who learn to use these tools for their strengths but continue to develop themselves going back to what we started with in this conversation as humans first, Like, that, like, that is the way. Right? And so it’s really interesting to keep that in mind, and I don’t think it can be said enough. 100%. You know, I have a very dear friend.

Annemarie Penny: You know, I’m hearing that in parts of music and all of these other things that make us a people. This person, was very ill in their twenties, and they’re now in their fifties, but they’ve been living on borrowed time ever since. And their interpretation of that near death experience that continues was I need to be the most talented and productive artist I can be. I’m gonna lean into that because I have this opportunity, and it’s limited, and that’s my gift back to the world. And it just it struck me on such a level to hear his story and and collect his art and be part of this. And we don’t all have to be that intense or dramatic. But I think on any level, if every human being woke up and was like, you know, I wanna be the best Rachel that I can do today. Mhmm. And do it again tomorrow and do it again the next day. Nobody is who you are, and I don’t always know that we embrace that to the level that that that’s awesome and has so much possibility. Yeah. Yeah. I I mean, that’s such a strong message.

Rachel Cossar: You know, Anne Marie, I wanna thank you so much for coming on the show and sharing your perspective of of experience and then also just, like, really being deeply involved in some of these new and emerging technologies and AI. Anything else that you would like to share with our audience? Where can they find you? Where can they interact with you? Absolutely.

Annemarie Penny: Our website is either dreammoreai.com or dreammore.io, and definitely all over LinkedIn and other socials. If you don’t find me as Ann Marie Penning, usually, our handle on TikTok, Insta, etcetera, etcetera is dream more dreams. Glad to help everybody. We wanna make the world a better place, and that is through being the best humans we can do. Awesome. Great. Awesome.

Rachel Cossar: Well, thank you so much for your time and for sharing your perspective. And as always, thanks to our audience. We’ll see you next time.