Wade Chambers, Kevin Wang and Wei Gan | Building Company Culture

Hi, everyone, and welcome to today's episode of Gray Matter. I'm pleased to be joined today by Wade Chambers, Kevin Wang, and Wei Gone. We're going to have a fascinating conversation covering company and engineering culture and leadership. Guys, welcome to Gray Matter. I want to start by having the three of you introduce yourselves. And while you work at different companies today, you have a shared similarity in background and lineage. So I'd love if you covered that as part of the introductions before we dive into some interesting topics. Wade, maybe we can start with you.

Hi, I'm Wade Chambers. I'm the Chief Technology Officer and SVP of Engineering at Grand Rounds Health, a company that focuses on improving the quality of care for millions of people throughout the United States and hopefully someday beyond. Been in Silicon Valley since 1994, but have been part of startups from even before then. Oh, and I had the advantage of working with these two gentlemen at a startup called Teleport.

Awesome. Wade, do you want to introduce yourself next?

Yeah. Hey, everyone, I'm Wade Gon. I'm the co founder and CTO of Ribbon Home. And I actually started my career at Telepart, where I had the pleasure of working with and for Kevin and then for Wade when he joined as a VP of engineering and through Teleport's acquisition at Twitter, continued to work with them and then left to start Ribbon in 2017. So Ribbon is a platform for home buyers, agents, and lenders to collaborate on winning cash offers. Our mission is to make homeownership achievable, and we do this by empowering everyday families with the technology and capital that were historically only accessible to the largest institutional investors. And so what we've been able to do is really build this home buying platform with these financial products that really help these everyday buyers make cash offers.

Great. And Kevin.

Hi, everyone. Yeah, my name's Kevin Wang and I'm the VP of Engineering at Abnormal Security. We're a cybersecurity company that protects some of the world's largest enterprises from all forms of cybercrime. Focused a lot on email security to start, and as both Wade and Wei mentioned, I've had the pleasure of working with both of them across a couple different companies, starting with Teleport a couple years back, which was also another Greylock investment back in the day as well. And yeah, just really excited to be here to talk about culture and just all of the stories we've had together building these three very different companies since then.

Great, let's dive in. I want to start with a fundamental, broad question, which Is how do you define culture?

I would love to jump in on that one. There's a very wide variance of how people define culture, but I think that loosely structured, you could say that culture is a single word for the way of life for a group of people and how they interact. And I think this includes the way they do things which are largely shaped by shared experiences, beliefs, behaviors. Done right, you can see culture be a very powerful thing. Just imagine a group of people with shared sort of foundational beliefs leveraging a common way of getting things done, as well as having observable niceties that attract the right group of people to the company. Done poorly, you can see how it works against you and can become a toxic environment where people are focused on things not core to helping the company move forward. And I think that can be the default. You know, people can just take what they've seen done in previous organizations and just try and replicate it in their new role and in their new company. As opposed to decomposing the challenges of your business and getting to first principles and working through the foundational beliefs that need to be shared and sort of figuring out how to work through the transactional way of getting things done and go all the way through it. It's much harder to do that purposefully and consciously. And it requires you to understand the business in a way that you understand what will give you competitive advantage and create true differentiation and then work and probably iterate through the different levels of culture that are required to ensure that culture is appropriate, layered and prioritized for the business that you're building. So when it becomes conscious, it can become this very amazing thing. And when not, it becomes kind of the collection of everything that you've seen at previous companies before.

Yeah, just to maybe pick up that, I felt like it's kind of the difference between what you do versus how you do it and it's more that ladder, how you do things and codifying that in a way that is kind of really felt and really changes how you behave on a day to day basis. Even just thinking through our three backgrounds companies we're at, there's a reason why it's so important in every company universally should care about how you work together. Whether that's a company that's revolutionizing healthcare, empowering home ownership in the country, or stopping cybercrime from enterprises. Right. What we do is gonna be very different based off those technical domains and problems we're solving, yet having a common understanding and a belief and a codification of how we're gonna Work together as this organization. Solving these bigger problems is just critically important for any enterprise and any organization as well.

There's a lot of ways that this often gets summed up in really pithy ways. Right? Culture is what happens when the boss is not in the room. Right? Culture is how decisions get made as well. And I want to echo something that Wade said, which was, you have a culture, whether or not you like the culture, right? There's always going to be some prevailing winds that happen that exist, and how consciously you define it, how intentional you are, really changes. And to Kevin's point, right. At some point, the three of us work together. I would hazard that the kind of the cultures that we've built then, Abnormal Security Ribbon and Grand Rounds, have been quite divergent potentially in some ways. Certainly. I'm sure there's a lot of shared great pieces. But you do have to kind of adapt that from a first principles basis from culture.

One of the things I want to double click on, Wade, I think you mentioned the different levels of culture. Can you expand on that?

