What Breaks First, Episode 3: Chris Ramos (Laurel) with Matt Wallaert (Oceans Talent)

[00:00:00] Chris Ramos: I'm Chris Ramos, Chief Strategy and Legal Officer at Laurel. Laurel helps knowledge workers spend less time on administrative work and more time on work that actually creates value that requires human judgment, creativity, while giving knowledge organizations more transparency into how that work actually happens so that they can enable their people to do that.

[00:00:22] Matt Wallaert: Chris, it's so good to see you. How are you?

[00:00:25] Chris Ramos: I'm great. Thank you for having me.

[00:00:28] Matt Wallaert: I'm so excited because, you know, sometimes on a podcast you interview folks you don't know that well, but I know you very well. I'm so excited to talk a little bit about your journey.

[00:00:36] Chris Ramos: Well, I am deeply appreciative that despite knowing me for so long, you were still excited to talk to me. So thank you for the invite.

[00:00:43] Matt Wallaert: I'm still excited. Now, we got to focus on today because you've worn a lot of hats at Laurel over time. Right. These days, you're the sort of chief strategy and legal officer. I think you've always been the chief legal officer. Right. But talk to me about the evolution of your role when Ryan, the founder, pitched you to come on board and do this crazy thing, you left a lucrative career in law to go with this insane person. Like, what was the pitch?

[00:01:07] Chris Ramos: The pitch was come and pave your own path, and I think that's essentially what I've had the opportunity to do. What I'd say is, you know, the title has probably changed a ton. The job at some level has not changed all that much. And I think since the day I joined, the job has really been to marry sort of my my legal skill and acumen and translate that into achieving various business outcomes and what those business outcomes are have changed, where in the organization those problems have lived has changed, where I within the organization to be close to those problems have lived has changed, but I think the heart of it has stayed the same. And that's just been to kind of go where the messy problems are and try to make sense of it as best I can.

[00:01:57] Matt Wallaert: The name of the podcast is What Breaks First, and you sort of alluded to something that breaks, which is in some ways organization broke first, right? The need to sort of shuffle those deck chairs. I remember a very early meeting where we talked about, you know, it's perpetual revolution at a startup. Every six months you have a new org chart. Is that does that feel like the thing that broke first? Like what what really was the first shift for you?

[00:02:21] Chris Ramos: Things are constantly breaking, right? A company scaling from early stage to mid stage. It is an evolution of breakage and fix until the next time something breaks. And there are the things that break sort of internally when you think about, hey, our recruiting motion is broken or some HR process is broken or some finance process is broken. And then there are all the things that live outside of the four corners of your company that start from within, but really live without like, hey, our customer journey, the way we deliver our product, those things have broken. And those things break several times over over the lifespan of a company. And they break in different ways and at different points and to different degrees. But I think scaling a company is all about this sort of process of break, fix, you know, move to the next break, fix, then that thing you fix breaks again because the company has evolved again. That is, at least has been my experience. That's that's kind of the journey.

[00:03:23] Matt Wallaert: And some of that I mean, you talked about the outside walls and certainly Laurel has gone through changes. Those rebrands we talked about those product launches we talked about, you know, from a even a pre the old version and then legal timekeeping and now timekeeping more generally and then sort of productivity based on timekeeping. I mean, it's gone through those product evolutions. If you think internally, you know, you have scaled how many people you got now?

[00:03:46] Chris Ramos: We're approaching 200.

[00:03:48] Matt Wallaert: Right. And so that's a lot of change in not that long ago. I mean, I think two or three years ago when we first started doing some of this stuff, it was 20, 30. That's a lot of people in a short time. What has allowed you guys to scale the internal team the way that you have so effectively?

[00:04:09] Chris Ramos: I think there are the obvious things like bringing on sort of people with experience and help sort of identify the breakages, who recognize the patterns, who understand how to fix the common problems. And then the other thing, which is sort of core to why we are here today, right, is being able to sort of bring on additional help like flex help. And so, you know, one of the we have hired, we have about 6x'd roughly in headcount over the last 18 months. There is a ton of operational, you know, you could support with a person or one or two people doing something part time. You cannot for 30 or 40 people, you cannot do for 150, 180, 200 people. And so one of the things that has helped us, for example, is using Oceans to bring on people like recruiting coordinators, just to help us with the volume of hiring and process and those sorts of things and being able to bring on those additional resources quickly, being able to bring on people who can help, who can sort of slot in right away and like start to add value and reduce that process friction has been huge.

[00:05:17] Matt Wallaert: Yeah, and I think that, you know, you said something as we were chatting, getting ready for this, you and I, that has stuck with me, which is the cost of recruiting disorganization, right? When you're scaling, you know, 6x the headcount in 18 months, you're adding people just literally day to day, week to week. Talk to me a little bit about moving towards a more organized recruiting process and how you think that's enabled your growth.

