Inside Upwork: Lauren Dycus on AI and Market Differentiation

Lauren Dycus, Director of Product Management at Upwork, details her role and the company's mission. She focuses on work management, which streamlines processes from user onboarding to contract finalization. Upwork, the world's largest work marketplace, supports freelancers with specialized skills, enabling personal and company growth. Dycus emphasizes Upwork's commitment to equity between clients and freelancers, supported by a culture valuing empowerment and fair opportunities. She highlights a new bonus prompt feature designed to enhance freelancer-client relationships and foster long-term partnerships. Additionally, Dycus discusses Upwork's ethical AI approach, stressing human-in-the-loop protocols and data protection to ensure fair treatment for all users.

Lauren Dycus Notable Quotes:
🌐 "Upwork is the world's largest work marketplace, where freelancers can scale companies while growing their own."
💼 "Work management is the heart of Upwork, streamlining everything from onboarding to finalizing contracts."
🤝 "We're dedicated to making the freelancer-client relationship more equitable, ensuring both sides have agency in their work together."
🚀 "Our new bonus feature is designed to strengthen long-term partnerships between freelancers and clients, moving beyond transactional interactions."
📊 "Adopting AI responsibly, we're focused on maintaining human oversight and ensuring data privacy to protect our users' interests."

Resources Mentioned:
Upwork’s AI Principles
Upwork Bonuses
Financial Feminist by Tori Dunlap

About Lauren:
Lauren Dycus has spent the last 15 years shipping features in software and AI product development at Amazon, AWS, DISCO, LTK, Microsoft, Upwork, and more. Focused on building with agile methodologies and user research, she develops teams and products that solve problems while growing global businesses. Dedicated to mentorship and diversity, Lauren's leadership expertise spans games, ecommerce, robotics, legal tech, and cloud computing, to prioritize safe, collaborative environments for product innovation.

Connect with Lauren:

Chapters

• 0:00 Introduction and Overview
• 1:58 Work Management at Upwork
• 2:36 Upwork's Differentiation in the Market
• 4:58 AI Policy and Responsible Adoption
• 8:23 Bonus Structures and Freelancer Equity
• 9:10 Data-Driven Decision Making
• 15:51 The Future of AI in Product Management
• 22:17 Surprises and Learnings in the Field
• 23:31 Career Path and Job Selection
• 28:20 Hiring and Team Composition
• 39:01 Advice for Getting into the Field
• 44:12 Long-Term Perspective and Business Growth

Transcript

0:00

Hi, my name is Joan Palmiter Bajorek. I'm on a mission to decrease fluffy hype and talk about the people actually building in AI. Anyone can build in AI, including you. Whether you're terrified or excited, there's been no better time than today to dive in. Now is the time to be curious and future-proof your career, and ultimately, your income. This podcast isn't about white dudes patting themselves on the back. This is about you and me. and all the paths into cool projects around the world. So what's next on your AI roadmap? Let's figure it out together. You ready? This is Your AI Roadmap, the podcast. Hey folks, this is Joan dropping in to say a little intro about this episode with me and Lauren. I'm so excited for you to hear this one. I know quite a bit about Upwork and kind of this product. And I think it's so cool to hear from someone working on it about how she thinks about freelancer and client equity and really thinking about this relationship that they build on this platform. I love hearing about how they have AI policies internally and the company is really thinking about upskilling their people, which is so cool. And to talk about that, literally more companies need to be doing this. So props to Upwork. I was impressed. And also I really love how Lauren thinks about data -driven product design of different features they roll out, how they name the different parts of the product. It's such a cool episode. I think you're gonna love it. Let's dive in. Hi, my name is Lauren Dycus... Oh, go ahead. Please introduce yourself. Hi, I'm Lauren Dycus. I'm the Director of Product Management at Upwork. It's nice to meet you. Nice to meet you too. Thank you so much for making the time. I'm so excited to learn from you today. Okay, Lauren, so what are you working on? So for the last 11 months, I've been at Upwork working on what's called work management, which is the simple way to describe it is the heart of Upwork where the work gets done. So we work with partner teams that kind of bring users onto Upwork. And then once they've decided we want to work together, they come into the area of the product that I own related to contract terms, executing that work, and then finalizing the work and capturing kind of the outcome of the contract. pulses blood to a lot of the other teams where they get the data that they need to be able to deliver their experiences. Oh, that's so awesome. Well and for those of us who, or for people who are listeners who don't know what Upwork is or are not power users, what is Upwork? How do you all differentiate yourselves in the market? Upwork is what we call the world's largest work marketplace. We have a freelance and hybrid work platform for anyone that is really having a specialized skill. Think about it as more of the white collar behind a computer task that you can help somebody else scale their company while you are growing your own. So we really help the freelancers kind of create opportunities to build the world that they want to work in, you know. Maybe they want to join a full-time team, but it is a job marketplace at its core. That's awesome. Well and I think what's so, I was checking out this morning trying to see new, new features and things for preparing for this and it's got this awesome like find talent, get hired. Like this two sided marketplace I find, or at least on my side of it, looks more equitable or there's some kind of like agency that both sides have in getting to those contract places that you're talking about. Yeah, that's one of our biggest missions is the equitability of both parties. Especially if you go listen to our CEO, Hayden Brown, she always talks about just the balance between the two. And I think the culture of Upwork also leads with that, and like our legal team won an award for developing an AI policy within like a couple of months of chat GPT going public. And so it's one of the places where we very much want to empower our users and give them equitable footing to say, And that's kind of where I come in as a contract terms, right? We just released a feature actually at the end of the year that a woman on my team led Jackie related to prompting for bonuses. So clients, and we learned this through user research, that clients often use a bonus to like care it for a better relationship with either party. And it's something that's not seen as a tip. You know, these are