Are startup HR teams okay?

0:04Today on Great Chat, we look at some of the changes brought on by AI from the lens of people ops. What are leaders doing to recruit and retain top talent in this moment, and how does it differ from past times where employees had more power? I'm Helen, and this week I'm joined by Ashley and guest host Emily, HR evangelist at Rippling. Great Chat is brought to you by Mercury, radically different banking loved by over 300 ,000 entrepreneurs. We use Mercury to run this podcast and love recommending it to other founders and fund managers. It's free to get started. Try it for yourself. Visit mercury.com to learn more and apply online in minutes.

0:40Hey, welcome, Emily. Thank you. Excited to be here. Welcome to the pod. All right. So what happened this week? I will start because I feel like my feed is probably more clarked with this than both of yours. But yesterday, another AI CMO dropped. And, you know, it was like a new agent that does a lot of really clever optimizations for ads. And so this is what we think CMOs do. And I feel like what was different about this one is there was another one that said last year that they were an AI CMO. It was Icon. And they famously raised a ton of money and then like spent like four million dollars buying the domain which i feel like is now icon.com baby icon.com which now friend.com ai.com this is a this is a trend but i think they crashed out and so i think this time when another ai cmo dropped you know uh people were skeptical or like a lot of people ran to try it out and like we're pretty disappointed so um in this you know we talk about this like 2026 vibe shift, like all the, all the tactics from 2025, like when, when they are attempted this year, they're just like falling a little flatter.

1:58Um, or yeah, they're just not landing. And like, I felt like we had a whole cycle in a, in a 24 hour period. I just think like calling it an AI CMO is both clever because it's going to get people's attention and it's controversial and it's like, Oh my gosh, the CMO is a highly strategic role. and you've like made it into an agent, but you're also setting a really high bar for the product. And so when the product falls short, like it's just like, what do you want? Do you want the attention or do you want the appropriate expectations for someone coming in? And then you do kind of box yourself in on who your customer is going to be because calling yourself an AICMO is alienating to people who are actually running marketing teams.

2:41So you're basically running to the people who don't believe in the value of marketing. Such a great point. So that is the point I make all the time, which is if they are wildly successful, eventually they have to move up market and not sell to startups who hate CMOs or hate marketing or like don't want it. And they have to eventually sell to CMOs. And then it gets awkward. You know, I've been positioning myself as displacing you and your team for years. But now that I'm moving up market, hello, please give me money. So it's fun to watch. I saw an interesting insight whenever these tools drop, because I think there's, from an HR perspective, there's a lot of AI, HR, bots, agents, everything coming out.

3:24And it's just like, they're not being built by the HR person or the marketing person. So there's this just like really fascinating disconnect of like selling and promoting something that is not actually built on the understanding of what the work actually is. And that gives me cause constantly. I love it. I love it. I love it because it's like, you know, insert joke here about like a CMO at a startup's like real role is like, you know, coming in and picking up all the debt that has accumulated from like not having marketing for so many years. Or there's another joke about like, I hope they're not on annual contracts because so few CMOs make it to a year.

4:06So if it's an AI CMO, it's like, do they churn out at the same rate too? You know, it's so it's just, it's just like a nice reminder for me. Who's no longer CMOing like, ah, this persists. Maybe that's a good transition to talk about. Well, first of all, rumored meta layoffs, 20 % of the company. But you know, this is, this is where we're seeing like a trend that we'll probably get into later in this podcast of like people having to train their replacements. And by replacements, I mean AI. And so I think that this is, Emily, what you just said, it's not the CMO generally who's being replaced by AI.

4:47This is just like clever or not so clever marketing, depending on how we want to look at it. But it's like the sort of more entry level people who are like, you know, creating the process docs that will enable AI to take their job someday. And I think the meta rumors are still rumored, but also seem kind of inevitable. I mean, we talked about this a couple of podcasts ago when Jack did the 40 % cuts that block, how that was going to give the rest of the industry permission to do this. But yeah, I feel like I'm less worried if I'm the CMO. I mean, if you're the CMO, you're worried for different reasons, as Han said, given the turnover of that.

5:27But for younger people, it must be just such a weird time. It must be crazy because also I feel like younger people, we have this natural cohesion, right, where like younger people do tend to be the most tech forward. But at the same time, the tech is what's starting to displace them. And we're like, I almost like I feel like these decisions are a little short sighted. And this might be like, the bigger question is like, if you're going to cut off 40 20 % of your workforce. Okay, like, that's fine. But like, what is the ultimate plan? Like, who what is the talent pool you're going to plan to hire from for the next 1020 years?