I think that there are three levels. The top one, I would say that's what's observable, right? Like, if you had somebody come in and just come in for lunch, like, what is it that they recognize? Well, everybody kind of dresses the same way, or oh, wow, you guys allow profanity on T shirts as you come into the office. Oh, oh, wow, they serve lunch here. There's a lot of things that are just observable, and I think people dismiss it, but that is part of the culture. For example, I've worked at a lot of places where logoware from previous companies was discouraged because they wanted to promote the sense of we and here's who we are. But like, people pick up on that. And so observable, transactional are sort of those unspoken, unconscious rules. For example, is it taboo to be late to a meeting? Do you have icebreakers? It's sort of the lubrication for the organization, right? Like, how do things work in practice? Do you have centralized decision making? Do you have distributed decision making? Do you have functional teams? Or do you have teams based on goals? Like, all of those are sort of the transactional way that you get things done at the deepest level, I think that you get to foundational, and those are sort of the foundational beliefs that your company embraces. Like, what is the core differentiation of your company? How are you actually going to have competitive advantage? Because if you can get it down to that level, then you can make sure that those transactional and observable cultural layers are aligned with that. If, for example, frugality is one of the key differentiators for the company, we're just going to do it cheaper than everyone else. You will probably build systems and culture that helps reinforce that as a point. If quality is the thing that's going to differentiate you, you'll probably pick very different cultural norms to get things done. So I kind of think of things of you cannot violate foundational beliefs if those are core to who you are as a company. The transactional and observable levels of culture should reinforce that and should never run against it. But you kind of need to be clear at which level you're operating at because there will be different changes to the company based on changes that are made.

I want to follow up on that third level, foundational, and connect it to something way said around how, you know there's a difference between being conscious and explicit around defining culture and values and then making sure that gets reinforced throughout the organization. Tactically speaking, you all have been a part of and led teams of varying sizes at varying organizations. What's the best way to actually design those foundational tenants beliefs values?

It can happen in a variety of different ways. I think the more that you can make them conscious, the more that it invites questions and people are able to work through it. So for example, if on a new employee orientation you're able to talk through some of the key things that as a company we believe in and you will see those expressed in like how we do certain things. We will also talk about in terms of company values. We will also celebrate them. The quickest way not to succeed here is to run against sort of these core beliefs that are there. I think the more that there are leaders that sort of walk the talk in accordance with that, it becomes a sort of cultural norm as well. If you know frugality is a thing and you are the CEO, you probably never should be in business class or first class. Right? It's a thing. The more that you can walk the talk and make it explicit, I think that it's there object lessons also become a key part of that. I think if there are sort of shocking rules that can come out right that help reinforce an idea that also can be a very positive way of operationalizing it.

Yeah, just a couple of thoughts I just want to add on to. I totally agree with that, Wade. I feel like I can't remember if I saw this on Twitter, if it was a blog post I read somewhere. But you somewhat had stated if you let Your culture kind of coincidentally codify based off whatever the first 10 employees happen to do for the first X months of the company's journey. It's a very dangerous way of building intentional culture for what you're doing. And I think the takeaway is you have to be very principled of stating up front. I think to everyone's point here, what is the culture we actually care about that will create that differentiated advantage of how we're going to operate that will ultimately let us win as an organization if. If we just treat it as a random kind of chance, that's just risky, right? To what you're doing in the company. And in addition to taking that as a principled kind of measure of what those values should be and thinking about them first class, I also just really believe if you don't have the right rituals and artifacts you're designing into your company's and your team's or organization's operating system, things you're doing on a daily, a weekly, a monthly basis that are working from those actual cultural norms, then has it actually changed the way you're operating on one of those cadences or is it just words on a wiki page or words on a poster or logos on a T shirt type of thing, which is a very empty type of empty, calibrate, empty feeling of culture. And so it's really important just to think through what are those appropriate rituals that are maybe different for engineering than they would be for product and for sales or for marketing. But there's always a way to personalize and embody those values. Values as appropriate, right? Team by team and function by function. And then I think the third one that's I think been a big thing we've really been trying to work on and just kind of test with and iterate over time has been, I think way you mentioned this earlier, is culture something that is seen as a. Almost like in a negative life? Is. Is it the. Is it the stick or is it the carrot?

Right?

Are we both promoting the positive examples where we're holding up people's ideals for culture, where we're going towards from. Or is it see seen more as just don't do these things right in more of a negative antagonistic way? How do you make this become an energy creating discipline for the company versus almost a punitive measure which isn't as thriving or as fruitful as an exercise.

In the creation of culture? I can share a little bit about our journey from the early days and pretty frankly the mistakes that we made along the way. And so one key learning for us was that in about the second year of the business, right, Basically towards the end of the first year of the business, we define a set of five core values. One of the challenges with that was that we didn't define one of the more fundamental pieces, which is that we care a lot about people being mission driven at the company, which means that we didn't interview for that. It was not written anywhere. It was not one of those five core values. But it was clear that the founders acted this way. It's clear that the people who are more successful. And so it kind of permeated the culture anyway. And so last year, we actually had to kind of go back and one, revisit the core values, but realize that there's something more foundational for us that was missing, which is broader ribbon approach that we had created, right? And so this stuff is scary for company leaders to make, right? Because it always feels like you're etching it in stone, right? You cannot kind of go back to the whiteboard and erase. But the reality is that while these foundational beliefs are, they should be as permanent as possible, the reality is that companies grow, right? They, they, they evolve. And you kind of need to continue to evolve along with, with what you're trying to do as a business. Right. Whether your mission grows, right. Whether your customer base changes, right. Whether the market changes, you'll need to adapt to that. And so some of those founding beliefs should never, ever change, right. A lot around the mission, right? But companies actually, I think, do a mixture of discovering what their ideal culture is. Right? So in that sense, you know, I don't want to give ourselves too much flack as well for getting those five core values wrong at the start. But I do think what we've learned is you need to kind of continue to reshape that and create more foundational pieces sometimes on top of core values.