professionals, these are people that like want to work together long-term. And it's something that gives freelancers more opportunity to earn. It gives them something to go above and beyond for to develop that partnership with these clients. And we actually see some clients are also freelancers, which is really wonderful as a product leader to get feedback from them. But it does as a two-sided marketplace, it has to be fair. They know both sides. And that's really our position is trying to make it much more equitable. And I have team members on my team that we hire engineers from Upwork. that are in Ukraine and Palestine. And it's really wonderful to feel like you can help people that are in a part of the world that they wanna work, they wanna contribute, and if they didn't have the internet to get there, they wouldn't be able to connect and keep working. And so I love that you said that though, that is very much the position of Upwork is a freelancer equitability. Yeah, well, just on the website, it looked like you could be here for either thing, and both are appropriate. You know what I mean? It wasn't like a funnel to the wrong place, like back door, front door. It was really interesting. Well and I'd love, you've mentioned so many different cool projects. If I could just, to this extent, you can talk about the AI policy. And I think a lot of companies are either scrambling or not scrambling, and always trying to figure out their own policies and how they think about AI and adopting it. Would you mind sharing a little bit more about AI policy stuff? And I was not part of that team. That was our legal team that I'm just, you know, very lucky to get to work alongside. But they came out with an AI policy that gave instructions to the company. You know, as a product leader, it's very important for us about the decisions that we make of what we adopt, but also for everyone in the company who could be using generative AI tools like chat GPT to be aware of the policy. And they quickly followed that up with trainings across. And it was led by our... Chief Information Security Officer Paul Black and his team that kind of rolled out very comprehensive and approachable education that I still went to and just wanted to learn about how they're presenting it. But specifically around the AI policy for us was around risk because we are in a job market, right? We're a global job market and there are very wonderful protections for workers around the world. And as Upwork, we have a fine box that we need to work within where... only the client and the freelancer are making calls about who's doing the work and what that entails. And we just create the opportunity for that negotiation to happen. And so, you know, making sure if we adopt Gen.AI that there's still a human in the loop protocol, right? Like someone else needs to come in there and say, yep, I agree with this and I'm moving forward with it. Where we wouldn't have full AI that's making decisions without a human and that's kind of core to our policy as well as, you know, information sharing in a corporate company where you the same way you wouldn't want to post something on Craigslist. You know, you don't want to put something in an open shared chat GPT or gen AI model, even if it's enterprise, because there might be private information that we only want within our company. And so they had to educate people about the basics around how a model training works and how, if we give our information out there, it could expose us to risk. And we have just a wonderful legal team at Upwork that is very informed and educated on technology. technology policies and they partner even with our product teams on Should we adopt JNI and which partners should we work with? Because of how those partners store their data and how they model their data and we protect our user data Very heavily, right? It means a lot to us so that policy was rolled out and then the trainings were rolled out along with it and we have guidance around tools we can use as while we're also experimenting with the tools that help us do better as individuals, but The policy was very much to help us as employees do our work better rather than, you know, enforce, uh, you know, repercussions for any wrongdoing in any way. That makes so much sense. I think all companies would be wise to do such things. I think we hear of the worst examples of people putting source code from Samsung into an LLM, which just like, you would think that's relatively obvious or I've heard the example of like, you wouldn't put source code into an email and just send it off, but somehow into LLMs, there's this, I don't know, trust going on, but everyone needs to be upskilling and defining protocols, I believe that they're companies. when you get to work on a really cool feature or at least your bonus or like as I'm going back out to restaurants and things they always show like different tip options like which button do you want to press which there's all these other implications to that thought process. Can you tell us more about kind of like bonus structures like I guess it's at the end of a contract when people are paying up? and of a contract and it's something that we are looking for freelancer equity tools and we had one kind of contract path that had this opportunity and the woman on my team Jackie noticed that it was doing well and had a hypothesis that it would do better. And we basically made the checkout experience more fluid to be able to consider those options. And what I love about Upwork is that it's very similar to Amazon, where I worked in the past, where you have to, number one, lead with the customer, but build the business case and be able to have the data to prove it's highly likely that you will have the outcome that you're seeking, right? Because we are managing our portfolio of investments as product managers, right? And so that bonus feature ended up being really helpful and successful for us as far as the key performance indicators that we were seeking outside of that, but it doesn't use AI. You know, it's something that maybe someday, but it's, we don't, it doesn't need to get that advanced to use AI to still offer value to like, Hey, um, this was useful for me. And it's funny that you say tip because it's a familiar experience for us to be asked, but it's actually very different where a tip is, um, this is where user research is so amazing. And I think it always has to be paired with. You know the quantitative data. It's the qualitative data and we have this wonderful researcher. Dr Amanda lash on my team who came from academia and came into Corporate to help us and it's just so wonderful the insights that she's helped us developed where the Cognizance of a client even is not a tip. It's not like hey, you did a good job. It's like hey, this is great I want to work with you again. Please remember me Please like save space for me where if I reach out to you like take the call you know, where it's more of a carrot, you know, it's more of like, I want to work with you