6:05Is it going to be a hybrid agent workforce or do you have to totally remodel your concept of internships and entry level work because you now need to train some basic professional skills and like navigating a workplace? It creates like a much bigger question in my mind than just like, oh, we're replacing jobs. It's much more of like, OK, but where are we five to 10 years from now after we've made these decisions? Where are we going? That's such a great point. You're not looking that far out, Emily. That's what it feels like. That's totally true. So like a sales leader I really admire was saying like, gosh, you know, like he's been saying this for like a year where he's like all of these AISDR companies, it's great.

6:46Cool. But SDR is like such a great role to train AEs, right? And to train like future sales leaders. So like now what's the path? And so that's so interesting. I wonder if in a couple of years, like we'll just start seeing these gaps, right? where it's like you have these really senior folks and the sort of like gap. It also, I forget where I was reading this, but like the, I wonder if it's one of the Substack articles, Ashley, maybe you shared in here was like talking about how AI is just creating it. Like it's much easier to iterate and like problem solve brainstorm, right? It happens so quickly.

7:29So the job is turning from doing that work into like making those analyses decisions off of a bunch of other work. And it's so that to me is also changing what entry level work is, is it's no longer doing the grunt work of digging through things. You're starting to make those business impacting decisions at a lot earlier of a stage in your career because that's what's bubbling up to you. And so it's also how do you build that judgment for someone who hasn't had the years of sorting through the data to understand the real implications? Like, yeah, it's a fascinating workforce conundrum. Yeah. Oh my gosh.

8:06And also, I mean, I think all three of us can imagine with some degree of horror, like what happens when every person in an organization has the ability to just make those like high level, like how do you coordinate all of that? Right. And it becomes like a huge orchestration problem. I saw an interesting post on LinkedIn the other day, and I apologize, I can't remember who it was from. But someone was saying there's nothing more painful than watching an engineering task to ship a product go from weeks of work to six hours, but then seeing it wait for another six weeks in the queue before it can be pushed.

8:47Because we have all these tools to make work faster, but we haven't solved that orchestration problem within companies. And so it's one thing to say, oh, everyone's just empowered now because the execution piece has been solved. But then how do you actually operationalize that within a company? I mean, I think it's probably easy at a really small startup with a handful of people where everyone's sort of like working on the same thing and really challenging at a company like a rippling size or really any size over like 50, 100 people. one really interesting thing I saw and this can get us into the like Travis Kalanick is back discussion Helen I was thinking of you because I was listening to one of the I think it was like a TBN clip with Travis which also just made me smile because like Travis is made for the TBPN era of tech media but he was I think it was last week where you were or a couple weeks ago where you were sort of pounding the table around like don't build in public when you're a startup.

9:51And obviously Travis has some battle scars from his Uber time and like being very exposed and having a lot of palace intrigue out there. But he was saying like there's something really powerful about stealth mode. Not just it gives you the opportunity to mix things up a bunch, which seems like might be the case. I still can't tell if like Cloud Kitchens is actually just sort of like pivoted to being Adams or what the trajectory is. But he was saying that, you know, building and stealth helps you select for people who don't need external validation and are focused on the work and focused on building.

10:29And that is a huge vibe shift because I think we've been in this era of like performative everything, right? Are you even building if you're not tweeting about building or tweeting about your open cloth setup or tweeting about 996? And so it's been the performance has almost like superseded the actual doing. And I saw someone's commentary around like Travis is bringing raw intensity back to tech. And, you know, who knows? But I was like, yeah, actually, it feels like we've had performative intensity. And I'm sure there is some like raw intensity, but it's been. What did you think of his manifesto?

11:10I am. So dramatic. I mean, it was definitely so dramatic. I was like, do you need a hug? Listen, I think like the drama plays to this moment. And I think that there are a lot of people who are ready for a Travis comeback. And the context of when he was ousted, which I believe is 2017. Does that sound right? Around then? is like so different than the context today. Like, you know, if Susan Fowler dropped her bombshell essay today, would it even make a no, would anyone even care? And so anyway, so like the context, the environment is so ripe for this story. So I wasn't surprised he like played into that.

