345 - Thumbtack Redefined Leadership, Then Rewired the Company for AI (Robert Lopez, VP, Head of People, Thumbtack)

0:00You've got to complement that with other behaviors and other what we call how components, and those are building A-teams. Building A-teams is comprised of being talent obsessed, hiring fantastic talent, and developing talent so that it grows with the company. It requires cross-functional collaboration. Being a steward of how work gets done is incredibly important, and showing up as a team to do that is something we expect of leaders. and then being a values-driven citizen of the company and impacting the culture in positive ways over time and building the culture is also another component of what we define as a leadership.

0:33So between those four components, what we've instilled into the company is that they all live in harmony with each other. If you have a company with too strong of a push on delivering results at the expense of growth and development of your team, eventually you burn your team out, right? If you're too focused on values and citizenship and not enough on delivering results, Your high talent that you brought in could get bored and doesn't feel challenged. So the way that the framework works is these four components work in unison. You're listening to the Modern People Leader podcast, where we go behind the scenes with today's top HR leaders and work experts.

1:07We talk to them about how they've gotten to where they're at, what they do every day, and what they see coming next for the future of work. Hope you enjoy.

1:20Welcome, Ram. Welcome to the NPL. Thank you. It's great to be here. How's your week going? You doing good? Week is great. Whenever anybody asks me that, I've got to look and see what day it is to understand how far into the week I am. But so far, so good. It's a good hump day on Wednesday. Speaking of, guys, October is almost behind us. When did that happen? Seriously. I don't know. It happened too fast. It's going to be Thanksgiving before we know it. And then it's going to be the new year. The year's basically over in my mind. It's already 2027. Yeah, 100%. You're absolutely right. Well, with that, there's a lot of good news because a lot of if it is, but it's not quite.

2:03And so I want to talk about more recent good news. It's our first tradition of the show. We share a work or personal related story, something that's happened in the last week or two. And we prefer for our guests to go first. Yeah. Look, I brought a little show and tell because the good news for me was I finished the Marine Corps marathon on Sunday. Marathon number seven, which was fantastic. It was in Washington, D.C. It was beautiful weather. I did it with a buddy of mine for the first time. So it was the first time I actually ran with somebody else and he was his first time. And it was fantastic.

2:37It was a beautiful day. Did that make you faster or slower? I made him slower because I'd picked up an injury a few weeks ago. But in the end, it ended up working out great because we both at the very end were toast. So if he had gone faster than I was letting him, then he probably wouldn't have finished. And I would have definitely struggled across the way. But in the end, when you run a marathon, all that matters is you cross the finish line. The time only matters to you. That's what we've been hearing. Yeah. I've tried the highest. I got to like 12, 13 miles and my knee just started hurt. I got to like, that's like my breaking point.

3:11I don't know. Daniel, what's your wall? well your wall is just running in general right i used to be able to go pretty far like i could do pretty much whatever like i was a runner for like five or six years and then i started having some lingering knee pain and now i'd say my my max is like four miles yeah yeah that's and then i get the old man knees four miles 14 miles look running is a great thing i know plenty of people who only do it when they're being chased i love to do it it's my it's like my peace time it's my time i've got a house full of teenage daughters. And so getting out and running for 14, 24 miles, it's my, it's my thing.

3:48Daniel, what, what do you have for us today? My good news. Oh, easy. We onboarded a new member to the team at NPL. And so Steven hasn't even officially met them yet, but shout out to Lay. She is incredible. We interviewed a lot of people for this role. We had a lot of applicants and she's going to be helping us with one of our new business lines in the business. We're launching a community and she's going to be helping with that amongst a bunch of other things across the business. And yeah, it's been three full days of onboarding and getting her connected to Regina, who's the other person on our team.

4:32And so, yeah, very busy week, but we're excited to have Leigh on the team. Awesome. Congrats. I always am struck by the fact that people who like spend all this time looking to hire somebody get so excited at the fact that they finally hired someone. Then their mind turns to onboarding them. They're like, oh, shoot, now the real work begins. So good for you that you got her squared away in the first three days. Yeah, I had like a mini panic this past weekend because last week I was in HR tech and being at a conference all week, you basically get no work done. And so I was scrambling on Saturday and Sunday to put together a full plan.

5:09But so far, so good. Awesome. Congrats. My good news is I booked our travel for NPL Live San Francisco. And that might seem like I'm cutting it close. But this time we waited a little to finalize our plans. We usually do the same travel arrangements, but we're doing different arrangements. And that's because my wife and my son, I also have teenage daughters that are 14 and 16, but that I co-parent. And then I got married last year and have a now 10-month-old son. And they are coming with us and may make an appearance at NPL Live San Francisco. That's our live event series. And so that's really, really exciting.

5:53I haven't been as involved with NPL for the last few years. And so I'm super excited to go deep, meet our fans, listeners, meet some new people that we usually meet spontaneously. So looking forward to that. And I'm going to keep us going because Rob, I'm so interested to hear your story and the journey that led to you becoming the VP head of people at Thumbtack. For so long, HR teams have had two choices when it comes to leave. One, manage to leave internally with spreadsheets, email and disconnected systems. Or two, just completely outsource it. Tilt is now introducing a third option. Their new in-house leave management tech gives organizations the tools they need to run leave internally while simplifying admin for HR managers and employees.