[00:05:42] Chris Ramos: Recruiting in very early stage before you have a centralized recruiting function, before you have the operational resources, is really distributed amongst the hiring managers, right? And people do everything from sourcing themselves to scheduling themselves, to putting information, if you have an ATS, putting information in the ATS themselves. And that comes with, you know, that comes with a whole host of of problems, like all the problems that you'd assume you had when you've got five or 10 people doing things five or 10 different ways, you know, on five or 10 different timelines and sort of running their own process. It impacts the candidate experience. It impacts speed to close roles. It impacts the quality of candidates you get across the line. It impacts all of those things. And as the company scales and as we're able to bring on more resources to help centralize a lot of like that operational, those operational pieces to bring process discipline, to bring consistency to the candidate experience, to bring repeatability. You're able to, one, give managers, hiring managers who have, you know, there are other elements to their job, like give them the time back.

[00:06:48] Matt Wallaert: I mean, candidate experience affects the quality of talent that you're able to recruit. And so, you know, people are feeling like, you know, at a company like Oceans that roughly doubles in size every year. Right. We've got to double our headcount every year. You know, if you don't get back to somebody, you lose that person. Right. To a better offer, to another offer, to their own sort of the bad taste that's left in their mouth when that happens. I know one of the Oceans folks, Janice, has been able to help out in recruiting. Has that made a difference for you?

[00:07:17] Chris Ramos: I think Janice was honestly one of our first recruiting ops hires, and she was instrumental in helping us get our ATS set up. She's been instrumental in helping us sort of maintain the hygiene of the data and the ATS, she's been critical in bringing some consistency to that candidate experience, making sure that candidates come in, that we're communicating with them, we're keeping them warm, we're moving them through the process, we're scheduling meetings, that people are following up, like all of those things that are really, really critical to a really well-run recruiting process. She was sort of the first instantiation of.

[00:07:52] Matt Wallaert: How have you, you know, we talk a lot about what breaks in the organization, what is broken for you, right? We all go on a journey through this piece. And I know you and your wife and your kids. I mean, you have a family and a growing family. Where have been the inflection points for you where you were like, oh, man, I've got to make some changes?

[00:08:09] Chris Ramos: For myself personally?

[00:08:12] Matt Wallaert: Yeah.

[00:08:12] Chris Ramos: Well, look, at the time that we brought Janice on, I was running, amongst many other things, recruiting all ultimately rolled up into me. So that was breaking for me personally and professionally.

[00:08:22] Matt Wallaert: And it's required different things of you over time as you've grown in the role. So, you know, it's a lot different to follow your friend onto a company and then to be managing a company that's, you know, 6x-ing their worker size in 18 months.

[00:08:36] Chris Ramos: Yeah.

[00:08:37] Matt Wallaert: Talk to me about AI because, of course, you know, Laurel's in the AI space, and so I think sometimes AI companies feel forced in their vernacular to be like, yeah, AI's going to eat everything else and we just won't need people anymore. And right, because that's central to their business model. But it's very much not central to the AI model that is Laurel. Tell me a little bit about Laurel as a product and sort of, you know, the beliefs about AI that the interaction between AI hiring and people that come up for you.

[00:09:04] Chris Ramos: I think the first is that in the technology market today, I think AI very soon will not be a differentiator. Right. Everything is AI And I think for us culturally, you know, we are not a company that leads with AI We want to lead with the humanity, right? Because I think at its core, especially what we do, we're still very human focused. The mission of the company is to return time and not to return time to machines. It's to return time to people like you and me who work behind a machine. The company does that by helping people understand using AI as a tool to help people understand where their work adds value, where it doesn't, direct human focus towards those things that are uniquely human, like judgment, creativity and those sorts of things. And then be able to identify the things that are not and then direct those somewhere else. Right. So that they can be accomplished in some other way. And again, AI can be a tool there. But for us, we really think about the humanity and and try to lead there as opposed with like AI itself.

[00:10:07] Matt Wallaert: There's a little bit of irony about an AI company 6x-ing its human workforce, right? Especially when so many AI companies are like. Yeah, we could do this all with five people and we don't need 6x, you know, talk to me about like you talk about leading with humanity. Talk to me about where that humanity like meets the fact that you are, you know, a technologically first company.

[00:10:29] Chris Ramos: Look, I think I will say relative to ARR and sales motion and all those things, even at a 6x in headcount, it's still relatively small, especially if you look at peer companies, right, companies who are selling strategic enterprise professional services, the company's shape is still very small. As you might imagine, we have an enterprise sales motion. That still requires people, right? Enterprises buy software from people. They don't buy it from a website or and our delivery model is one that's very white glove, right? Again, that human interaction is core to who we are as a company, right, leading with a face that other faces can interact with rather than a chatbot or something like that. And so we still think a lot about like, hey, what are the parts of the company that we want to preserve that feel uniquely human, that feel consistent with the culture that we want to build, both within the organization, but also externally in some areas that requires humans. Now, that doesn't mean that we don't leverage AI to sort of its highest and best use where it makes sense. But again, the mission of the company, the goal of the product is to return time to people and direct them, direct their sort of time, their focus, their energy toward the things that are uniquely human. We believe that there are certain kinds of interactions that are best handled by humans. And so we have humans to do those things. And sometimes that's selling, sometimes that's delivery of the product. It looks different depending on where in the organization you are. AI is great at a lot of things, but that doesn't mean that it's the best it's the best solution to every problem.