I would just add that I think that's the quickest way to failure is you get so in love with your values or some of the cultural norms that you don't realize they were wrong and go back and correct them. They should be reevaluated and as the market changes or as you find out new things about your business, right? Like those should be one of the things that you are very deliberate about inspecting and changing as appropriate. Kudos for doing so.

I'm actually really curious there. I mean, I would love to hear more of, you know, some of your, both of your stories about what are some of those artifacts you're Using to embody mission drivenness and actually test for that. Right. We're not talking to candidates. But another just question came to me way when you're talking through this evolution, you probably had some type of founder driven conviction. We had to change the core values that maybe was controversial, maybe not well understood or even accepted by everyone on the team. Right. There's kind of this blend of is that a democratic decision you have to do when you're changing the culture that the whole team has embodied? And how do you kind of shock the system to introduce something that's new? Right. In this case, maybe you guys already knew that was one that was an implicit six that just wasn't stated. Maybe it was a bunch of head nodding. Oh, totally get it. Right. We should have just added that one. Or maybe it was a little bit harder to actually roll out. Right. And affect that kind of change. Was that a challenge for you as you went through that?

It was a massive challenge. Right. And all startups have all sorts of challenges, but the kind of the more foundational your fixes are, the more transformative they are for the company. And so this manifested, I'd say very specifically as what we have learned to call proxy battles. And so a proxy battle is when folks are arguing over something, when they actually fundamentally disagree with something bigger under the hood. And this started to happen because there are multiple ways to build a successful company, right. And so the proxy battles were around how missionary versus mercenary. And no one is going out there and say I'm mercenary. Right. But basically how much short term pain are you willing to take as a company knowing that this marches better towards your long term vision, alignment, Right, that's one. And then the other piece that I can go a little bit deeper into is actually how much of a kind of command and control culture do you want to have versus an empowerment culture? So we have taken the path now of empowerment culture. That being said, there's times where you gotta have the command and control culture, right? You know that peacetime wartime question. And sometimes, you know, myself having been in the Singapore military for a while, like sometimes you just need that. Right. And so we've chosen the empowerment route. Right. But it wasn't necessarily codified. And so we found ourselves with proxy battles across, you know, specific leaders across the company in terms of how we made decisions, in terms of like how they worked with their team, in terms of how we're setting goals. Right. And so those things kind of bubbled up and we had to kind of take a step back and realize that the true underlying thing was that, hey, we actually have this disagreement on what the fundamental way is to do that.

Right.

And that needs to get hashed out. And sometimes that results in pretty painful change for the organization. Right. But what comes out on the other end of it is much more alignment. Right. And so now at this point, right, we are going in to every kind of hiring conversation where part of the process is the candidate gets sent the approach document and you can read the approach doc, and there's parts of it you're going to like, there's parts of it you're not going to like. And we can talk about it, but this is the kind of the approach you're signing up for. And it's really important to kind of do that up front because hiring is such a kind of key, key piece of culture.

That's really interesting on the approach doc. I mean, one thing I'm always curious about is everyone talks about culture fit as a key part of the assessment process in the hiring process. How does one actually determine culture fit? It sounds like you all share a document or an artifact around Ribbon's approach and have candidates react to that. That's super interesting. Are there other tactics or ways people do that?

One of our core values is put the patient first. And so as a health tech company, you kind of need to do that. And so if you walk in with a lot of ego, if it's all about you, the chances that you're going to put someone else first is less likely. And so we look for people who are humble, hungry, smart, and we want to make sure that we provide plenty of opportunity for them to showcase themselves and comfortably be able to do so. But the number of times they say I, me versus we and us, we pay attention to that. We also start with some pretty open ended questions of what are you looking for and why? And it's interesting when it's so wide open you get to hear a lot about how a candidate thinks. And so if there is a good fit, we can actually add value to their career. We can help them grow in some way. That's awesome. And that's not necessarily mission driven. Not everybody can be, I believe. But the more that they've been personally impacted by something surrounding healthcare, the more that they lean in and this becomes their job to actually fix it. When they find out that they can impact millions to potentially hundreds of millions of people and actually improve the quality of care, you can see them almost light up and the sort of questions that they ask are fundamentally different. It's no longer about market size or how you're doing and getting traction. It's about the impact that they can make. And it becomes a pretty clear signal that this is someone who's more mission aligned than what's the financial outcome associated with going to this company? I'm curious if there's anything, Kevin, that you see in your company that's for folks that are around using data and analytics to actually find the abnormalities that might exist out there. Is it largely mission driven or is it largely the challenge of being able to solve that sort of technical problem?