6:44So you can do things like centralize leave administration in one platform, configure workflows and policies to match your org, give employees and managers clear visibility throughout the leave journey, and replace manual coordination. And if you still need extra help, organizations can also add access to Tilt's leave experts for guidance and ongoing support. If this sounds like something your company needs, you can learn more at hellotilt.com slash MPL. That's hellotilt.com slash MPL. I never know where to start the story, so I'll start at the beginning. I'm from the Midwest. I was born in Missouri and then lived in Columbia, St.

7:23Louis before effectively being raised in Boston. I lived there for 25 years or so. I went to school, I'm the youngest of four siblings that are all in the medical profession. Of course, I was the apple that fell far from the tree and ended up in the people spectrum somehow. I tripped and fell into it, like I think a lot of recruiters do, in that when I left University of Maryland, I just found my way into this recruiting space. And what I've been over the years in that regard is a moth to the flame in terms of joining companies where talent is the fulcrum of success of where that company can go.

7:56They were all at sort of inflection points of raising the bar, increasing talent density, or somehow improving their trajectory as a business on the back of the people that they wanted to go find. And so I've been a part of that for the better part of 25 years. When people ask me, like, what do you do? I'm like, I'm talent obsessed. That's what I do. I run at all these opportunities to go help a business scale itself through and with the people that they hire. So I spent time at mostly e-commerce companies, Vistaprint, Wayfair, Chewy was my last stop before coming to Thumbtack, which is more of a marketplace.

8:30But the common thread between all of them is these are all companies that were deep in their transition from early stage to scale. And doing that on the back of talent is what's always been exciting to me. And so Thumbtack, I'm very familiar with Thumbtack. We've used it in our household. How do you describe it to somebody who has never heard of them? Yeah. Thumbtack, we help homeowners find and hire the right professionals to care for your home. So most of us have had a moment, if you're a homeowner, where something breaks and we think, well, I don't even know who to call. Like I can't even figure out what's going on with whatever the thing is that just broke.

9:05So Thumbtack sits in that space. We help people figure out the next step and connect them with the right professional. And on the other side, we help local professionals, landscapers, painters, you name it, build their business by way of the connections that we introduce them to. So there's something super tangible about the mission of both helping customers and pros, and we're helping them take care of their homes and build their businesses. I was telling Steven that he probably could have used Thumbtack these last few weeks. So Steven, I'll let you share the story, but he's been operating, has his own like general contractor in his house that he's just moved into.

9:42Is that right, Steven? Yeah. I mean, it's pretty, pretty straightforward story and one that might be relatable. So my wife and I have lived in this neighborhood in Austin and we moved from a neighborhood that I never thought I would leave, but we rented. And when Elon Musk moved the Tesla headquarters to Austin, this neighborhood got taken out. So we moved to this new neighborhood. We love it. We've been waiting for four years. We finally find a house that fit our specs that was under a million dollars and that we could afford. And so we like we pounce when it came up, we get it and there's work that needs to be done.

10:25It's more than 100 years old and we get our first quote. And it was like the for the first quote, which was like a fence and some landscaping. it was going to be our entire budget, like 30k is what they quoted. And I was like, there's got to be another way. And so I have been with the help of ChatGPT, my chief of staff, and a handyman that I met here, I've been doing like knocking things out one at a time. And so like, right now, there's literally an electrician here working in the house, getting some of the red flags fixed. So definitely wish I'd known about Thumbtack. Yeah. I mean, the idea behind the company is that when you buy that first home, it didn't come with a manual, right?

11:13Nobody who had been there over the last 100 years wrote everything down for you and said, here's what you need to know about how electric is set up or whatever the plumbing system. And so we try to enter into that space, helping you figure out what to do, when to do it and who to hire to make it happen. And that's a market that is significantly fragmented. If you think about it, you just said you deferred to ChatGPT, which we have an integration to, but you defer to your chief of staff. You probably talk to some friends in the neighborhood. That's where people get their source of truth from. And we want to enter that space and solve that really difficult problem in something that's so meaningful as a massive investment like your home.

11:47So that's where we play. And so I want to jump into the conversation today. So thumbtack's big. I think I read in our prep sheet that more than a thousand employees, you're probably in multiple markets. When did you join? And tell us about what leadership looked like at the company then. And then I want to fast forward because you've done a lot of work in the space. And that's what we really want to dig into today. But tell us about the moment when you joined and that moment that you realized, whoa, maybe there's an opportunity here to make some investments. So I joined about five years ago. And when I joined, what became clear to me by way of engaging with the managers on my team was that the definition of what a leader does was very unclear, right?

12:37If you're a leader of one person, if you're a leader of a hundred people, what's expected of you, how your success is measured, what you're supposed to do and how you're supposed to show up very wildly from one team to the next. And it stands to reason, right? We were in and we are in hyper growth mode. And usually what doesn't get built is the scaffolding to help leaders scale themselves over time. And then you complement that with the fact that most leaders who are in those positions fell into them because they were excellent at what they do. And someone one day tapped them and said, go manage so-and-so and get them to be excellent like you.