12:03He didn't specifically call out Benchmark or Bill Gurley, But like everyone who was around 10 years ago and maybe even more recently knew what he was referring to. But then it got kind of weird. And I feel like this is what happens when founders spend a little bit too much time alone in a room with their thoughts versus putting them out into the world. But who knows, maybe the uncovered truths resonated with an audience that I'm just not in. To your point of like, what is Adams? is it just a renaming of cloud kitchens perhaps but um no it's exciting and i think that uh i think it has to do with like delivery i think he's i heard he's like autonomous robotic last mile delivery of the food produced in the cloud kitchens perhaps so maybe it's all tied together every piece of the value chain.

13:02AI for the physical world, Helen. That's the vision. I mean, I think it's an exciting problem space and I'm sure it's intentional to breadcrumb us a bit and have this like very expansive,

13:19ambiguous articulation of what Adams is about. And then as we go, we'll have more details and more information. So yeah, so I think it was, I mean, very successful as a comeback launch. Definitely left a lot of us wanting more, but that's like a good place to leave us. Adam Newman also had a comeback. Oh yeah. The video of the flow space. Yeah. Yeah. Yeah. So he had a comeback. And who else did we see? I feel like this week was, it was like right for comebacks. Well, I mean, the whole Uber cast is back, right? So it's not just Travis. It's like Emile Michael is in the Department of War, like talking about aerobic.

14:06Right. Shervin Peshever is weighing in on Iran. And then Bill Gurley is on his book tour. Book tour, yeah. I have a copy. Wow. 2017 Ashley never could have imagined. fast forward to today. Oh my gosh. That this would be where we are. But I guess congrats to all of them for having some very interesting staying power. Do you feel like any of them were introspective in the past 10 years? Oh my gosh. So Mark Andreessen did a podcast, uh the founders podcast david center a great podcast um and there's a clip from it where uh i think he he says something to the effect of he tries not to be introspective or maybe even too introspective because he's just focused on progress he tries to be as yes as little as possible i think that's what he says and i did not listen to the whole thing so i also said it was a modern concept like that it like it was sort of invented alongside like therapy I think the subtext now see yes exactly now seeing all of the follow-up tweets because it's like wow for someone who's not introspective you really want to dig your heels yeah you really thought about this one um it seems like this is a little bit of a pushback on like you know the therapy culture we've had or like a lot of um the softening of men you know last week Ashley saying that the is the masculine era and maybe you know uh well that's that but yes yes yes but it's like maybe you know we're saying instead of going to therapy you should you should channel all of that anxiety and go to war yes and start companies and make you know vcs a lot of money be in the arena which like is all fine and well but like to what end right like are you like if you are dead set on making the most money like that's that's awesome congratulations but like what else do you have going for you and like what else do you have i don't know i'm of the mindset like you might be a little happier you you already have the money so like introspection might be an interesting activity to tackle you can it is you know you can spend as if happiness is the goal yeah yeah exactly exactly twitter is not exactly the collection of like the happiest people I thought it was maybe Helen just to continue the context setting.

16:38So, you know, it started with Mark saying that he, you know, tries to be as, to avoid introspection as much as possible. And then interviewers saying, like, actually, this is something that's common across great men of history. And so then they were talking about how, like, you know, this is a modern concept and people didn't used to, like, you know, moan and think about their feelings. and also I just have to say there's nothing funnier than talking about the great men of history with the with the sort of built-in assumption that you are one of them that very much amused me but of course like like this was such twitter bait because first of all men love talking about the great men of history but also there are so many examples of deeply introspective great men of history who actually, you know, started entire philosophies and wrote books.

17:30And, you know, so it was just like perfect, perfect Twitter bait. And then like Mark doubled down, but was doing it in a kind of a intentionally trollish way. It was very entertaining. Like I had my, I had my popcorn and I was just watching, watching the show. Just like even saying great men of history. I'm like, that doesn't have the positive connotation that you think it does like if we look at the great like i don't think they're all like stacking up to where we think they are but in terms of introspection like einstein deeply introspective deeply introspective so oh yes there have been a lot people have been doing a great job of like you know citing a long list of people and like evidence that they are quite introspective.

18:19Benjamin, Franklin, Napoleon, yeah, writing long letters to his wife. Yeah, all of this stuff, but I digress. But it is a good example of like the playbook for how to fight online, which has never cede any, don't cede an inch. Like Mark Andreessen, instead of acknowledging that there might be some good counterpoints, just like double down ferociously. And, and that is, that is how you fight on the internet in, in 2026. So, and, and yes, it makes for good entertainment and a lot of engagement. Things move very quickly, understatement, in, in AI right now. And, you know, keeping up with potential reductions in force, like at Meta, today's Tuesday, they haven't done it, even though I guess the rumors have been moving for a couple of days.

