What defines a company’s culture? Moreover, what are the elements of culture that can make or break the working relationships of a company’s team members? How can startup leaders ensure they are establishing the right culture at the earliest possible stages, and that they are subsequently upholding those foundational values as the company grows?

“Done right, you can see culture is a very powerful thing. Just imagine a group of people with shared foundational beliefs leveraging a common way of getting things done,” says Wade Chambers, Chief Technology Officer and SVP of engineering at Grand Rounds Health. “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.”

Chambers recently sat down with Kevin Wang, who is the VP of engineering at Abnormal Security, Wei Gan, the co-founder and CTO of Ribbon Home, and Greylock partner Saam Motamedi on the Greymatter podcast to discuss the wide-ranging topic. During the conversation, the four talked about the different ways they define culture; how they apply company-level cultural norms to individual teams; how culture impacts engineering teams versus others; how company culture influences what they look for in candidates; and more.

You can listen to the podcast here.

Episode Transcript

Saam Motamedi:
Hi everyone, and welcome to today’s episode of Greymatter. I’m pleased to be joined today by Wade Chambers, Kevin Wang, and Wei Gan. We’re going to have a fascinating conversation covering company and engineering culture and leadership.

Guys, welcome to Greymatter. I want to start by having the three of you introduce yourselves. While you work at different companies today, you have a shared similarity and backgrounds and lineage. So I’d love it if you covered that as part of the introductions before we dive into some interesting topics.

Wade, maybe we can start with you.

Wade Chambers:
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. I’ve been in Silicon Valley since 1994, but I’ve been part of startups from even before then. Oh, and I had the advantage of working with these two gentlemen at a startup called TellApart.

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

Wei Gan:
Yeah. Hey everyone. I’m Wei Gan. I’m the co-founder and CTO of Ribbon Home. I actually started my career at TellApart, where I had the pleasure of working with and for Kevin, and then for Wade when he joined as the VP of engineering and through TellApart’s acquisition by Twitter. I continued to work with them until I left to start Ribbon in 2017.

Ribbon is a platform for homebuyers, 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. 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?

Kevin Wang:
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 cyber crime, 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 of different companies, starting with TellApart a couple of years back, which was also another Greylock investment back in the day as well. And yeah, 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. I think culture is one of those things where 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. I think that can be the default. 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 on that, I feel like it’s kind of the difference between what you do versus how you do it. It’s more that latter 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 and the companies we’re at, there’s a reason why it’s so important to every company, universally. You should care about how you work together, whether that’s a company that’s revolutionizing healthcare, empowering home ownership in the country, or stopping cyber crime from enterprises. What we do is going to be very different, based off of those technical domains and problems we’re solving, yet having a common understanding and a belief and a codification of how we’re going to work together as this organization, solving these bigger problems is just critically important for any enterprise and any organization as well.

Yeah. I think there’s a lot of ways that this often gets summed up in really pithy ways. Culture is what happens when the boss is not in the room. 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. 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, now that at some point the three of us worked together, I would hazard that the kind of the cultures that we’ve built then in 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 to spaces 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?

Yeah. It’s a great point.

I think that there are three levels. The top one is what’s observable. Like if you had somebody come in and just come in for lunch, 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 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 logo wear from previous companies was discouraged because they wanted to promote the sense of “We,” and “Here’s Who We Are.” But people pick up on that. It’s so observable.

The next level is transactional. 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. 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? All of those are the transactional ways that you get things done.

At the deepest level, you get to the foundation. Those are the foundational beliefs that your company embraces. 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.

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 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 of foundational and connect it to something Wei said around how 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 tenets, 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. 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 how we do certain things, we will also talk about it 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 frugality is a thing and you are the CEO, you probably never should be in business class or first class. It’s a thing. And 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 that help reinforce an idea, that also can be a very positive way of operationalizing it.

Yeah. Just a couple of thoughts I want to add on to. I totally agree with that, Wade. I can’t remember if I saw this on Twitter, if it was a blog post I read somewhere, but someone had stated, If you let your culture kind of coincidentally codify based off of 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. I think the takeaway is you have to be very principled at stating upfront, 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 we just treat it as a random kind of chance, that’s just risky to what you’re doing in the company.

And in addition to taking that as a principled 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 companies and your teams 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 calibrate, empty feeling of culture.

So it’s a really important thing 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 as appropriate team by team and function by function.