again. And so we're going to continue to figure out like, what are the right features there? There's a new person coming to my team that actually joins tomorrow. Who's going to be taking that on. And so really excited just to see how we can better serve freelancers and clients to foster long-term relationships. And we think this is a tool for long-term relationships rather than just like a one-time equity boost between, you know, either party. That's awesome. Yeah. Well, excuse me, everything but tip is my main framework. Oh, no, you're good. This is like, I am pitching this internally even to, to educate people like what we've learned is we had played with the language of like, I wonder if tip is the word when you think about copy editing and with our content designer. Where you're like, no, it's just funny how you can toil over one word in a software system and it can very much change the implication of like where the user is and, and if we're matching them or not, and if the, if they see the word tip and they're like, that's not what. versus it's just so interesting. Yeah, well, as a product leader, and I love, I was gonna ask more about the user research and kind of how you think about, or gosh, there are so many product teams I've worked with that don't look at the data, or as a data and analytics person, I am hungry for the data, and kind of like, instead of making assumptions, where is the drop-off point? Like, we can watch them, like, why would we just make hunches? Can you tell us a little bit more about how you think about data in your workflow or choosing names for products or, yeah? absolutely. I think for branding and stuff, that's more like a team collaboration, but the data side is more exciting where to give credence to the people that you've met that maybe weren't able to use data, it is a cultural decision from companies to invest and allow product leaders the time and the partnership with analysts or engineers to store the data, make it cleanly queryable and. hopefully stored in one location, which this is going in the weeds for people that don't realize that everything is a choice, right? Like you could build a house that has rooms that don't have hallways or that a room that connects through a garage and isn't logical, you can build a data store in the exact same way. And so some companies might not think about reporting on the data. And if you don't tell engineering upfront as a product leader, I wanna be able to report on this easily. without a bunch of joins between tables. I want it in one table. I want it accessible within 24 hours. And I want it to be comprehensive for every single user action in this way, right? Like you have to tell them that to then be able to reference it and have it and have an analyst that knows the data and is capable enough. Like this is where I know my skills and I'm not an analyst. And to pitch up work again, this is where you can find people where if you don't need an analyst all the time, you don't need someone in your team. think about hybrid work and freelance to augment and benefit your team with an expert that can give you five hours a month and you can start to develop that data. But for me, it's paramount. Everything starts with data and this was locked into me at Amazon very early in my career because you do operational planning and I think Marion is how we connected and very early on in those teams, like we had the data, I was on the Fire Phone team, they thought like that was gonna be awesome. really was going to propel our brand. You have a bunch of data and it's a hypothesis. Right. And so the quantitative data is what's so interesting to me because you can see, like if you're walking in a forest and you see a path that everybody is going down this one path, and there's a couple of others that are lighter and there's grass, but you can tell there's a path. And you're like, well, I want to get to the river. I'm going to take this path because it's that everybody must be going down that path because it's the path most trodden. Right. And the quantitative data will look like that. And then you can see, yeah, they got to that further point. There must be a river down there. Like if you didn't have a geographical map and you were just looking at where people walked, like there's a river down there. But quantitative or qualitative, excuse me, to pair with the quantitative, that user research, if you go ask someone, what was at the end of that path? You'd be like, oh, there's a really cool climbing wall. I love to climb. There's a bunch of rocks. Like the paths that are less taken actually lead to the river. Like those are the ones to the river, but you wouldn't know that unless you had asked. And the quantitative, you can create this whole story for yourself. And I think you had mentioned this about your podcast even, where you want to launch things and you learn a lot whenever you get it out there. And if you don't have the luxury of a researcher, like I say, it's a luxury. Dr. Amanda Lash is a very intelligent woman who has leveraged a lot of skills through a PhD to bring those into corporate America for us to be able to have statistically significant and- research that we can lean on, right? Like she tells us, can we trust this or not? Is it significant or not? And then we can say, oh, that's the path to the river. We have the quantitative, we have the qualitative, and this is what we're gonna do. And bonuses was one of those, which is I think a story that a lot of people get in companies where like, is this the right thing to do? We don't wanna be asking clients to pay their freelancers more money. Let's make sure. they want this, you know, and that's good feedback as leaders. And so we had all of the data, we had a hypothesis, we launched it, we were able to see this actually like hit the mark. And we did more qualitative feedback and surveys after the feature went live to figure out how can we do even better, right? Like maybe this isn't dialed in enough for a personalized experience to each user and we could probably make it more fine tuned to meet them there. And that's work that we're going to be leaning into this year, which I believe, you know, this is, I don't think this is a feature that we have marketed, but it's like publicly, um, generally available. This is my trepidation of like a public company. Absolutely. Not trying to get you in trouble. Not our... it. I'm not trying to get myself in trouble. But I do want to give shout outs to my team of, that's all collaboration. Where I think two product leaders can often think, oh, it's all on my shoulders. I'm the product person. I have to make the call. So they go into silo mode and they think they'll make a better decision. That is the opposite of every single research that anyone has ever put out about diversity, equity, and inclusion. Better decisions are made with a team, especially a team that doesn't look like you. you know, that has different experiences. And it might take longer. You might have to converse a little bit