13:10It follows then that like the infrastructure to help a leader become excellent at what they do. You know, when it lacks, it creates a variety of different inconsistencies and ultimately impacts the ability for the company to really perform at its maximum level. So what I believe very deeply in is that the leadership of a company creates the circumstances and the environment in which the company can achieve its ambitions. And so if you invest deeply into what a leader's capability is by way of standards and expectations and support and enablement, then you can catapult that company forward on the back of amazing leaders who inspire and motivate their teams.

13:44And so what I'm hearing is when you joined, there wasn't a company-wide definition of what it meant to be a leader. And so let's start there. Like, as you've been rethinking the definition of a leader, what does that look like in 2026? For Thumbtack, we define the role of a leader in four ways. The first thing is, and it's always the table stakes, is that the leader is responsible for delivering results. We've created this framework. And so I'll talk through the four different parts of it. They're responsible for leading a team that delivers results. And what that entails is clear expectations, clear standards, and clear direction in what is actually supposed to be achieved.

14:28Sounds like table stakes, but oftentimes leaders find themselves in a scenario where their manager told them to do something. So they're telling their team to do it. And there's this lack of connection into the why. For us, we think that having a solid foundation of understanding the why, knowing how your work connects to it, being clear on what success looks like, enables a leader to inspire the team to deliver results consistently. That's not enough though, right? You've got to complement that with other behaviors and other what we call how components, and those are building A-teams. Building A-teams is comprised of being talent obsessed, hiring fantastic talent, and developing talent so that it grows with the company.

15:03It requires cross-functional collaboration. You know, being a steward of how work gets done is incredibly important and showing up as a team to do that. is something we expect of leaders. And then being a values-driven citizen of the company, impacting the culture in positive ways over time and building the culture is also another component of what we define as a leadership. So between those four components, what we've instilled into the company is that they all live in harmony with each other. If you have a company with too strong of a push on delivering results at the expense of growth and development of your team, eventually you burn your team out, right?

15:36If you're too focused on values and citizenship and not enough on delivering results, your high talent that you brought in could get bored and doesn't feel challenged. So the way that the framework works is these four components work in unison. Sometimes you push on one versus the other based on where your team sits, but all four have to be focus areas for a leader in service of showing up and delivering the experience that their people are asking about. This is awesome. I love me a framework. And I think that simple is the more simple and straightforward, the better. And the more, I guess, understandable, the more that it makes sense.

16:15And the inner, the, the relatedness between, you know, the four components, I really, really like. And so, but let's dig into the, the four components. So what were they again? The first one's delivering results, delivering results. And so like, How did you zero in on what your four quadrants were? How did y 'all identify those? Yeah. So some of the backstory and the work that it took to get to these was we took a look at some of our highest performing leaders and we asked ourselves, what is it that we're measuring them against that gives us the confidence that they're high performing? We asked their teams, when you think about the best leaders you've ever worked for, what are the components that that leader personified that enabled you to have the success you have?

16:59It helped us land on, like you said, sort of a simple framework that was easy for folks to understand. Driving results, building A-teams, cross-functional collaboration, and values-driven citizenship. Those were the elements that both resonated deeply. They kind of held up to the standards that were already in place. And then they were also easy enough to then translate into how do we hire, right? How do we select people against this framework? How do we develop people against it? How do we promote people who exemplify it? The beauty and the simplicity of it is that it's very simple for someone to understand what it means, how it shows up and then to be assessed against it over time.

17:33And so once you establish their framework, then the next challenge that I have seen is getting that framework like embedded into the processes themselves. So not at the strategy and kind of culture level, but like in the day-to-day practicalities of how you operate And walk us through some of the ways you did that and maybe some of the challenges that you encountered along the way. Sure. Your instinct is right. It's easy to write a doc or put together a PowerPoint that says, here's our framework and then breathe no life into it. And it does. What we tried to do was be very deliberate about breathing life into it where the talent decisions actually sit.

18:14So I'll give you an example. In hiring, we implemented this framework into our selection criteria such that we look for evidence of these capabilities and people. So we'll ask leaders, tell me about a time when you developed a high-performing person to achieve more than what they were doing before. Walk us through that experience. Why? Well, that connects to building A-teams. It's not just about hiring great people. That's sometimes the easiest part. How do you take someone who has high potential and develop them? That's what sustainable talent takes. So that's one way we did that. Another way we did it is in our promotion criteria for leaders.

18:44We have an area of the document that someone has to write up that actually says, Where does this person raise the bar on delivering results or cross-functional collaboration or what have you? And we made it a requirement that people actually go back to the leadership framework and call out specific examples of where this person sets the bar or raises the bar, especially as they're trying to get to the next level. So a framework without any consequence has no legs, right? So we had to make sure that it got woven into our hiring practices, our performance practices, our promotion decisions. It really has to come to life in the actual decisions from a talent perspective.

19:17Otherwise, it carries no weight. So you create this framework with these four parts of what it means to be a leader at Thumbtack. You start to embed it throughout the company in all the different practices. How do you now know, like how do you judge whether or not you're doing a good job of actually following through with these behaviors that you want to see in the company? Do you have a way of measuring that? Is it through surveys? What are companies doing these days to make sure that leaders are exemplifying the four quadrants of leadership at Thumbtack? Yeah, that's a great question. I'm going to answer this question by also going back to the last one for a second.