Yeah, I mean we, we do have some areas around that. I will say there's, I guess to your specific question, Wade. I'm being data driven. I do feel like I have a distinction between some types of cultural norms that are more teachable versus some that are more intrinsic in nature. Right. I mean, I don't want to necessarily have to penalize a particular person who just happened to be birthed and born out of an organization that wasn't data driven for some reason, even though they have the intrinsic understanding of why that's an important ideal and they can't actually do that over time versus some things are just more core to the way they behave as well. So for that specific question, no, I don't ask someone like, tell me how you, you know the best kind of Excel embedded function you know how to use or whatever to prove to me that you're the most quantified person in the world. But we do care that they are rational, they're logical, they're making decisions in a kind of an empirical way. Right. I will say the other ones, I do feel like that more in that second category. These intrinsics we really care about that I think do permeate across companies and organizations that aren't as multiple. There are some ones that we kind of look for. Right. One for us that we think, think through is we aim to build the most customer obsessed company and team. Right. I think many teams and companies have that aspiration as well. And we really try to drive how are we going to figure that out? Right. And one of the key things and as we adapt through this and iterate we've kind of asked through is one I always feel like our underlying ethos, the thing I try to challenge my teams and myself personally with is when you have a customer dilemma or a customer problem that gets escalated to you, whether that's a bug or, or an incident that you're working through. Our ideal is not just to service the business or satisfy the customer request answer their question and then move on to the next thing. The challenge is to delight the customer in every way, take every moment and make it a delightful moment where you go above and beyond what their expectations might have been. And you can do that even when you're reporting on an incident or trying to get different cause of error, report for why something didn't go well and turn that into hopefully a delightful. So what do we try to do in some of those interview type questions that, you know, we've been talking through? Well, you know, the easiest one I guess we can ask is tell me the time you didn't meet a customer's expectations, what'd you do with it? Right. And for me it's really the, you know, the thumbs up strong. Yes. Over the bar is did you not just service that business? Did you delight the customer, what you kind of went through?

Right.

Versus did you just service that business? Or maybe you didn't. Right. That would be the negative. Right. We're just like anti pattern we want to bring to the company. And then one of the other things I think on those intrinsics here around this customer obsessed mentality that we've also thought there is, if you're happened to be in a role in a company or in school, you're a new grad, you haven't had customers yet. Well, how do we derive that? Right. Well, that same signal we've tried to ask ourselves at the core, we believe for customer obsession, it kind of comes down to empathy at the end of the day, the ability to put yourselves in someone else's shoes and understand as a customer, why do they even want that thing? What are they actually asking you for that we can improve and service or handle for them? So in these types of situations, what we'll frequently do or what I've asked on occasion is tell me at a time you got to apologize to someone, maybe in a professional context. Right. What happened and what was the outcome of that conflict that you kind of went through? And again, what I'm trying to understand there is did you even understand what you were apologizing for? What was the health of the relationship at the end of it? Was it just wash my hands of it and move on to it?

Right.

Or were we able to really, truly understand and reconcile and build a fruitful partnership relationship in the long term as well as one of those kind of bar raising and delightful moments that come out of that? So yeah, we're trying to find ways to intentionally design questions to suss out these types of Signals, some of them more easy for industry veterans who have had customers for a longer time. Others, everyone's had a relationship before and has been in that situation. They've had to apologize and try to be able to assess that a little more. Generally speaking, as well, to Kevin's point.

Some of the time it's not even about asking the right question to find out if somebody is aligned. Sometimes it's about asking the question to find out if somebody is misaligned. One of the things that we've done in the past and when we had somebody who was in a very senior position coming through the interview cycle, is we will actually embed a doctor into the interviewing cycle and have them ask about the Hippocratic oath from the standpoint of software engineering. Right. Like, how are you going to ensure that you do no harm? And it's really interesting to see a candidate sort of go through that cycle of, oh, wow, right. Like, I actually have to think through that. And if you're not excited about both the good that you can create and the need to make sure that you're aware of the potential pitfalls or challenges, then this might not be the best place for you.

I really like how there's so much codification of what the culture is, what the questions are, because I do think that the word cultural fit has a bad rep now. Right. Because it can in its worst case. Right. Has really terrible diversity equity inclusion implications where it's, would you pass the airport test? Right. If you're stuck with this person at the airport, would you want to get a beer with them? Right. And that's kind of the worst manifestation of it. And so I really like what Wade, you and Kevin have described here as trying to codify that as specifically as possible. Right. Because you do need to train the interviewers on it. Right. You do need to make sure that they are specifically looking for some things that are. That they don't come out of the interview. And it's like, oh, did I like them or not? Right. And so I think that's really, really critical. I just want to call that out as kind of a key piece of cultural fit and the kind of the bad stigma around that word, and. And instead really testing for specific pieces that will make them successful within the context of your company.

Yeah. I mean, I think we just have to do that in this kind of intentional way.

Right.

To make sure it's not a loose, warm, fuzzy kind of feeling you're having in a kind of uncontrolled, unsustainable way as well, actually, I'm curious to go back to one thing you were saying earlier way about this proxy battle kind of example you had.

Right.

And I guess my underlying question is how, how do you make that culture of being mission driven seen in this kind of positive light? Maybe that's an easier one. It's a pretty positive statement to say you're mission driven. But certainly I think if you go around whacking people in the head saying stop having proxy battles, you're doing that. You're not a mission driven person. You can kind of poison this very positive thing into just being like a punitive measure you're feeling all the time in the company. I'm curious, are you seeing ways or what are some of those pragmatic tips you have to make sure that culture becomes a positive rallying point, not like an energy sucking type of feeling feeling that you guys are having.