19:07And of course, Block did their, did their big layoffs a couple of weeks ago now. Ashley and I, who have both, we've both been in comms roles at companies, you know, communicating a lot of change, sometimes reductions in force and during COVID. And we're wondering like, oh my gosh, what is it like inside of these companies right now? Not only from an internal comm standpoint, but that really stems from like, what does leadership tell, you know, their employees? Because I think, you know, so much activity that we see on the outside is really around like retention of the best team members and also, you know, attracting the best talent to the company.

19:47And so this week we have Emily Heron joining us. She is now at Rippling. And what is your official role? Because I know you're a pretty cool one, but she is a seasoned people ops leader at some fast growing companies. So So excited for your new role. Yeah. Yeah. I'm HR evangelist at Rippling, which is a hilarious title, candidly. 50 % of my work is internal. I'm working with the go-to-market teams so that they can have a better understanding and framing for like empathy for HR. And then externally working on like building a bit of a community and network for HR leaders who are really interested in what the future of HR looks like, right?

20:28We've got all of these tools, technologies, and changes coming. It's not the status quo, but we also don't need to panic. So how can we have those conversations and like really lean into our own expertise to move forward? So I love it. It's like, yeah, well, what a great role, because I think you really like meet the moment, of course, but it's like you get to actually leverage, you know, all of the experience you've had in your career and talk about like, if you were in this role today, right? Like you deeply understand what the challenges are for everybody sort of in the people function. And Emily, it's so cool because one of the things I've loved about comms, and I think Helen would agree this goes for marketing too, is like you both live inside and outside the bubble of a company.

21:12And I think it helps you bring like a really interesting perspective to the business and help ground people in reality when, you know, like things can get a little crazy inside the reality distortion field of any startup. And so like you are now inside and outside the bubble of the people team. And usually the people team, I guess like there's recruiting. So you have some external touch points, but it is more internal focused. And so I think that's just like fascinating that you get to play this hybrid, like 50 50 role. Yeah. And candidly, one of the best parts is like an H like an HR or a people role is so busy due to purely the aspect of dealing with people.

21:53I have so much more time now to like talk to my peers. And it's been so fun because like, I mean, I know they're all busy, but I'm getting to gather even more like experiences and perspectives, which really is only refining my understanding, but I think is also ultimately really helpful as we're trying to figure out what is going on. Like I get to kind of build that shared perspective across a lot of siloed experiences, quite frankly. I have had the thought so many times of like, oh, my goodness, like, are my comms people okay? And I think that would extend to the people people as well in this moment.

22:33It's a lot of like laugh so you don't cry and like roll your eyes a little bit. I think it's been like, candidly, it's been a really long burnout period for HR folks. Like the pandemic hit and it's kind of been a nonstop barrage of whether you think it's stuff that belongs in the workplace or not, but like a bunch of non-work things coming into the workplace. and you're just not catching a break. As soon as you're like, okay, we did this programming. It's like, well, we're actually thinking about a layoff. And you're like, oh, that was not really where I thought we were going. Yeah. And so it's been a tough time.

23:14Folks are feeling burnt out. I think like, I mean, being online is challenging right now. It's really challenging being inundated with like really extremely different things that are going on globally from like New York Fashion Week to literally bombing. So like all of that is kind of how it feels to be an HR person. And I think folks are really just looking for like the bright light, a small opportunity to take a breath and like really pushing towards like good is like perfect is the enemy of good. Like how can we get to a good outcome? I think that is really what's driving folks. But yeah, people are a little tired.

23:55So like deep pragmatism, like we have been in more idealized states. It felt like the last time I was like in a comms world, a company, I guess I left in the summer of 2021. So I was in like a pre-COVID and COVID phase of Glossier. And I just remember it was the people leader, the legal, our GC and me like just in the trenches constantly and 90 % of my time was focused internally. And I do think we were in this very like, how do we reach this like idealized state of what a company should be? Because employees had so much power. Companies were scrambling to make them happy. I think we all felt this like moral obligation to like build, build like this, like, you know, future state of an internal culture.