20:01One of the ways that we breathe life into this was to make it very real. We launched a series, an internal kind of campaign called How Do You Lead? In which I interviewed a number of leaders across the company that were nominated by their peers or their direct teams as being standard bearers of what these elements are. And they cut across the company, they cut across levels, and being able to share specifics from them about how they orient their leadership style really helped to crystallize where the bar was. And so what ends up happening is that when you get to some of these kind of call it talent decision moments, you see the reflection of what those people talked about originally come back to them, right?

20:38You see examples of how people are setting new standards for what values-driven citizenship is by stepping up and contributing to the company in different ways. So connecting the framework to the talent decisions, to real life examples really mattered to then become self-fulfilling and having people show up in these ways. The measurable way we look into this is we run an engagement survey twice a year. And some of the questions we ask are relative to manager effectiveness. So our premise is that if we invest in setting the standard, if we invest in developing people and giving them the resources to grow as a leader, it then follows that their team should have greater trust in them and should rate them as more effective over time.

21:17And we've seen that trend significantly up and to the right. It's not as if we were working from a low base and it's kind of just skyrocketed. We were working from a base of people really enjoyed their manager, trusted their manager, but weren't getting exactly what they needed. And now we see that people feel as though their development is happening. They're being recognized for the value that they contribute and that the team is measurably better because of the people that are leading it today. So that's That's one way we measure. So if we look back, you've done a lot of work. There's a lot.

21:46You elegantly walked us through the design, the implementation, and then kind of operationalizing it. Looking back, is there anything that, knowing what you know now, that you would do a little differently? Yeah, there's always things that you would do differently. I think I would, if I were to go back, I'd put more emphasis on early practicing of how we apply the framework to real situations. So maybe that's like, you can get agreement on a sentence like, build great teams. You know, that's pretty easy. People, I think, typically understand that the harder conversation is when this leader developed or delivered a strong quarter from a results perspective, but their team has low engagement or has challenges that are sort of related to burnout or what have you.

22:33So how do you evaluate that? What feedback do we give? Like what would be meaningful improvement for that person? I think those conversations help to build shared judgment so that everybody is looking at the standards from the same perspective, not just sort of the ambitions of what it should look like, but actually what's happening in that day to day. And I think sharing some of those more candid examples of when one of the elements of that framework is out of balance, what does that look like? I think helps to breathe more life into it. And the other thing I would say is I would be more realistic about the time involved that it takes to really drive cultural change relative to leadership standards.

23:08That is a journey that takes a significant amount of time and a significant amount of investment and reinforcement from senior leaders. And I think taking a long tail approach to that enables the company to make that cultural transformation over time and that people feel like it wasn't just a document that got shipped one day. That effort's got to continue well into the future. And I think we're still still on that journey. And so speaking of the future, how do you think leadership changes here in the next few years? Is it the same? Because, you know, on the podcast, we hear all different types of takes.

23:41So for example, we had on the CHRO of citizens, and she was walking us through their four quadrant framework for leadership. It was like EQ, IQ, TQ, which stands for technical quotient, and I'm forgetting what the fourth one was, but the newest one was TQ, like thinking about how AI changes leadership. Yeah. Any thoughts there? Yeah. I think AI, I can tell you what we're experiencing here, right? AI is enabling leaders to be better leaders in a number of different dimensions. And I keep coming back to the framework, right? The ability for a leader to deliver results through and with their team now is broader because with AI fluency and adoption deeply embedded in their teams, they're able to produce more work.

24:29They're able to produce higher quality work. They're able to be more efficient in doing that. So the results that someone's actually able to achieve are much greater. When you think about the ability to build an A team in the way that we think about it here, what AI has enabled a leader to do is to inspect performance in a way that enables them to coach more consistently and to develop and deliver higher talent outcomes through their teams in a way that there's just more resource for now. So I won't go into every little element of how the framework connects to how AI has enabled it. But what I would say is that we're seeing the ability for a leader to expand and be bigger, become a consequence of AI being a part of how they operate, so long as they're adopting and fluent and setting sort of the same standards within their team.

25:09But I think the role of a leader is even more critical than it was before. And what you're capable of delivering in service of your team is that much bigger. Let's talk about that. Why is that? Like, what do you think the future might look like? Or, you know, the needs of the org changing or this, you know, what's behind this being so important in the future? And by the way, I agree. I'm just curious to get your take. Yeah, I'll give you one concrete example. And this is a personal one, actually. So I stepped into this head of people robot six months ago. And I took on a direct report remit of about eight or nine people.

25:44If you think about like classic org designs, typically they'll say like five to seven is your limit. You go beyond that and then things start to break. Well, why do they break? It's because it's really hard to remember the context that you need to share with everybody on your team, right? You're in so many meetings all day long, back to back. It is so hard for you to show up as a leader for more than five to seven people traditionally because context is the barrier. You then become the bottleneck, right? Well, what does AI do? AI has enabled me to build agents that scrape the notes from my meetings.

26:13and read emails to then tell me your head of business partnerships for your technology team should know about this conversation that happened in a totally unrelated meeting. And here's a prompt for you that cuts and pastes into your one-on-one document for you. I don't have to remember the context. I do remember what happened, but now I can show up to that person in a much more consistent way. So what's the evolution? I can now take on more direct reports. I can scale myself beyond what traditional spans and layers look like because AI enables me to consume more in organized context in a way that enables the team in the end.