That's a great point. And you don't want it to feel like the carrot more than the stick generally, because if not, it can get really toxic or even the good things can kind of feel toxic if they're, if they're used and if they're kind of weaponized. Right. And so in this case, in the mission driven front, one thing that we do, for example, at every all hands is we celebrate a homeownership story of the week in that we tell the story of, yes, how we met them, including the kind of the growth and go to market story around their product experience. Right. But ultimately, like, what's the story behind this family and this home? And so we tried to pick out the stories that really mean the most to those families. And for example, there was a family that needed to move to a certain school district for their special needs child. And so they needed a certain deadline to get registered in this school district because that school district had the special program for their child. And so they're able to use ribbon to do that. And we try to tell that story in its holistic sense, not just like, hey, we got the deal done. And it's really important because as companies, as all companies grow, right. Certainly grand rounds at a, at a later, later stage than, than abnormal and where ribbon is at right now. But as companies grow, the numbers become large. Right? And we're talking about like tens of thousands, right. Millions of dollars, billions of dollars. Right. The, the kind of, the stories can get lost in the shuffle. And so I do think like codifying that and really reminding folks what each one of those customers means is a really critical part. And we try to codify that in all hands. We try to codify that in onboarding processes and kind of going back to the individual stories and really humanizing it. And then that really is what draws people back to the mission.

Yeah, that's cool. I always feel like whenever we have the chance to get those customer anecdotes back in, to just see are our customers really appreciating and enjoying the product we're bringing into the world has always been just a very energy producing type of moment for us, which is great. I mean, one of the other things I think has been really, really fun for us and I think has been really energy creating the company. Something we started doing probably, I don't know, the last six, six or so months, especially in Covid, where we're not seeing people in the office anymore, where maybe you could see cultural bar raising behaviors just in front of you when you're in meetings, in the hallways, talking to people. Harder to do when you're on zoom, right? You just don't see anyone at all. We've started this practice where every day at the end of the working day, the executive staff gets on a stand down call. We're kind of just going through what happened that last day, just reporting out blockers, that kind of stuff. In addition to that, we're also now saying, can we please call out people who have been doing amazing cultural bar raising behaviors in that past day? And you know, writing down those different examples of Susie's amazing today. She really embodied Velocity, a core value for us at Abnormal. For these reasons. Here's what happened and here's the behavior she did that really exemplified that for us. And then we send these notes out to the whole company every single day. So there's like this steady drip of very kind of inspirational stories of all the amazing work that's happening, right, that's happening across the board for the whole company. I think the way Evan, our CEO, talks about it is we just want to give the team like the cheat codes of what it means to be a bar raiser culturally in the company. You don't have to like make it up or guess anymore. Just read through the daily emails. Just do what Suzy did, right? Find a way to reinterpret that to your function if you're, if that person's in sales and you're in engineering or whatever it is. But these are the things we're celebrating that are giving us a lot of excitement and, you know, energy every single day. And it's really fun. It's kind of a Great highlight of a way to end the day every day. Just kind of reminding ourselves we're surrounded by amazing people that are doing amazing actions and practices on a daily basis as well.

That's awesome. We do something similar in our stand down, but at the end of the week, we go through wins of the week and everyone gets a chance to talk about the impact that they've had or somebody on their team. I think it's a really cool exercise. I also like the idea of in all hands being able to tell stories. It's one thing to sort of toot your own horn, but when you actually have a live video that's walking through a person who you saved their life or impacted them in some significant way, I can only imagine at Ribbon of, where you help somebody buy their first home or their dream home that they've been waiting to get into, that's just incredibly impactful. And each and every time you do that, everybody in the crowd remembers a little and applies it a little bit more deeply.

Those are really powerful examples of how you guys are operationalizing culture and creating rituals to continue reinforcing the company values. I want to go back to something way you touched on briefly, which is how culture relates to creating and growing diverse teams. And I wanted to just open that topic up and ask you all, what do you do from a cultural perspective to ensure that as you scale the organization, you're scaling the organization in a highly diverse and inclusive way?

That's a great question. And I think the key thing for us is that diversity, equity, inclusion became a business, not just a moral imperative on one side of it. It is a talent question, right? How do you make sure that you're attracting the world's best talent? And if you don't have a diverse team, you're looking yourself in the mirror and saying like, hey, are you really then attracting a broad enough group of talent to be able to go after problems? Right. For us, it's also fundamental to the mission, right? Housing and why we started the company. And a lot of the founding story for Shaval, my co founder and I, was around dealing with inequality and sometimes systemic racism and in housing policy in America, right? And so if that's part of the founding story, if that's part of the mission, then it would be hypocritical for us to not have this diversity, equity, inclusion as part of the culture, right? And so what elevated it for us? Right? And it took a while, I'll admit, for us to get to where we are today. And there's obviously A long road to go. But what the kind of. The key flip for us was that it became a business imperative. Right. It cannot just be a moral imperative for the company. And with that, then you can justify the investment, so on and so forth, and really breaking it down for us into diversity, right. Which is how diverse is your team? Like, that's going to show up in metrics, right. And then without inclusion and pay equity. Right. And equity across the board, the diversity is unsustainable. You might be able to have a really strong pipeline. Right. You hired kind of underrepresented team members in. Right. And you kind of build a diverse team across different functions, but without the kind of pay equity piece. Right. Without the inclusion aspects. Right. It tends to all fall apart pretty quickly. And, you know, it's. It's kind of hard and it's a painful thing to see, right. Because you do all this investment up front as well. And so really kind of splitting it up into those three pieces. I'd love to hear from Wade or Kevin, like, what you've done with your teams to really help push this forward.