more about, well, why do you think that and where are you coming from? But to me, it leads to better outcomes and you're able to meet your users where you're at. Absolutely, I totally agree. And those perspectives are, I love getting questioned. People ask me, I'm like, I know, I did not think that. That's gonna take us a different avenue, right? It's like, ooh, more brains in the room. Well, and I loved how you talked about like things that need AI or we think about AI for, and things that absolutely don't. Do you all have a framework of how you think about weird to implement those things or experimenting, testing kind of a lot of people are thinking about these ideas and product growth or feature. How do you all, or if you're willing to share about now. To share what's publicly available at Upwork, we have a Labs team that has very recently posted a public article led by a man named Matt Jaffe, who's just a really wonderful leader and he is spearheading the costly experiments on what type of tech should we invest in and where related to the growth lever. And we also have a new AI leader, Andrew, I forget his last name, but we had acquired a startup named called Headroom that does... computer vision AI. And so there, I wouldn't say there's a rubric or a playbook of how to do it, but we do have the ability as product leaders to pitch ideas and to make investments that are using our available engineering prowess, right? And so I could adopt AI in the area that I own that is outside of what Matt and Andrew are kind of exploring. We also have like a search leader that is. improving our next-gen experience there. But it's more around what fits for your area. How can we solve a core user problem without eating into our margins as a public company? And I think this is a subject that I'm very passionate about because there shouldn't be AI for everything. And it's the same way that you would build cloud infrastructure or you would make any engineering decision. And this goes very far in the tech You know, it's like a blonde with a bunch of pink on. You probably didn't think you were gonna hear me talk about servers and tech and total cost of ownership, but it's very important to the AI decision and as a product leader, you need to be informed or we need to be informed about responsible business decisions and AI can be very expensive, even if you're licensing it. There's also just downstream decisions after you've paid all of the money to license it where imagine in five years, You don't want to use chat GPT anymore. Your users are stuck on it, but it's too expensive. You're like, I can't afford it. We got to switch to something else. There's still switching costs, you know, like switching costs is a concept in product management where, um, like I think the best example would be a mapping API. And so an application program interface where basically an end point that you can say, I need this data, you send it to the, like you ring them up on the phone and then they send back that data. Right. And so. Okay. A map. you would say like Google Maps is the best API. There are a lot of other maps out there that are way cheaper than Google Maps. And I actually have some guesses that Lyft does not use Google Maps because whenever you search for stuff, I'm so sorry to dig at Lyft, but and they're not invested by Google. Like Uber has like Google Ventures as a backer. So they might as a strategic decision not give Google data to Lyft because it competes with Uber. And this goes really deep in the trenches of strategy and technology and stuff. If you think about it in the same way, the users notice when the app they use all the time, Google Maps, is different than the map they're using embedded in something else like Lyft. And so if you think about AI and familiarity with large language models and chat GPT, it's very good, I won't lie. I think it's better than what I've used for Bard or Google's version. And... People are going to notice if you have to switch to something else that doesn't have as high of a relevancy or precision or whatever your AI Metrics are even if they don't know what the metric is a user experience They can feel the difference right and so there's the cost of adopting it right now like I'm gonna rush and I'm gonna It's expensive, but let's just try it for three years. What are you gonna do in three years? What are you gonna try something else? Are you gonna sunset that? Are you going to actually downgrade and no longer use a feature that's exciting, that brings you monthly active users or daily active users? I think a lot of people are making cavalier decisions to adopt really expensive AI or to hire data science teams. And those are people, those are their careers. That's their livelihood. They're making a decision about themselves and their family to join your mission. And if you don't have a really thought out plan and you're selling them on a concept that's not thought through, I'm worried about the ethics of that as a human and as a leader. And so I think the adoption of AI, it's gonna have a large effect. It's going to change the world in a positive way, but I do think change should be monitored thoughtfully. And we should look at how is this affecting everyone? And is it the effects that we wanna have? And if you run really fast through a race, you don't remember the people's faces along the way, right? And so I just think sometimes it's nice to slow down and read those signs of like, you're doing great. I like this. Do you want some water? We had the Austin Marathon in the city yesterday. And so I think it's top of mind of like, but I hope that's helpful. And I hope that's like an approachable answer of the deeply rooted decisions and like the cost, the user experience and like the humanity of the people actually building it on your team. Absolutely. Gosh, I love your nature metaphors. You've got great, great examples. And I certainly... Oh gosh. You gave so many examples. I certainly experience, I think it's so interesting as people who are working on the tech in the back end, like you and me, who like we touch, we make these decisions, right? Our teams make these decisions. And then the end user experiencing Google Maps. Like I have used Google Maps and it takes me on a route. I'm like, why are we taking this route? And it's like literally shows me a business that pays for Google ads. I'm like, oh, this is why we took a detour. He'd like me to pass. I'm like, this is not in my head. But those. micro decisions of which company talks to which company, pay the monetization and thinking about future proofing of modularity, my CTO and I talk about this all the time. This is what works today, but as you mentioned with architectures, if we're calling this certain API, uh-oh, the price is skyrocketing. This no longer has an ROI for us. Do we wanna sense that the feature, do we wanna make changes? And as certainly as we're seeing all these different APIs appear overnight. and frankly, some startups launching and then are they gonna go under in three