26:45So that's just one example. Just continuing down that thread, is this something that the company is thinking about training managers on? Like how to build like that contextual glue with AI? Because it's definitely a muscle. Like we are very AI pilled at MPL. And so for the past few years, like everything we do is in a more efficient, like modern way. And so we have granola notes for everything. We have a foldering system. We have a system that like scrapes the notes and pulls it into the right place at the right time. But it's easy for us because we're a small team. I imagine it's much harder at a company like Thumbtack when you have 1 ,200 employees.

27:31I feel like these days, Cloud and ChatGPT can get you surprisingly far in HR work. And they're great. Until you need live people data, or you need data from performance, comps, surveys. Then suddenly you're exporting CSVs, you're explaining the company's entire history, and you're figuring out what's actually safe to share with who. And that's the gap that Shapes is closing. Shapes basically brings that AI experience directly into the HR platform. with your live people data, your org context, and your existing permissions built in. So instead of jumping between systems, people teams can build things like a flight risk dashboard, a reorg simulator, a calibration grid, or a completely custom workflow or visualization.

28:16You just describe what you need, and Shapes builds it from the people data that's already there. It's kind of like Claude and your HRAS had a baby. If you want to see what this actually looks like in practice, go book a demo of the shapes. You can find a link in the show notes. Yeah, it's super challenging to make sure that I think the biggest challenge that we're facing is in our path of AI evolution. We started with encouraging people to experiment, right? Here's a chat GPT license. Just go test and see how it works, right? That then quickly evolved into setting common expectations so that everybody was using AI consequential work and applying human judgment to it and sharing their learnings, which has then lent itself to higher proficiency and outcomes.

28:59What's missing is this ability for people to have the right skills, plugins, and ultimately context layer that enables you to come in and sit down at your desk or at home where we work fully remote and have everything you need without having to go find the skill that helps you just, for example, debrief on your interview, right? Or find the skill that helps you know how to summarize a document into a two-page thing. So what's really critical for us right now we're working on is creating the right plugin structure so that everybody by role type has exactly what they need for the composition of their role without having to guess.

29:34And that way they can just get right into the work and get right into the tool so that they are producing right out of the gate. And by plugin structure, like for me, I can explain what my plugin structure looks like or what I think you mean by that. So we use tools like Slack, Granola, Google Workspace. We were using something called PipeDrive as our CRM. Now we've built our own CRM and all of those are connected through the APIs. Is that what you mean by plugins? That's exactly right. So I'll give you an example at a rule level to help bring it to life, right? So if you're a recruiter on the team and you start at Thumbtack tomorrow, what you should walk into, no different than having access to Chrome on your computer, is you should be able to walk into your Cloud experience or your Codex experience and get to work right away.

30:25What surfaces in the back or what sets in the background is this connected layer of skills and yeah, plugins and systems that connect through an MPC server so that you yourself don't have to wonder about how do I find what it is that I need to do. I simply can go into Cloud and say, what's the pipeline report for my open rec? And it pulls in the information from Ashby. It consolidates that into a constant or consistent framework and then presents it for you to share with your leader as long as you apply your human judgment. That sort of context later, that plugin layer is something that we believe is really important to create standard for people so that there's no guesswork.

31:00That way you know what you need without even having to figure out what it is that you need. I love that. I started a job around mid-August And it took till about, I don't know, early September, early to mid September for me to have like everything I needed fully configured and set up for me to be like the most efficient. And that included like vibe coding, you know, a CRM as well. And it took way too long. I remember thinking like this just needs to be in the future. in the very, very near future, there's going to be, I think there's going to be an acceleration of hiring a new kind of employee, a different type of employee.

31:50Some may call it like the high impact individual contributor. There are a lot of different things that people are referring to this new type of employee. And I think there's going to be a like need, a competitive need to get people seamlessly onboarded. And what I'm hearing from you, Rob, is it feels like y 'all are thinking about these sorts of things. And I think this is the first time that we've talked about this. So thank you for sharing these details. It's super cool. Is there anything like this that you guys are also working on that you can share? I'm just out of curiosity. I'll talk about another example in a minute, but I think maybe the best illustration of our vision for what this connected context layer is, when you open your iPhone or your Android, it has the vast majority of what you need, right?

32:38You can go find more apps and download them, right? But you just use it. Everything's there. If you want a message, if you want to call someone, if you want to search the web, everything is where you need it. That's the same kind of experience we expect to create for people when it comes to the AI tools that they don't even know that they need, right? So if I sit down in my new role and I have this in a box experience, I might have linear, for example, for my project management because I'm a TPM, right? Or I might have whisper flow because I dictate a lot of my legal knowledge into a tool that helps me create the right contract.

33:10So what we're really trying to do is solve the problem of, I don't know where to go to find what I need. And so I don't need to go build it all myself. It should exist for me. And that limits the churn that comes with having to figure all these things out. So that's our vision for it. In terms of another example of where we're trying to create similar output in terms of better outcomes is in our actual people team. One of our focus areas in our AI transformation is that we want to make HR transactions invisible to enable human judgment to be what it is that leaders value. So what does that mean?