I think the third one that’s been a big thing we’ve really been trying to work on and test with and iterate over time has been this question of whether culture is something that is seen as almost in a negative light. Is it the stick or is it the carrot? Are we both promoting positive examples where we’re holding up people’s ideals for a culture where we’re going towards, or is it seen more as just don’t do these things in more of a negative antagonistic way? How do you make this become an energy creating discipline for the company? It’s that versus an almost 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.

One key learning for us was that in about the second year of the business, basically towards the end of the first year of the business, we defined 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 was clear that the people who were more successful [acted this way], so it kind of permeated the culture anyway.

And so last year we actually had to go back and, one, revisit the core values, but realize that there’s something more foundational for us that was missing – which is the broader Ribbon approach that we had created.

And so this stuff is scary for company leaders to make, because it always feels like you’re actually getting stoned. You cannot go back to the whiteboard and erase. But the reality is that while these foundational core beliefs, truly, should be as permanent as possible, the reality is that companies grow. They evolve and you need to continue to evolve along with what you’re trying to do as a business. Whether your mission grows, whether your customer base changes, whether the market changes, you’ll need to adapt to that.

And so some of those founding beliefs should never ever change a lot around the mission. But companies actually do a mixture of discovering what their ideal culture is. And so in that sense, I don’t want to give ourselves too much flack as well for getting those five core values around at the start, but I do think what we’ve learned is needing to 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 if 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 re-evaluated as the market changes or as you find out new things about your business. 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 would love to hear more of your stories about some of those artifacts you’re using to embody mission-driven this and actually test for that, when you’re talking to candidates.

But another question from me, Wei, is when you’re talking through this evolution, you probably had some type of a founder-driven conviction, where you had to change the core values that maybe was controversial, maybe not well understood or even accepted by everyone on the team. 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? How do you kind of shock the system to introduce something that’s new?

In this case, maybe you guys already knew that was one that was an implicit sixth core value that just wasn’t stated. Maybe it was a bunch of head nodding. “Oh, totally get it. We should have just added that one.” Or maybe it was a little bit harder to actually roll out and effect the kind of change. Was that a challenge for you?

Well, it was a massive challenge. All startups have all sorts of challenges. But the more foundational your fixes are, the more transformative they are for the company.

So this manifested, I would 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. And so the proxy battles were, one, around how things were missionary versus mercenary. And no one is going out there and saying, “I’m mercenary.” But basically, How much short-term pain are you willing to take as a company, knowing that this march is better towards your long-term vision alignment? 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? That is not to say, “So we have taken the path now of empowerment culture.” That being said, there’s times where you’ve got to have a command and control culture. That peace time/war time question. And sometimes (myself having been in the Singapore military for a while), you just need that. And so we’ve chosen the empowerment route. But it wasn’t necessarily codified.

And so we found ourselves with proxy battles between specific leaders across the company in terms of how we made decisions, in terms of how they worked with their team, in terms of how we’re setting goals. And so those things kind of bubbled up and we had to 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.” And that needs to get hashed out. And sometimes that results in pretty painful changes for the organization. But what comes out on the other end of it is much more alignment.

And so now at this point, we are going to go into every hiring conversation where a part of the process is the candidate gets sent the approach doc. And you can read the approach doc and there’s parts of it you’re going to like, there’s part of it you’re not going to like, and we can talk about it. But this is the approach you’re signing up for. And it’s really important to do that upfront because hiring is such a kind of key piece of the culture.

That’s really interesting on the approach doc. 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. Are there other ways how one actually determines culture fit? It sounds like you all share a document or an artifact around Ribbon’s approach and have candidates to react to that. That’s super interesting. Are there other tactics or ways people do that?

I know for us, one of our core values is to 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 opportunities for them to showcase themselves and to be comfortably 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? 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 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 they are focused on something like 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, we do have some areas around that. Specific to your question, Wade, on 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. I don’t want to necessarily have to penalize a particular person that just happen 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 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 them. I’m like, “Tell me the best kind of Excel-embedded functionality you use, or whatever to prove to me that you’re the most qualified person in the world.” But we do care that they are rational, they’re logical, they’re making decisions in a kind of empirical way.

I will say the other ones I do feel they’re unborn. The second category, that is intrinsic, to really care about does permeate across companies and organizations. that aren’t as moldable. There are some ones that we try to look for. One for us that we aim to build the most customer-obsessed company and team. I think many teams and companies have that aspiration as well. We really try to drive, How are we going to figure that out?