seconds? There's huge market volatility in the agency that we have to be able to choose which models, which approaches. I mean, honestly. can get really overwhelming. So before we transition to kind of your roadmap into this field, can you share maybe any surprises or learnings that you've had kind of working in this kind of product space? say the surprises have been most people come into it thinking, I don't know anything. Even the data scientists think that. And I would challenge you to have confidence that you know something that as a team member can bring value to the outcomes you're seeking. And I have been shocked and delighted by compliments I've received after collaborating with people that... I thought were just geniuses that had careers I couldn't ever fathom. And they were so grateful that I was able to share customer insights, like market insights, where there's a difference between knowing people and knowing your market and knowing tech and knowing an expertise that is applied outside of the human realm. And so that's, I think, the most surprising thing. I hear from a lot of people about feeling... like they are not supposed to be there, you know, and imposter syndrome. And I just, I think we're all imposters, you know? And so just feel comfort knowing that you know something. And there's probably an ability to learn mutually from whoever you're speaking to. Absolutely, definitely. Well, I have one more question that I want to ask before we get into your career. As you are literally working in the field and your teams are making these decisions, where do you see your part of the AI and the kind of product field headed in a bigger picture? Um, I think mine is more on the ethical approach to AI and making sure humans are in the loop and making sure users are informed upfront around their data being used and how it's being used and the modeling for it. It is a passion where, you know, before we got into the podcast, I had shared with Joan, like, this is something that's maybe not popular, um, but I, because it does slow down progress a little bit to be thinking about the ethics behind it. But, um, That's where I feel aligned with Upwork and I feel good to be at a culture that is focused on the humanity. And so I do think a lot of people are with me there, but I think that's where I think about the AI future is specifically data privacy and autonomy to the users, where their data is being developed for AI or AI is being given to them and their ability to be informed and consenting in that experience. Oh, for sure. Yeah, I know what I think, human in the loop. I mean, your marathon metaphor, I think is also like, are you running down the wrong path? Literally, are we worried? And what is progress and that finish line? Exactly. That's, I think, the question. And I think it's, we each will answer it our own, right? You know, the world's a vast place with many different cultures and progress is subjective. And I think my answer would be progress is without the loss of humanity, you know? Ooh, I love that. It sounds so big, but we're really working on it. Okay, how did you get into this career path and this job? Um, well, I graduated college at the worst time for my, um, generation in 2008 with a degree in journalism. And I moved to Seattle because I was like, this will be great. Um, and couldn't find a job and met someone at working in a bead warehouse and got a tech job and just loved it. And I've always been a science person. I've always been really into STEM, like growing up always did. Um, kind of like Super Science Saturday weekend stuff. And so it just clicked with me and I just started building and I moved from, that was Big Fish, to Microsoft, to Amazon, where I met Marion, became a product leader. I was lucky at Amazon. I was the first person hired to develop the global content policies for all of Amazon Digital as they expanded outside of the United States. So, regretfully wrote every single document and know firsthand what they are and are not allowed to sell in every single country in the world. and then invented software to be able to do the work that the humans that I managed in the US and India and China didn't have to look at it. If you think about a world before AI, humans had to moderate that. And so that was my first AI tool, was a natural language processing, Android app content review engine that helped us be able to scale the team. and allow the sweet angels that were on my team from other countries to not have to see the dark sides of the internet and the world. And like it comes through once, you'll never see it again. And so from there went on and moved into APIs and SDKs on the Fire Phone launch and the expansion of the App Store and then consulted on Jibo Robotics, which is one of the most impressive AIs that I've ever gotten to be a part of, which was very small, but it's Cynthia Brizio out of the MIT Robotics Lab. And she actually consulted on the movie AI just to make humans more approachable. And after that, I moved to a startup called Like to Know It. It's still private and they compete with Instagram on shoppable social media content and then moved to Amazon Web Services and built a really weird product to be able to partner enterprises and startups. It was a pet project of the CEO at the time and got to learn a lot about. a lot of different technology and AWS services and kind of like the innovation realm at large. And then moved to Austin and came to a company called Youship and helped them develop an AI pricing model and do some of the API mapping stuff that I had talked to you about, which was kind of interesting. And then moved to an AI startup called Disco that used AI to figure out which documents or evidence from whatever file type is relevant to a case. So helping lawyers. democratize evidence review and save a lot of money, which is funny because AI can actually help you save money if you're looking at millions of documents, it's worth the cost to only look at a couple hundred or a couple thousand, right? Which was, I learned the most about AI working there with a man named Dr. Robert Harrington, who taught me a lot. And he's the one that I think gave me the approach of you can teach people who are a lot smarter than you. And then I came to Upwork in the last year and I've been working on work management. And transparently, I don't actually own any AI right now. We contribute to other AI models that's developed around Upwork. Wow, okay. And I wanna ask you so many about these different junctures and how many, so many cool jobs you've had. Did you say you were working in a bead shop or you were in a bead shop when you... It was called Fusion Beads. My title was bead enthusiast and it had no windows. It was in Seattle. So you went to work, it was dark. Left work, it was dark. And I did it for six months where you counted beads from one bag and put it in another bag. But there was a woman there who was just really nice and we got along, we were into art and her roommate worked at Big Fish and they were