33:45Well, you should be able to press a button if you want to open a rack and not have to necessarily talk to them. If you need to, great, there's somebody for you. But you should be able but press a button, type in what it is that you need based on prompts. And then a wreck magically gets created in Workday and flows to the recruiting team without people having to get into the way of that. That sort of seamless experience that I think we all probably crave in every element of our life of like the transaction is simple. Maybe it doesn't even require you to do it. It just does it is what our aspiration is for our people team experience over time.

34:16I think that's a great aspiration because if you think about like what people experience is you want to be in a flow. Like I want to crush work and just get what I need to get done. Like I want what I'm responsible for. I want to knock it out as quickly as I can. And I want to work on cool things with the rest of my time. And I just think that's going to be super appealing in the future. One thing on our roadmap is calling the front door, which serves not just as the answers to questions you might have, but actually takes the actions to resolve the thing that you need. So simplest example is, how do I change my benefit?

34:54I just had a child and I need to get my child on the benefits. In most organizations today, you've got to go talk to somebody either in benefits or HRVP if you're lucky who you know who to talk to. What we expect is that you get to walk through this front door, to use the home analogy of Thumbtack, and it's there for you. You type in, I've had a child. I want to add them to my benefits. Great. The agent walks you through the process. And of course, there's probably like a human judgment layer that needs to QA this before we scale it. But that one front door is one aspiration where we think that enables us to make the people experience of working at a company that much more effective so that it frees you as the person to just go do your job really well.

35:31And so this might be what you're describing with the front door. But if we go back to, you know, the metaphor of like iPhone, you open your iPhone, you have these preloaded apps. Maybe it's like your phone, it's text messages, iTunes, Apple Music. I didn't nobody uses it anymore, whatever, like the 10 apps are that will give you what you need. Is that what the front door is like? I'm trying to imagine if like what this experience looks like for an employee, like are they logging into their computer and it has just done a very good job of, of tailoring their setup to them? Or is it through the front door?

36:13Is that the entryway? We don't know yet. We want to test this, but one of our hypotheses is that we need to put the front door where people engage at first, right? So what they do is they go to Claude or Codex and they ask the question, where's the policy on changing my benefits, right? Well, if that's where they go to enter the front door, that's where the front door needs to be. What we don't want to probably go do is build this whole other separate ecosystem where it's not natural for them to engage in. So for example, like we don't want them to have to go to a wiki to go find this. The front door should be where they're already at.

36:44And so all that it requires is you typing in the answer or typing in the question. And then the front door sort of reveals itself to you metaphorically in the background where it's now walking you through the flow. It's walking you through the workflow that's been transformed and AI enabled. So yeah, the best way to describe it is it's not making HR invisible. Whenever I say that, people have a negative connotation to it. It's making the parts of HR that are full of friction, frictionless. so you can just do your job really well and get your things resolved. And so I want to shift back to the transformation that we were talking about earlier and the importance that fluency played in that.

37:27And so what were some of the things that y 'all did that you feel like were the best investments when it comes to fluency? One, we gave people access to tools that they were asking for. It came at a great expense, right? We ended up probably spending more than we maybe needed to or could justify. But what it did was that, you know, when you tell a company, when you tell your people, go experiment, but then you don't give them the tools that they need to experiment with, you can't expect any sort of behavioral change. So we were on the frontier, the bleeding edge of, you know, ChatGPT rolling out and Granola rolling out and moving from our prior ATS to Ashby because it was AI enabled.

38:04And we just kept on telling people, keep testing, keep learning, but also keep sharing. because the reinforcing learning mechanism is seeing these things come to life. The next step in the evolution was great. Now that there's a clear floor being set, we have to describe what that floor is in terms of expectations. And so those were using AI and consequential work, applying human judgment, sharing your learnings. And so by setting expectations of how people engage from a behavioral perspective, not a performance perspective, from a behavioral perspective, We then lowered the psychological barrier of people getting involved and getting engaged.

38:38We didn't make it about, you need to do this and we're checking your tokens. We did it about, there's an existential opportunity for the company to transform. And your ability to help navigate that depends on you experimenting and learning and growing. We complemented that with a lot of L &D enablement. We created frameworks for people and trainings and enablement. But then fast forward a year later, and all of this happened, by the way, within the span of a year. It's how fast AI enablement can actually happen. we started to see that our engagement scores relative to proficiency and AI usage were like 90 out of 100.

39:10We were incredible. One of the interesting things about that, it's not all great news. Part of it is if you ask somebody how they feel about their own productivity, they're like, it's amazing. It's through the roof. My productivity is great. If you ask them how they get AI from other people, they're like, it sucks. It's crap. There's so much slop. I don't know. So I don't know what to make of the fact that there's like this, I do great, but maybe not everybody. Point being though, we made it part of our ambition as a company in terms of our scale and our ability to grow that everybody had to experiment and then adopt and become fluent.

39:38And now that's enabled us to get to this place where we're able to look at workflows and transform them and look at teams and transform them, look at roles and redefine them because everybody's been a part of this journey for a long time. If you're comfortable sharing, I would love to hear what that looks like for the people team? Like, have you begun any of that work of transforming the workflows? And yeah, what's some of the next level stuff that y 'all are working on? Yeah, it's really, this goes all the way back to the leadership framework, right? I'm going to tie it to that. When you set ambition for a team and you have high talent, it's going to amaze you as a leader every single time what that talent's capable of doing, right?