Much like yours way, we have a genuine business problem, right. And healthcare doesn't just apply for, you know, white males. Matter of fact, the majority of healthcare decisions are made by females in different geographies of different ethnicities. And so. Right. Like you have to have products and services that reflect your users. And so we've done a few things. One is, I believe it's hard to bring the exact talent that you want to San Francisco. So instead we want to take our roles to where the talent is. And so we are actively looking for talent in different geographies that make up the ethnicity and the gender that we're looking for that come from great schools that have great capabilities. We need to find them where they're at, not assume that we're going to be able to bring them to the local market. Also, I would say that in attracting a lot of the right talent, they need to see themselves in their leadership. And so the more that you can have in positions of power, the type of person that you're trying to attract, I think the better that you're going to have. So constantly looking for, you know, who is that next leader and can I find the next great leader in Atlanta, Georgia? And how amazing is she going to be? And is she going to be able to stand up on a pedestal that will attract more people to us and how can I help promote that? And so constantly thinking about where I can find the talent that we want and making sure that they reflect our user base, I think just shortcuts the whole process for getting the product that we want in market.

I think for us, this has been a. It's been a struggle. I think it's one where we're still trying to figure out to be. To be totally honest and trying to adapt into. I would say, you know, in some ways it's kind of ironic. I feel like when we talk about culture and taking it so importantly, we're actually saying there are some things that we want to have diversity on. You have to embody these cultural norms, and yet we have to pick the right cultural norms that have a diverse applicability to a lot of different people that are across ethnicities, genders, et cetera, on that side. So it's kind of like we're actually diverse in some ways, but not diverse in others. It's actually what you mean when you're saying we are emphasizing and creating a codifying culture internally. Secondly, I would say, certainly, Wade, to your point. The teams I think that have been most successful with building diverse teams here are ones where we've been able to prove and to show leadership is, you know, coming from not an Asian male background like myself, they're embodying these core values of the company we have. And when they've been empowered and been bet on and thriving their careers, they've been able to build the most diverse teams around them as well, because they see that the company's, you know, putting their money where their mouth is kind of, so to speak, in that. In that kind of dimension. So I do feel like it really is coming up with the right cultural values that you're not trying to compromise on and actually being homogenous, there's. And yet they have to manifest and be appropriate and attractive.

Right.

To a broad swath of people you're actually trying to recruit into the company as a whole. And hopefully by doing that, you can be a empathetic and a relational person that a broad right of people can relate to as well, even if they come from very diverse backgrounds for yourself, because they realize we're actually very consistent and very similar across these cultural norms at the same time, even though these, you know, we do have background differences there as well.

That's a great point. I think, for us, what you all mentioned around the team being able to see themselves in leadership. Right. So when we hired Sarah Walker, who's our VP of engineering, a few of the female engineers on the team came to me and said, like, thank you for running A process that was inclusive enough such that we found the best candidate that was female. Right. And they mentioned the words possibility model to me, right. And I really had to kind of understand the depth of that and the value of that after the fact, which has helped us really kind of build out diversity across the whole leadership team, right. And then diversity across the company. And there's so many kind of different dimensions to talk to this about. But I'll offer a little bit on the inclusion and equity front, right? Because that's the, that's kind of the sustainable part of the culture. And I do think there, there tends to be more literature out there on the how do you source diverse candidates, right. How do you kind of make sure that you're tapping a wide enough pool? I think on the inclusion front, one thing that's interesting about this kind of zoom world that we live in, right, Is that it's harder to naturally hold inclusive meetings. There's a little bit of lag on zoom. And so it's easy to cut each other off, right. And it's easy to kind of, without thinking about it, really just dominate the conversation. And then one thing we tried at the start is this concept of silent meetings. And so silent meeting, we didn't come up with this. I know Square and Amazon do it kind of the meeting leader comes in with a document and for the first 10 or 15 minutes or so, everyone's reading document, writing comments in there. And then only after that, right, do we kind of open up for discussion. And that meeting leader facilitates based on all the comments in the doc. The first thing we noticed with this is like there's dramatically higher throughput, right? Just from an engineering point of view, this is how, this is how we think as engineering leaders, right? Just more throughput, more ideas coming out. And the second one was that we surfaced a lot of ideas from people who were generally more introverted and quiet. That was kind of a wake up call for us, right, Is in that we weren't necessarily always surfacing the best idea because we didn't have the kind of fundamental mechanism to run the meetings on this front, right? So that's one on the inclusion side that I think was just a really helpful piece for us. And then on the equity side, one thing that we've done a little bit earlier than I think a lot of companies at our stage is really start to codify structure and pay equity with levels. And this tends to be more codified the later the company is. It was a tricky thing for us to decide on doing Because a lot of startups shun away from structure and process at this stage, right. And one, fundamentally from there's just a lot more to do. Right. And then, then two, you do want some amount of flexibility and that is the value of an early stage startup. And so we try to introduce kind of just enough here so that the fairness is paramount. Right. And the more fair the system, basically you kind of create more powerful incentives. Right. Why should people feel like they're getting promoted? How does the rest of the team feel? That's fair as well. And then the more transparent you are, then the kind of, the more the team feels there, there's kind of equity across the board, right. Where they're not having to lobby for it, right. You just kind of heads down, you work hard, right. And you get, and you get, you get paid more. You know, your career grows. And I certainly had the benefit of that working with and for Kevin and Wade. Right. And so trying to kind of codify that, that part of the culture to make sure that the team really feels like there's equity in place. So can just be heads down, do their best work and good things will happen.