like, oh, you have a degree. We can get you in. And Big Fish has done really well. They exited, they were sold for a billion dollars to Emerald Downs. So they moved more into like casino gaming, but at the time it was PC and Mac, mobile gaming, like casual open world adventure. And I learned about tech, like they gave us classes about how software was built and how like your video card runs, like the image on the screen. And then I got to help. lead an initiative to port PC and Mac games to mobile. And so I learned a lot about code in that instance, because a lot of people had been making their own game engines before that. And it was before game engines became really big. It makes me feel old, even though I'm not 40 yet, just like how quickly the world has progressed, because Big Fish created their own cloud at the time. Like I think they were trying to do with Amazon and they were like, let's try this. Amazon's doing it, we've got it. And it was just too early. Um, but it was a really interesting time. Um, and I realized my luck at being able to pivot and even being in support and moving up to be a director of product is not a journey you hear about now. A lot of people more so come into product right out of college rather than learning basically every, every different type of job in a company and then moving into it. Yeah, that's so cool. Well, and your journalism degree, do you mind if I, was that a BA? Yeah. And people are just like, she has a degree, we can get her in. That's a. I think I hope that people aren't still doing that, but it was kind of a bar of like they could have an office job. And there was a hard requirement for customer support. So just answering emails to have a four year bachelor's degree. Well and as you think about, you made the joke about like kind of the blonde who's talking about on-prem. Is there anything you wanna unpack about that to people who never- not a lot of people that look like me in the space. And I think even more so people of color, you know, like there's more people that look like me than there are someone that is maybe a woman that is not white. Um, but I still like sexism is real and you, you still get people that aren't used to seeing your face in a room. And like as much as the company I work for very much values diversity and promotes it. Um, I think like 98% of the engineers on my team are men. And there's a really awesome woman Natalia, who's a backend engineer, you know, but it's not common that you see people like me. And sometimes there, I think, is a gap in the voices that are speaking around these subjects. And people doubt that I even know what I'm talking about whenever I make a joke about on-prem. And I'm just like, okay, you know, like. it more shows about them and where they're coming from to voice that doubt and exhibit that doubt to me than the journey I know that I've had and the information I know is in my head. Yeah, absolutely. I think the latest stat I saw was like in tech, 20% of people are women and 3% are people of color or some terrible number like this, but you know, reinforced. And it's so cool that you're rising and getting to be in such a high role. When you think about different, you mentioned so many jobs and I don't know in what timeframe those specifically were, but how did you make decisions as you were? choosing different jobs, potentially choosing teams? Like would you have a decision-making framework? Like how do you think about that? I more so have a decision-making framework for how to choose a new job than leaving a job. As a woman, some of those choices were for my own safety. And I didn't have the ability to plan it out like someone else might have. And I think that shocks people that I've had more than one job that I've not felt safe and I've had to leave. And unfortunately, I still think that that's the case. But I would say for leaving a job, know where you want to be, know where you want to go, know how you want to be treated, and hold those boundaries. I think the progression of the mental health space around boundaries is really beneficial to people in a high stress, highly competitive career field. I don't think tech is the only one that exists. I think you have to be mindful around what you need and who you are as a person and know when it's time to leave. I did have a journalism professor who... This is probably the biggest thing that I took away from me. Dr. Sheri Broyles, she taped a dime on a piece of paper and wrote on it, like, start saving now. At some point in your career, you'll be challenged to question your morals and you need to have money so that you can leave and not have to sacrifice who you are. And I still carry that with me, you know? And people have helped me when I haven't had the financial stability to be able to pivot when I was in an unsafe environment, but. especially to like the people that don't feel, you know, like commonly seen, whether you're a person of color or, you know, your gender isn't like highly identified, save some money and make sure you have a backup plan. And then I think looking at a new company, to me, the biggest indicator of my happiness in a role is gonna be my direct manager, the mission of the company and the strategy of how they plan to adopt technology. Because I have a lot of really strong opinions is good technology and what is ethical around adoption. I tend to do very deep analysis and diligence to speak to people around, you know, the interview loop that I'm on, but I absolutely wanna speak to someone that looks like me and that is not in a position of power. And I wanna know what they think of the culture. And I like, recruiters are like, oh, I know, like, are you sure? And I'm like, yes, like, and not a recruiter. I wanna speak to someone. Like, especially if I could speak to a woman of color that's in a leadership role in a company and be like, how do you feel? And I hate to put that on another person that's already having a hard time just existing in the world, you know, of microaggressions, but I just think it's a really good gut check of what are you walking into and are you going to be supported and feel safe as a human being? Because if someone is, you know... feel supported and they're not the majority, you're likely gonna feel good contributing in that space. Yeah, I tend to do a lot of diligence around people I've interviewing with, and what is their background, and where have they worked, and what was their journey, and asking them specific questions around how they got there. Because to me, like behavioral has just been hammered into me probably because of my Amazon experience where... To me, the best indicator of future behavior and future performance is the past. And so as an interviewer, you're still evaluating them. And so think about the people in power that you're interviewing with and what you would wanna know from them as an employee. How do they lead? Do they think about equity? I interviewed with a startup founder and I felt honored that a former peer had reached out to me and