One of the key things, as we adapt through this and iterate, is one that I always feel is our underlying ethos. I try to challenge my teams and myself personally with this. When you have a customer dilemma or a customer problem that gets escalated to you, whether that’s a bug or an incident that you’re working through, our ideal is not just to service the business or satisfy the customer request, answer the question and then move on to the next thing. The challenge is to delight the customer every way. Take every moment and make it a delightful moment where you go above and beyond what their expectations might have been. You can do that even when you’re reporting on an incident or trying to get to the cause of error for why something didn’t go well, and turn that into, hopefully, a delightful moment.

So what do we try to do in some of those interview-type questions that we’ve been talking through? Well, the easiest one, I guess, we can ask is Tell me the time you didn’t meet a customer’s expectations, what did you do with it? And for me, it’s really the thumbs-up, strong “Yes!”, over the bar is, Did you not just service that business, did you delight the customer when you kind of went through, versus did you just service that business? Or maybe you didn’t. That would be the negative. We’re just like, This is the anti-part of who we want to bring to the company.

One of the other things I think about those intrinsics here is around this customer-obsessed mentality. We’ve also thought, If you happen 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? Well, that same signal. We’ve tried to ask ourselves, At the core, we believe in our 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 a time you had to apologize to someone, maybe in a professional context. What happened and what was the outcome of that conflict that you kind of went through?” And I think what I’m trying to understand 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 “I’ll wash my hands of it and move on,” or were you able to really truly understand and reconcile and build a fruitful partnership or relationship in the long-term as well as one of those kinds 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 are 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, how 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 lying. 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. 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. 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 because it can – in its worst case – have really terrible diversity, equity, and inclusion implications. It’s situations like, Would you pass the airport test if you’re stuck with this person at the airport? Or, Would you want to get a beer with them? 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, because you do need to train the interviewers on it. Do you need to make sure that they are specifically looking for some things so that they don’t come out of the interview and it’s like, “Oh, did I like them or not?” 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 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 intentional way to make sure it’s not a loose, warm, fuzzy kind of feeling you’re having in a kind of uncontrolled or unsustainable way as well.

Actually, I’m curious to go back to something you were saying earlier, Wei, about this proxy battle example you had. 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 you could go around whacking people on the heads 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 being this punitive measure feeling all the time in the company.

I’m curious, what are some of those pragmatic tips you have to make sure that culture becomes the positive rallying point, not an energy-sucking type of a feeling?

Yeah, that’s a great point. And you do 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 kind of weaponized.

In this case, on the mission-driven front, one thing 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. But ultimately, what’s the story behind this family and this home? And so we try to pick out the stories that really mean the most to those families. 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 a special program for the child. And so they were 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 our companies grow – certainly Grand Rounds is at a later stage than Abnormal and where Ribbon is at right now – but as companies grow, the numbers become large. We’re talking about tens of thousands, millions of dollars, billions of dollars. Those kinds of stories can get lost in the shuffle. And so I do think 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 we keep 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 – just to see where our customers are really appreciating and enjoying the product we’re bringing into the world – it has always been a very energy-producing type of moment for us, which is great.

One of the other things I think has been really, really fun for us – and I think has been really energy creating in the company, something we started doing probably, I don’t know, in the last six or seven months, especially in Covid where we’re not seeing people in the office anymore. but 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. 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 going through what happened the last day, just reporting out blockers, that kind of stuff. And in addition to that, we’re also now saying, “Can we please call up people who have been doing amazing cultural bar-raising behaviors in that past day.” And then writing down those different examples of, “Susie is 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 this steady drip of very inspirational stories of all the amazing work that’s happening across the board for the whole company.

The way Evan, our CEO, talks about it is We just want to give the team the cheat codes of what it means to be a bar-raiser, culturally in the company. You don’t have tomake it up or guess anymore. Just read through the daily emails or just do what Susie did. Find a way to re-interpret that to your function if that person is in sales and you’re in engineering, or whatever it is. But these are the things that we’re celebrating that are giving us a lot of excitement and energy every single day.

It’s really fun, it’s a great highlight of a way to end the day every day. Just reminding ourselves we’re surrounded by amazing people that are doing amazing actions and practices on a daily basis as well.

Yeah, 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 an 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, Wei, you touched on briefly, which is how culturally [specific] it is to create and grow diverse teams. I wanted to just open that topic up and ask you all what 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?

Yeah, that’s a great question. I think the key thing for us is that diversity, equity and inclusion became a business, not just a moral imperative. On one side of it, it is a talent question. How do you make sure that you’re attracting the world’s best talent? And if you don’t have a diverse team, you should be looking at 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?”