Those are excellent points, Wei. I want to transition to maybe one final topic which I'd be remiss not to hit on given the three of you we have on the podcast. The three of you lead in specific product engineering technology teams. And one thing I'm curious about is how is culture different in an engineering and product development context versus a company wide context? Where is it in alignment? Where do you all see some conflict get created?

Ultimately, every team has to translate culture or objectives as appropriate for the overall teams and functions. I can just go through maybe two different versions of two of our cultural ideals and some of the things we're doing on the engineering side to embody them. One I've already mentioned slightly early in this conversation around Velocity, we really pride ourselves a company that has extremely high velocity. We care about being good today is better than being perfect tomorrow. Let's just make that constant cadence of daily progress one of the days we actually have. I'm sure both Wade and Wei will remember some of this just from our shared past histories. One of the most important ways I think we codify this literally on day one is we tell every engineer who joins the team you're expected to ship code by the end of your first day. Now we never are giving someone the gnarliest biz logic bug to fix the most complex problem no one else has actually figured out. Usually it's to be honest, a little more of a ceremonial type of change, a one line fix, add a new metric to instrument that gives us some more visibility to the stack, something more minor that nature. Because the reason we're doing that is not because we care about adding business value from day one. It's the cultural statement that this is what good today is better than perfect tomorrow. And we've actually had to tweak some of our onboarding practices to move some of the onboarding talks we normally did on day one to later in week one or in week two or in month one to free up time on day one to actually ship code. So that's probably different than someone on the sales team or whatnot who's not going to close a customer on day one. Right. You probably couldn't do that unless you were enabled to know what the sales pitch is, what the pricing is, et cetera. But we can manifest that differently across engineering as one example. And then another example that comes to mind for me is we think a lot about ownership as well. Right. And for me, the way I've really tried to think about that with my teams has been if us as engineers, the only reason we take any action we do the work we're doing this Sprint or this day is because a PM put it on the roadmap and we ultimately like, you know, pulled it into the Sprint or a bug was raised by a customer and we ended up having to go fix it. Are you actually being an excellent owner of your engineering systems? Right. Because ideally if you're an excellent owner, you are in so much mastery and understanding of your systems, you're proactively getting ahead of those problems before they're reported to you by customers as well. So one of the things we've really started building out is some of that operational discipline into the team where literally every Monday morning the first things that all the teams do is they go through operational metrics, check ins to say top to bottom, here's the SLAs or the different metrics that quantify system or product health. Report them out to see any norms or variances from previous weeks and say based off what we've seen, we need to take action on these, even though they haven't been reported by a customer or anyone through any kind of escalation. Now it's possible that sometimes we'll say we're not going to take action on these based off of prioritization. That's fine, that's what prioritization means in the day. But I really want to make sure that the teams are doing that in a very intentional way. That's an explicit depriorization versus one that was just not even realized or recognized as well. So does that ownership model look differently for a sales or a marketing person? Probably, but that's just one of the ways we've tried to manifest that personally for engineering, at least for these two different core values.

I would say that from the grand rounds health side, I think that we have a very diverse in both geographies and also in the types of roles that we have inside of the company as well. And so when you are dealing with a patient, everything is an instance of one. Right. And like every case matters and everything has to be dealt with that is specific to that episode of care and like helping a member move through it. When you get on the EPD side, you have to be very concerned about the instances of. But you have to be able to connect them to classes of problems. And so the ability to zoom out and understand the abstraction that it fits in and then to be able to prioritize against different areas becomes something that's very unique to the EPD organization where it may not be as broad in its application. I think that ability to make expected value calculations of understanding the upside and the probability of hitting it versus the downside and the potential probability of that as well is something you have to constantly be triaging between different things that you can do so that you're constantly selecting the thing that is going to have the most business impact. And oftentimes that's something that's very specific to EPD as well in sharing product and design.

It's a great question on the kind of company culture versus team culture. Right. Because similar to what Wade said, it really resonated with me. We also have a lot of different functions at the company. Real estate operations. Even within real estate operations, there's underwriting of homes, underwriting of buyers. And so that kind of diversity of functions means there's a lot of different teams across the company. I think the challenge for leaders of functions. Functions, Right. Functional leaders, if you're. If you're ownership of a specific team in the company, is to not try and create a strong culture by making it a us versus them, an exclusive culture where you are basically creating common enemies outside your team. And that is a easy trap to fall into because it's an easy rallying cry. Right. Where a lot of fintech companies see this. Right. That we've had to really check ourselves against is this growth versus versus risk. Right. Often lies in different functions, right? Oh, risk is not in the way. That's why we're not hitting our deal target. Oh, we're doing bad deals. We're taking on too much risk. And that's kind of a natural tension that'll arise. And it's really important for those leaders of those functions to make sure that no, we are on the same team and kind of make sure it's always laddered up. And so I do think though that like strong cultures are not only created through that means, they're created through other means as well around shared rituals that to what Kevin's and Wade's examples are, that may be different for an engineering team versus a sales team. And where Ribbon specifically tries to put this in practice, we've actually tried some versions of like different principles or different like core values for the teams. Right. What we've always gone back to is actually translating the company core values. Right. So now we have three core values at the company level and then translating that from the company to the team level level. So as a specific example, one of the company core values is set new standards. Right. Really pushing the bar on innovation at the company level that might be improving a certain process. Right. So that we can close on a home even faster. But on the engineering team, then that gets into the kind of technical world of where we used Amazon Textract. Right. They're kind of OCR and kind of document parsing tools before while I was still in beta stage. Right. And kind of took the requisite risk on that. But it did align with our core values because we were able to deliver something to the market that wasn't broadly available to any kind of competitive set in the space. And so I do think in the same way, companies are pretty good at doing this on the okr basis.