said, "'Hey, I've thought about you for this job. Do you wanna be our first product hire?' And I did not get along well with the startup founder. Very smart, like probably a genius, but doesn't think about equity. Doesn't think it matters. Thought that I was talking about problems that are for a future day. And today's problems are about product market fit. And I just fundamentally disagree with that. I just don't think that you can start a company with culture and equity as a second thought. And I think, um, there's a lot of like really smart people out there that are making. similar statements. Yeah, I hear you. Well, and I will just say I'm sorry you didn't feel safe at work. That's totally not acceptable. And I think unfortunately, Yeah, yeah, yeah. One I will plug, I completely agree with you about emergency funds and financial education. I don't know if you follow this influencer, Tori Dunlap, Financial Feminist, but like having agency in your career, having that emergency safety net so if things do arise, hopefully you don't have to go into debt or there are other repercussions to taking care of yourself and getting out of those situations. Yeah. And I think it's good for any, any person, you know, I definitely know that like I have men in my network that feel like they have the financial burden of their family and like they endure situations that I see them just take on pain and they're like, well, I got to do it. This is the job. I have a family. I'm not going to create risk and I'm just going to endure it. And I'm not going to say anything. And I have a lot of respect for the level of strength that takes to do that. but I also think that they shouldn't have to do that and they should be able to feel happy and they can clearly make whatever choice they wanna make. But I think that having a savings account and just a security to fall back on so that you can make a choice for your own benefit is good for everyone, you know, but especially women. I love seeing that someone else is evangelizing it, so. it's a phenomenal book. Well, we'll link it in the show notes and otherwise. When you, I'd love to talk more about careers, and some people might be listening to this, and they may be like, ooh, that's exactly what I want to go into. This is really exciting to me. When you think about the shape of your team and how you all hire, because you're on the managerial part of this equation, like what are you looking for in candidates? What do you ask recruiters to be looking for? How do you consider different candidates? Yeah, well, I have a very, very senior team, and we are a core platform team. And so the technical bar is higher in our area just because they have to have a fundamental understanding of architecture to be able to partner with engineering to think about long-term scales. So problem solving is core. Having taken a very complex problem, I like to say like a scrambled up ball of yarn, you know, you're at your Nana's house and it's like, why is this yarn look like this? and they've taken it and they've rolled it up into a very clean organized ball of yarn. Oh, and there's actually three balls of yarn. And let me explain to you these different colors, you know? And so those are the types of people that excel in the team that I'm managing right now. And I do think that's a core skill for any product manager. I think the layer on my team is the technicality and having, um, just the confidence to deal with ambiguity and build bridges like across the company while managing with influence. So there's it's. people that have to demonstrate an ability to hear people and commit to a response, even if that response isn't what they wanna hear and still maintain the relationship because you can't always be everything to everyone because you have to maintain a platform that has to scale and we have to think about 10 years from now at the same time that we're thinking about today. And so prioritization is a core skill in my team that goes back to the data conversation we were having. It's why it's such a deep partnership with all of the other, you know, software development leaders where I do consider analysts product people, like a good analyst is a product person, a good researchers or product person where I call it core four. And I got this from disco startup. I was at where you have an arm of data. You have an arm of user experience design. You have engineering. So sorry, my dog sitting next to me and then you have product. And so you need all four. I'll use my phone. like for the table to be flat, right? Like a table is gonna be wonky if the legs aren't all equal, right? And so I think for my team, it's collaboration with those parties. And I cannot hire product managers that work in a silo because number one, it won't lead to good outcomes. Number two, they're not leveraging the expertise of their team. And number three, they're not gonna be able to lead with influence because if you don't partner with people, you're not gonna be able to... influence and hear what they're working on and adapt and move forward together. Yeah, absolutely. Well and I hear collaboration and also high emotional intelligence to be able to use those conversations and build relationships. The more I do business, relationships, you know, as a core skill. If people are listening to this and they're like, I really want to get into this field. What kind of action steps or advice might you offer them? Do you mean software development as a field or product management as a field? I think to be in these type of collaborative rooms, honestly. Um, I would just say boot camps or learning. There are masters programs now that you can take for product management specifically, um, product is a very unique role where a lot of people would like to do it and product management is different than product ownership. Product ownership is more so you are working directly with an engineering team and it's a much more junior job that you can find at a really large company, especially like. a saber or a super distributed, like scaled platform company. And so I try to tell people like, I got the experience in jobs before I had the title and I pitched to get the title. And so I think learn about what the skills are, like it's widely available. This is where I think it exceeds my expertise of the information you could find online from someone else who's a better educator and better at. making these concepts approachable. You can find them for free. Like MIT gives out free courses, Stanford gives out free courses, Amazon and Microsoft are giving out free courses. You can pay for a bootcamp that's a couple thousand dollars. I believe that those do fairly well at placing people in jobs. Some may do better than others. And then there's education, networking programs, like general assembly and local meetups, especially if you're in... an urban area with like a city center. I think about even smaller areas have it, but you will be able to find a meetup. I absolutely guarantee you there's people that are meeting