And then from the other side of it, for us, it’s also fundamental to the mission of housing and why we started the company. A lot of the founding story for Shaival, my co-founder, and I was around dealing with inequality – and sometimes systemic racism – in housing policy in America.

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. And so what elevated it for us – 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) – the key flip for us was that it became a business imperative. It cannot just be a moral imperative for the company. And with that, then you can justify the investment, so on and so forth.

Really breaking it down for us into diversity was seeing how diverse your team is. That’s going to show up in metrics. And then without inclusion and pay equity, and equity across the board, the diversity is unsustainable. You might be able to have a really strong pipeline where you hire kind of underrepresented team members in, and you kind of build a diverse team across different functions, but without the kind of pay equity piece, without the inclusion aspects, it tends to all fall apart pretty quickly. It’s kind of hard and it’s a painful thing to see because you do all this investment upfront as well. And so it’s really kind of splitting it up into those three pieces.

I’d love to hear some from Wade or Kevin, like what you’ve done with your teams to really help push this forward.

Yeah. Much like yours, Wei, we have a genuine business problem. Healthcare doesn’t just apply for white males. Matter of fact, the majority of healthcare decisions are made by females in different geographies of different ethnicities. And so 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 leaders. 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 [chances of attracting talent] you’re going to have. So we’re constantly looking for, Who is that next leader and can I find? Who is 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?

Constantly thinking about where I can find the talent that we want, and making sure that they reflect our user base just shortcuts the whole process for getting the product that we want in the market.

Yeah. I mean, I think for us it’s been a struggle. I think it’s one where we’re still trying to figure out, to be totally honest, and trying to adapt into. I would say in some ways it’s kind of ironic. I feel like when we talk about culture and the idea of taking it so seriously, we’re actually saying there are some things that we don’t 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 unlike that (for us and others) is that actually what you mean when you’re saying we’re emphasizing and creating a codified culture internally.

Secondly, I would say, certainly Wei, 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 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 are thriving in their careers, they’ve been able to build the most diverse teams around them as well because they see that the company is putting their money where their mouth, so to speak in that kind of dimension.

So I do feel like it really is coming out with the right cultural values that you’re not trying to compromise on and actually being homogenous there. And yet they have to manifest and be appropriate and attractive 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 an empathetic and a relational enough person that a broad range of people can relate to as well, even if they come from very diverse backgrounds themself. They realize, We’re actually very consistent and very similar across these cultural norms at the same time, even though we do have background differences there as well.

That’s a great point. I think for us, we experienced what you all mentioned around the team being able to see themselves in leadership when we hired Sarah Walker, who’s our VP of engineering. She’s one of a few of the female engineers on the team. She came to me and said, “Thank you for running a process that was inclusive enough such that we found the best candidate that was female.” They invested in the worst possibility model to me 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 and then diversity across the company.

There’s so many kinds of different dimensions to talk through this about, but I’ll offer a little bit on the inclusion and equity front, because that’s the sustainable part of the culture and I do think there tends to be more literature out there on how you source diverse candidates, how you 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 is that it’s harder to naturally hold inclusive meetings. There’s a little bit of lag on Zoom, so it’s easier to cut each other off and it’s easy to kind of, without thinking about it, really exterminate the conversation.

One thing we tried at the start is this concept of silent meetings. We didn’t come up with this. I know Square and Amazon do it. The meeting leader comes in with a document and for the first 10 or 15 minutes or so, everyone’s reading the document, writing comments in there. And then only after that do we 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 there’s dramatically higher throughput, just from an engineering point of view. There are just 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, in that we weren’t necessarily always surfacing the best ideas because we didn’t have the fundamental mechanism to run the meetings on this front. 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 to really start to codify structure and pay equity with levels. And this tends to be more codified the way that 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. One fundamental thing from there is it’s just a lot more to do. And then two, you do want some of that flexibility – that’s just the value of an early stage startup. So we try to introduce just enough here so that fairness is paramount. The more fair the system, basically, you create more powerful incentives. 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 more the team feels there’s equity across the board, where they’re not having to lobby for it. It’s more like, heads-down, you work hard and you get paid more, your career grows. I certainly had the benefit of that working with and for Kevin and Wade. It’s worth trying to codify that part of the culture to make sure that the team really feels like there’s equity in place so it can just be heads down and 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 culture is 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?

I think ultimately every team has to translate culture or objectives as appropriate for the overall teams and functions. I can go through 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 as a company that has extremely high velocity. We care that being good today is better than being perfect tomorrow. Let’s just make that a constant cadence of daily progress.