Right?

Company sets company level, okrs team set theirs in turn. Right. I do think a similar pattern can be done on the culture basis as well.

Yeah. It just reminds me of one thing I did which was a fun exercise probably over two years ago now when I first joined the company that has still been very durable to this date is I just spent an afternoon try to write a one page essay on what I called Good Engineer, Bad Engineer. It was inspired by Ben Horace's very famous blog post on Good pm, Bad pm, which just basically personalized all of our core values at the corporate level to personalize us and interpret them. What it meant on an engineering level as well and was kind of intentionally hyperbolic. Not meant to judge someone as being Morally bad as an engineer if you don't do any of these things and you violate these kind of practices, but more as an aspirational kind of statement of what we should all be trying to do a little more of every single day. And it's been really fun for me to have to write down my thoughts that way and also have it as a conversation starter with other engineers. Right. Just what are your beliefs and practices as engineering leader, as an engineering developer and kind of swap stories and understand are we really aligned to what we're trying to build? And just even on a personal level, we're trying to aspire to get better at our own crafts as well. So I think that personalization was a really fun and fruitful exercise for myself as well.

Wade and Kevin, what are some of the more controversial. Right. Or the core values that you all have defined? Right. Where the opposite of them has to be just as reasonable. Right. Because we all try and shy away from core values that don't mean anything like the opposite of integrity. Probably not something a company wants to have. But how do you define core values with the kind of the right level of detail and context such that the team understands what some of those trade offs are.

One of the things that we've done at grand rounds, as an example, is on the EPD side we have three principles and we've set them up as X over Y and that we really value Y. But to make it a little bit sharper edged is we are actually introducing X. And the first one is impact over progress. We love progress. Right. We want everything to make progress, but we should never make progress at the cost of impact. If you know something's going to fail, raise your hand if you know that there's a better answer out there or there's something that's even more valuable to the company. It's your job, it's your obligation to stick up your hand and say, wait a minute, isn't this a better way of doing it? Because we value impact over progress. The second one is we over me. Actually, I want everybody to grow. I want everyone to focus on themselves and what's necessary for them to move to the next level. It should just never come at the cost of the team. And so if you ever have a decision to make of whether it's moving your own career forward or like helping the team succeed, I hope you will think about making the team succeed first and knowing that they will also have your back and help you move forward in your career as well. And the last one is Applied intelligence over knowledge. Lots of people like being smart. They just like talking about things and they love pontificating about theory X versus theory Y. I like smart people, I like having conversations with them. But I way, way, way, way more value someone who can actually take that knowledge and do something with it. Can you apply your knowledge to actually actively solving a problem that's directly in front of us? And if so, we value that way more than the knowledge that you have. So like those are three examples of where we've tried to create greater contrast between going through the motions versus here's something that actually creates company value.

Yeah, I mean the one I can add on top of that too is, you know, when we go through, we talk about culture with candidates that are coming in or interviewing for the company, we actually always talk through, here's the core values and all these, the positive lights of what these values embody. We also are very explicit for every single one. Here's like the double edged sword of what they also mean. So like be ready and fully aware of. We're accepting that these are the flaws and words we're going to take along the way because we're prioritizing A over B. Right. So for example, when we talk about velocity, we say these are the benefits we'll get from saying good today, perfect tomorrow. Right. But the double edged sword is we're going to make more mistakes. We might have duplicated work across different functions because we're not checking in on a centralized command and control structure. If those things frustrate you, you don't want to do that, this is the wrong place for you. Right. As one example or one of our other core values, is this ambition for excellence. Right. Are we all getting better 1% every day along the way? And there's an expectation explicitly that we all have to have growth mindset, expecting we're improving every single day. And if we don't want to be in a place where there's growth that's stretching you and it's going to be uncomfortable, this is not the right place for you. And what I tell candidates personally is I hope I'm the right leader for this company in engineering today. I'm sure Evan, the CEO is not confident I'm the right leader for engineering. A year out from now, it's on me to kind of prove to myself and the company that I'll be growing and adapting to the challenges that are coming up in the next year year to kind of re earn this job every single day. Now for some people that's a very menacing, threatening statement to make. Right. You're on notice all the time. For others, that's a inspiring statement because, well, aren't we all trying to get better? Right. And wanting to say, yeah, if I'm not better a year off now than I am today as a professional, as a human being, something wrong has actually happened. Not everyone's going to align with that one. But, you know, I do try to be very explicit of frank about this is what those norms mean for us, and also acknowledging here's the discomfort it might cause some people, but this might actually be a very bad place for you if you don't actually stand behind these statements and that kind of controversy.

Kevin Wade Way, I want to thank you for joining us in this excellent conversation on defining, operationalizing and reinforcing culture. I'm really glad we got to have the three of you here together on Gray matter. Thank you.

Thanks for having us.

Yeah, thanks so much. Really fun and just glad to be able to spend some time talking about this really important topic.

Thanks.

Thank you, Sam.