24:42but also and one thing I would love to to hear from you because I felt at the time like it became the responsibility of the company to filter all external events for a team like we for a while were doing a like daily newsletter about COVID and then over time that expanded to include the protests and then like a variety of other political and social issues and you know it's it's slowly tapered but since leaving Glossier and the comps profession overall I've had this thought of like what is the job of a company to translate the world for its team and where it kind of landed is actually like the job is probably to create as much like focus as possible and and to sort of narrow the conversation internally while acknowledging that people are grappling with all these crazy external things, but not to take on the role, not for the company to take on the role of like, we're going to tell you how to feel about what's happening in the world.

25:42Because I think that's just like an impossible role to have. And I'm curious if that's where things are and if employees accept that or they still sort of want the guidance of an employer telling them like what's happening and maybe like how to feel about it. So that last point I think is really interesting. the pressure to keep employees informed, I always thought was nuts. Like, that is that part. Yeah, like that is like, not our job. Our job as an employer is to make sure you like, I mean, what it felt like it was for a number of years was make sure you have the space to process these things that are starting to impact your feelings, your experience at work.

26:25I think like, I mean, I have my own thoughts on, you know, if companies have privatized, if healthcare and employment sponsorship and everything is tied to your employment, like there should be some responsibility on the employer to take care of you and make sure those things are giving you more than the bare minimum. But on the other hand, I've talked to so many founders and they're like, I didn't build a company to become a spokesperson on like global politics. Like that's not my goal. And so I do think like right now in a very employ your favorite market, you have like put the blinders on and focus.

27:08And like the way to manage those comms is like hit your mission and your goals really, really hard and like try to acknowledge things without distraction and that is a delicate balance because where does that line end like where are the things you stop acknowledging at a certain point because we can get really granular from international women's day to like right like there are a lot of recognition opportunities but where where is it all of a sudden you've just to your point, Ashley, start cranking out a newsletter. Like that wasn't anyone's job. Well, I mean, actually that, that actually, you guys have both said this, um, this idea of the power previously sitting with the employees.

27:53Like let's, let's double click on that because I think that's important to acknowledge. I think that when you enter the workforce, when you enter tech is actually very, um, relevant to how you think about, um, you know, what is the role of people ops? What is the role of the employer in sort of like your life? And that period, you know, I got to be honest, like I started working in tech in 2008 and it was probably more similar to how it is now because you had the great financial crisis, like people, all the banks fell, right? There were people getting laid off, like their sequence collapsed. Like there were lots of people who were unemployed.

28:32And at Facebook, we actually got a lot of software engineers, you know, who had gone like a more traditional, like banking route and said, let me brush up my CS degree and I'll go, you know, join this software startup. And so I think the power sat more with the employer for like a little bit during that period. And I'm reminded of that now, but to be honest, all the years in between, and there have been many, I feel like the power was with the employees. And what I mean by that is, you know, I think after Facebook went public, VC got really, really big. I think tech got really big and we just had more startups.

29:13Every startup, you know, for a while, like hiring was a vanity metric and talent almost felt like a justification for evaluation, right? Like, you know, Dropbox played this game very well, right? Like it was, it was sort of the, the brain trust and the engineering talent that a company had was, was sort of, you know, equally weighted to the actual tangible like revenue and things like that. And so I think at the time when it was, it was just such a fight to retain, you know, top talent, it was such a fight to recruit top computer science, you know, graduates from top universities, I think that the employees had a lot of power in terms of what they wanted their employer to be for them, right?

30:03And they wanted their CEO to take a stand and to, you know, sort of like be more aligned with their personal values. And I think that I always felt during those periods that like, this is odd. This is interesting, right? This is not what I came into. However, if you were a young person, you know, early in your career, and that's what you came into, and that was like the norm for you, I'm sure now feels insane and dystopian and cruel in some way, you know, like, so it's just like important to acknowledge like these shifts. And I'm so curious, Emily, like when we worked together, I think it was probably one of the heights.

30:43Like I remember the programs we worked together on specifically around like ESGs and, and DEI. And like, it's, you know, I don't think that those programs have gone away, but they're not, they're not front and center the way that they used to be. And I don't know if there are, and I'm asking you this genuine question, you know, because you're inside companies. How do employees even like, you know, put a vote or like try, try to prioritize those programs like how does it work internally I remember how it used to work but it's just sort of like what is the state of like employee resource groups and and all of the things that we used to see yeah I mean Helen like candidly did it ever feel like it was like actually the business was truly invested in these things or almost like you know employees were holding their feet to the flames and so it was a bit of an uphill battle trying to chip away chip away chip away like my recollection was this is hard and we don't really have leadership fully bought in.