up. They may not be your best friends. It may be very awkward and uncomfortable, but you can learn and eventually you'll meet someone that's less awkward with that you can connect with and that you can continue down your journey. I just, this is my route probably with everything is emotional intelligence connection and collaboration because you're gonna learn more from all of those other people. And you start to get the accountability of interest, where I don't have a lot of friends that are in the technology field, but I do have friends that I've found through the field that are a light in my life that helped me share that enjoyment separately from my personal life and the people that maybe I went to college with. That's fascinating, yeah. Well, I think as you're dropping great nuggets, gotta process these things. When you think about giving advice to other people as they navigate their careers, who might be just a few stages behind you, I mean, it sounds like that emergency fund and kind of the dime examples, extremely sage advice. Are there other pieces of advice that you'd strongly recommend to folks? Be patient. It can be hard to get the title you want. I think director of product is a very difficult title to achieve and I've seen people who are very ready for it and haven't been able to find the business to promote them up to that title or to land the job. I think it's easier to level up in a company you're already at. I know people don't like hearing that because it can be very difficult to show. disloyalty to your boss or to your own role, but I would challenge you to find a way to communicate that it's your journey and it's a growth journey to develop and you want to stay in your company and leverage what you already know to continue to develop. That will, you will see much better outcomes and try to find a company that's large enough to give you that equity to move around. Not every company is big enough to... be able to do that and float a job to be empty so that you can move to another job internally. That is the benefit of really big companies. But I do think patience can be a virtue and I will caveat that with everything I've said about being a woman and feeling safe, feeling seen and heard and valued for your contributions and rewarded with additional compensation or titling. comes back to safety, that's psychological safety, right? And so balance the patience with making sure it's at a time lever that is reasonable. If you're in the same role for 10 years and you're constantly asking how you can develop and you're doing it and they don't develop you, to me, I would question the psychological safety of that role and maybe find another place to move up, and so I don't wanna say like, Endless patience because sometimes, you know, you know the situation, you know, it's right for you, but it can take a while. And I think being a team player to have a conversation with your boss about growth opportunities, career development is good. I actually just hired someone on my team who is really clear that she wants to get promoted and move up to the next level. And we had really open conversations before she was hired and when she was hired about is that even a possibility? Like do we see our business growing in our area? to be able to even have the opportunity to have that level of seniority on the team. And we did the diligence internally and had an open, an honest conversation before she made the decision to join the team because that's the ethical and right thing to do as a leader, right? And so I think look for the people that are leaders that are willing to have those conversations, like challenge them in interviews. And then when you come in, have that conversation to develop because it is easier than being a cold external hire to get up to the next level. Well and I love that communication, but also longer picture of I have this goal, is this actually gonna happen here? Like, is it, like, I unfortunately have a friend who like, I don't see how he's gonna see anywhere to rise. Like his manager has held that position not moving anytime soon. So I think having that in such a short-term world, having that longer and ambitious perspective is unusual. the business has to grow, right? And if especially at director, that's a large position, you know, if you think if we were in person and fully remote, those people at Amazon had offices, which was rare, you know? And so, and not to say I'm at the same level as an Amazon director, but it's something where it can take a long time and you have to own a significant portion of the business to warrant the title. And so there's a difference between having the skill set to do the job and having the business need to fill that seat, you know, and that's where I think it's probably good advice to your peer or your friend of if there's, if the business isn't growing and they don't have a need for another director, another person, and his leader has been there for a super long time and he really wants that position, you know, like he probably needs to look elsewhere. I think that's the other challenge is if you have a really good job and you're growing, you're developing and you like your manager. how important is it for you to get the title? You know, if you're fairly compensated, you feel really good otherwise, that's where it comes back to the right decision for you. Oh, totally, and I've heard the learn, be compensated, or leave, or like there's some kind of like, know why you're there beyond the paycheck, which of course is a privilege to even be thinking beyond the day-to-day paycheck. Well, thank you, Lauren, so much for your time. If people want to continue to learn from you, are there places they can find you online or otherwise? Yeah, I'm on LinkedIn. I am experimenting with maybe posting some educational content on Instagram, but I'll post on LinkedIn if I go down that path. I really enjoyed today. You can tell it's like a passion for me to share my perspective of technology and how to grow and develop. And so I really appreciate you reaching out and setting up all this time, Joan. Thank you so much. absolutely, Lauren. Thank you so much. Cheers. Oh gosh, was that fun. Did you enjoy that episode as much as I did? Well, now be sure to check out our show notes for this episode that has tons of links and resources and our guest bio, etc. Go check it out. If you're ready to dive in to personalize your AI journey, download the free Your AI Roadmap workbook at yourairoadmap .com / workbook. Well, maybe you work at a company and you're like, hey, we want to grow in data and AI and I'd love to work with you. Please schedule an intro and sync with me at Clarity AI at hireclarity .ai. We'd love to talk to you about it. My team builds custom AI solutions, digital twins, optimizations, data, fun stuff for small and medium sized businesses. Our price points start at five, six, seven, eight figures, depends on your needs, depending on your time scales, et cetera. 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