40:16I think leaders tend to be a bit more protectionist of their team saying, I don't want to put the expectations on them because they're so busy, right? But high talent wants to be pushed and they want to see what they can achieve. And so we've set the expectation with the people team, same as the rest of the company, that we're going to set the bar in terms of experimentation and adoption and launching new things. And there's so many amazing examples, some of which might sound, when I share, incremental and small, but have made a huge impact. I'll give you one example. One of the biggest friction points of our performance review process is not going to surprise anybody.

40:50It's actually writing the review, right? Well, we created a skill. It was actually at the time, it wasn't called a skill. It was called something else in chat GPT. I forget what it was called. But basically what it enabled everybody to do was provide it with the feedback, provide it with the information that are sort of like expectations of the role based on our functional level guides and not apply any judgment, but write a consistent and compelling narrative for performance. I can tell you of the 1 ,300 people that work at Thumbtack, I can't imagine more than five have an English lit degree.

41:21So the ability to write a compelling performance review is actually really limited. And what happens? Well, the person who gets the review gets a less than stellar experience. So just creating the shared skill of here's how you write a great review, not making judgments, not creating summaries, but really just taking the inputs and making a compelling review for somebody enabled folks to get feedback they weren't getting before and we measured that and we saw huge gains from something as small as one person sitting there saying i'm going to create a skill that enabled transformation for everybody across the company there's examples like that and there's examples of like total workflow redesign we have a people labs team that was born out of all of this and then where we took our some hr business partners we took some data scientists we've taken an lmd person and now they're helping the business transform workflows.

42:07Again, it's as a leader, it's your job to inspire and motivate and get the heck out of the way. And it's been amazing to see what the people team here has been able to conceive of and drive towards. And it's just, it's very pride-moking. First of all, kudos to your team. Like that, there's a ton of, we already talked through one major transformation with the four quadrant work that we talked about earlier. And in addition to that, operationally changing the way that you do things to embrace, you know, this kind of generational technology that you've done a lot. We talked to a lot of companies, and I think there's a lot to be proud of in terms of what y 'all have done.

42:52But to you, kudos as well for having kind of a vision, coherent, cohesive vision for what an employee experience could look like in the AI era. Like, I feel like we were all still in between what was and what will be. And this is one of the few conversations where I feel like I am leaving with a different kind of vision or picture for like what onboarding will look like, you know, and it's like, boom, what are your MCP? What are your preferences? And it's like, do, do, do, do, do, do, do, do, do. Here's what you have for what you're going to need for your job specifically. Boom, boom, boom, boom, boom.

43:39I just think that, you know, this again, you know, kudos to you and to the team. Daniel, were you going to say something? I thought, no, I just, I just keep thinking back to the idea of opening your MacBook or opening your iPhone package. And I remember like, you know, being onboarded to some companies and you receive your computer, they ship it to your door, you open it, you have like a couple of preloaded apps, like the bare minimum. And then slowly over the next couple of weeks, you're getting onboarded to the rest of the tool stack, which is great. But now rather than a tool stack it's like this as you were putting it like you're getting like your llm with all of your skills built in and those are connected context layer exactly connected context layer yeah yeah exactly i appreciate the kudos steven i can't take it the t a leader without a team is somebody standing in a room by themselves well that's why i started with the team that's why i started with the team it's good it's not just the people team like i give a lot of credit to our technology org for thinking big.

44:45I give a lot of credit to our CEO for having an audacious perspective on these things. And I think one of the galvanizing moments for all of us was when we said, look, we can either look at the world as we want it to be, or we can go create the world as we want it to be. We have the opportunity now with AI to do that. Yes, it comes with a lot of other challenges and we're going to run those down as soon as we see them, but we have to be a part of what the future, we have to be a part of creating the future we want for our teams. And it's the teams that really make that come to life. So, I mean, yeah, I'm incredibly proud of what they've all done.

45:15You know, not everything is like pink roses and glitter and rainbows. Is there, I'm just curious, no need to really kind of look back to the past, but are there any current challenges that you can think of that you're going to need to overcome as an organization to take the gains and your performance and usage to the next level? People leaders want to hire the best talent, regardless of citizenship or where that person is from. But when you're hiring across the globe, finding the right person is only half the battle. It's everything that comes after that can get really complicated. Can we hire this person?

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46:39So instead of immigration becoming another thing your team has to constantly follow up on, you get more visibility, faster answers, and fewer surprises. If you want to schedule a free consultation with Manifest, just click the link in the show notes. I'll look back and forward. It is really difficult once people have learned the value and have experienced the value of what AI can contribute to their work to maintain the same high quality output that human judgment alone can provide. And when you see examples of when something is provided to you and it's like cotton paste right out of whatever tool it came from, controlling for that was something we probably could have put more effort into earlier so that if you got a two-page doc before and now you're getting a 10-page doc, we probably could have created some sort of skill that would have enabled that to not be the case.