[00:11:59] Matt Wallaert: You mentioned culture in there, which I think is always a really important thing. And Laurel, I mean, kind of unique among startups, you have a very, very, very strong company culture, right? You have a very strong group of friends that came together to build this thing. And yet you do work with some external talent partners like us. As you think about one of the things that breaks first is culture. How do you involve outside parties in your culture?

[00:12:20] Chris Ramos: Culture is the lived experience day to day of a set of values. Right. And I think a lot of people sometimes confuse a strong culture with a strong articulation of values. And that's not really what it is. Right. A strong culture is how those values play out in the interactions and in the decisions and in all of the little things that happen day to day. And so the way that the way that we think about culture here within Laurel is something that we were taught by some very smart people is in terms of unique management practices, right, if you want to have a value around, you know, making decisions quickly. Right. So what are some practices that you implement within your organization that are unique and that are directed at making decisions quickly if you have cultural value around this idea of humanity? Right. And human interaction. OK, well, what are some unique management practices that you do in furtherance of that value? Because it isn't enough to just reduce, like put some words on a page and put them on a drive somewhere and give it to people at onboarding and, you know, hope that like it sticks and people live it day to day. You really have to put in place some of these practices to make sure that they're lived in reality.

[00:13:31] Matt Wallaert: Yeah. You said an interesting thing as you and I were prepping that stuck with me was a collective confusion dressed up as collaboration, right, which was a very Laurel cultural thing to say to recognize, hey, we're not living that value of collaboration. It's really just causing churn. How does adding headcount, how does that bringing people in to organize things help align towards a truer value of collaboration?

[00:13:56] Chris Ramos: Look, I think collaboration is one of those things that can get harder the more people you bring in, right, and you collaborate effectively toward some shared goal or business outcome. And I think when it comes to bringing in headcount, the magic is just in being very deliberate, right, about who you hire, how you hire, what you hire to do, how that person will work with other people, because companies are really just collections of people working toward shared goals. And I don't know that there's much more sort of secret sauce than just being very intentional about when you hire a person, like when you hire a person, what is that person hired to do? Are they the right person to do that job? How is that person going to do that job with the other people that are trying to do that job?

[00:14:42] Matt Wallaert: Can we double click on that just for one second? Because when you're growing so fast, there's a little bit of pressure to to lower the bar, right, because you need I need a person. This is the best person I can find in the time that I have. I just got to go. And then you end up making that compromise that you so often regret later where you're like, oh, man, I just if I just held out a little longer and held that bar, that standard that I know as a leadership team. How do you make sure that you're holding that standard while still being able to grow at speed?

[00:15:13] Chris Ramos: I think that the benefits of having worked at a company for this long, for having seen so many different things, is that you learn you get to experience a lot and you do a lot of things wrong and you learn from doing things wrong. One of the things that I have learned that I now believe to my bones is that the wrong person or the wrong role is much worse than no person in that role. But you have to learn that right. And you learn that the hard way by putting the right people in the wrong role or putting the wrong people in the right role. And at the end of the day, what it boils down to is discipline and a shared understanding amongst the people that are making those kinds of decisions, that what we value is having the right people in the right role here. We call that talent density. If you can call it whatever you want. But really what that means is we're very deliberate about who we put in what seat.

[00:16:06] Matt Wallaert: Yeah, that makes a ton of sense as we wrap up. What would you tell an operator who's going through that growth, who's become the single point of failure and is everything is stretched around them and they're stretched and they're not seeing their kids and they're not what's what is what would what is if you could reach out and give them something, give your earlier self something, what would that be?

[00:16:26] Chris Ramos: I'd say that's generally a sign that it's time for whatever the next phase of growth is. There is an inherent tension and intensity in operating early stage companies, that's just the name of the game. But the job is also to not be a single point of failure. Right. And you will be a single point of failure throughout your journey, wherever in the evolution you are. But the job is to constantly be making that not the case. And so I think another thing that I've gotten better at, a lot of it is psychological, a lot of it has been through conversations with people like you, Matt, is it is nice to feel important. And when you're a single point of failure, you can feel very important and that's great. But that is not good for your company. And it is about consistently trying to hire and build your way out of a job. And the great part about early stage companies is that there are tons of jobs and as the company grows, more jobs get created. And I really think about, hey, like, how do I make my current job obsolete so that I can move on to whatever the next job is?