47:27But it's also behavioral. We want to make sure that we should have probably spent some more time helping people understand what the human judgment component of expectations were and breathe life into that. And so we're seeing the results of that in our engagement school where people are saying like, hey, the output I'm getting from other people isn't exactly where I want it to be. So there's more to do there. Do you have a point? You have a thought, Daniel? No, no, no. I was going to add on to that. Something that we haven't talked about on the podcast is in the past, you know, you would have a role and let's just use the example of an SDR on a sales team.

48:01Every SDR is going to follow the same process. There's going to be some sort of SOP. You're going to build your list in Sales Navigator, and then you're going to pull that into Apollo, and then you're going to send out your emails, and then you're going to make sure it's all synced to the Salesforce, and et cetera, et cetera, et cetera. And that worked for the longest time. Over the last 12, 18 months, we've rethought our workflows and come up with a new process several times for some of the same workflows. And it's not because they were broken. It's just like we keep finding ways of making them better and better.

48:45And so when we onboard people, this is something that I'm currently struggling with right now. If the process is constantly evolving, like how do you set like these, how do you keep iterating on the operating procedures and make it easy for people to understand it when they join? And so it really, it's a question, like, is this something that people are struggling with or is this just like a Daniel problem? I think it is one page from a big book of all the things that people are struggling with AI, right? That's one. I'll give you another example from yesterday from our conversation about this.

49:22When you give people the tools and then they start to see the value, and then they start to build the products themselves, it creates so much more output that time becomes compressed even more. Your capacity to do more actually gets limited by how much more AI is doing for you. And so what we see is people saying, I don't have the time to experiment anymore. I did, and now I've built this thing, and now I've got to maintain it like I'm a product manager. So there's like all of these, I find them fascinating and interesting. I think people can probably be equally as frustrated about it, but there's all of these consequential outcomes that are hard to imagine until you get into the use cases.

49:57But I'm inspired by those. Like I'm inspired to go tackle them because there's, I think just as equal of an opportunity to go continue making things even better. But yeah, I think what your experience is one of those frustrations and to your questions, even about like, what isn't so rosy, things like that. It's a good example of how a great and powerful tool can actually create more work for people that diminishes their overall capacity. Yeah, there's so much. I feel like we could have a whole episode, like maybe a group episode opportunity, Daniel, on just like weird, unexpected things that AI is doing in the workplace, just like in terms of the dynamics of how you work together.

50:42And I don't know, because there's some quirks I could share from my most recent experience that I just never thought that would be the issue. I thought it would be other issues, but not that. Because Daniel, again, we were co-founders. We've been co-workers, but it's a very kind of unique thing that we do. And so anyhow, I would love to dig into that more. But unfortunately, we got to get both of you out of here. We have a couple of more traditions. Next one is what we call rapid fire questions. Same set of questions we ask every guest. You ready to do this? Let's do it. All right. Question one.

51:21What's one piece of advice you give to someone in HR who's just starting their career? Get close to the business. Know how it works. Know what it does. Know why it matters. That way you can make better people decisions every day. If your people team gave you a superpower nickname, what would it be? I think they would say the potential spotter. I just believe in the potential of people in ways that sometimes they don't even see in themselves because some one time, actually many times people did that for me. And I love being the catalyst for that kind of growth. Okay. What a cool thing to pay back.

51:58Next question. What's a strategy or practice from another company you'd love to steal? Yeah. Yeah, I'm super intrigued by companies, even companies our size, that make internal talent movement work really well. I think that's one dimension of talent strategy that is way underserved, that doesn't matter the size of the company. Like if you've got great people, you got to bet on them and help move them around. Yeah, I was at HR Tech last week, like as I said, and that was probably the number one topic that I heard across the week. Who should we have onto the show next? Are there two or three people leaders that come to mind or even one?

52:33People leaders. I was actually going to go in a different direction. I was going to take you towards a non-people leader. Yeah. I'm going to brag on this guy for a minute, but Tim Carter, who's one of our VPs of Eng here, he leads our platform and tools organization. He's helped lead the AI transformation from a technical perspective, but with such a strong bend towards what people need that it just sort of brings to life what actually it takes of a company to transform itself. So he's somebody who I think I would give, yeah, a lot of airways to. that would be a cool i would love to have a chat with him so that would be an amazing intro and that brings us to our last tradition we call it one word or phrase close a word or a few words just to summarize you know the last hour we spent together and we prefer for our guests to go first okay uh i'll cheat because i say this in front of my team all the time onwards and upwards There's only onwards to go and upwards to get.

53:29So let's go do it. I'm going to go with contextual context. Wait, what was it? I screwed it up. Context layer? Yes, that's what I'm going with. And I'm going to say build A teams. I like it. No, no, sorry. Sorry. I just saw my notes. Connected context layers. Connected context. Connected context layer. Well, Rob, this has been such a fun conversation. Thank you for joining us. Thanks for sharing all the cool things y 'all are up to at Thumbtack. It's been a great, a great one. I appreciate it. Thanks for the time, guys. I really enjoyed the conversation today. Great to talk to you, Rob. Bye. Thanks for tuning in to another episode of the Modern People Leader.

54:13We really, really appreciate it. And if you enjoyed the show, please leave us a five-star rating. It would mean the world to us. and connect with us on LinkedIn. We want to know what you think about the show and you can find links to both of our profiles in the show notes. Thanks again for listening and see you on the next episode.