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 joining the team you’re expected to ship code by the end of your first day. Now, we never give someone the gnarliest biz logic bug to fix, or 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 the instrument that gives us some more visibility to the stack. Something more minor of 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 why good today is better than perfect tomorrow.

We’ve actually had to tweak some of our onboarding practices to move some of the talks we normally did on day one to later in week one, or 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. You probably couldn’t do that unless you were enabled to know what the sales pitch is and what the pricing is, et cetera, but we can manifest that difference across engineering.

Another example that comes to mind for me is that we think a lot about ownership. And for me, the way I’ve really tried to think about that with my teams has been, If the only reason we, as engineers, take any action and do the work we’re doing is because the PM put it on the roadmap – and we ultimately 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?

Because ideally, if you’re an excellent owner, if you are in so much mastery and understanding of your systems that you are 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 to the team. Literally every Monday morning, the first thing that all the teams do is they go through operational metrics check-ins to say, Top to bottom here’s the SOAs, 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 on 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 de-prioritization versus one that was just not even realized or recognized as well. Does that ownership model look differently for a sales or a marketing person? Probably, but it’s just one of the ways we’ve tried to manifest that person for engineering, at least for these two different core values.

I would say that from the Grand Rounds Health side, I think that we are very diverse – and I mean in both geographies, but 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 in that every case matters and everything has to be dealt with that is specific to that episode of care and helping a member move through it. When you get on the EPD side, you have to be very concerned about those [different] instances and 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: Engineering, product and design.

It’s a great question on company culture versus team culture. Similar to what Wade said, it really resonated with me.

We also have a lot of different functions at the company. There are real estate operations, and even within real estate operations, there is 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 functional leaders (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 an easy trap to fall into because it’s an easy rallying cry.

A lot of fintech companies see this, and we’ve had to really check ourselves against this question of whether it is growth versus risk. That often lies in different functions: Oh, risk is on the way. That’s why we’re not hitting our ideal target. Oh, we’re doing bad deals or taking on too much risk. And that’s kind of a natural tension that will arise and it’s really important for those leaders of those functions to make sure that we’re on the same team and make sure it’s always laddered up.

I do think that strong cultures are not only created through those means, they’re created through other means as well. [They’re created] around shared rituals, to take Kevin’s and Wade’s examples, that may be different for an engineering team versus a sales team.

Where Ribbon specifically tries to put this in practice is that we’ve actually tried some versions of different principles or different core values for the teams. What we’ve always gone back to is actually translating the company core values. So now we have three core values at the company level, and then we translate that to the team level.

As a specific example, one of the company core values is to set new standards. We’re really pushing the bar on innovation. At the company level, that might be improving a certain process so that we can close on a home even faster. But on the engineering team, that gets into the technical world of where we used Amazon tech track (these OCR and document-parsing tools). We used them before, while it was still in beta stage, and we 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 [and thus able to] wake up any kind of competitive set in the space.

In the same way companies are pretty good at doing this on the OKR basis, I do think you want teams to set theirs in turn. I do think a similar pattern can be done on the culture basis as well.

That just reminds me of one thing I did that was a fun exercise. It was probably over two years ago, when I first joined the company, and it has still been very durable to this date. I just spent an afternoon and tried to write a one-page essay on what I called Good engineer, Bad engineer. It was inspired by Ben Horowitz’s very famous blog post Good PM, Bad PM, and I just basically personalized all of our core values at the corporate level to impersonalize and interpret them, and what it meant on an engineering level as well. It was 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 kinds of practices, but more as an aspirational kind of statement on what we should all be trying to do a little more of every single day.

It’s been really fun for me to write down my thoughts that way. And I also have it as a conversation starter with other engineers. Just, What are your beliefs and practices as an engineering leader? As an engineering developer? And kind of swap stories, understand, Are we really aligned to what we’re trying to build? Even on a personal level, we’re trying to aspire to get better on our own press 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 or the core values that you all have to find, where the opposite of them has to be just as reasonable? Because we all try to shy away from core values that don’t mean anything; like the opposite of integrity. It’s probably not something a company wants to have. But how do you define core values with 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, in that we really value Y, but to make it a little bit sharper-edged, we are actually introducing X.

The first one is impact over progress. We love progress. We want everything we do 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, whether it’s moving your own career forward or helping the team succeed, I hope you will think about making the team succeed first, 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, those are three examples of where we’ve tried to create greater contrast. We’ve tried to create greater contrast between going through the motions versus here’s something that actually creates a company value.

Yeah. I mean, the one I can add on top of that, too, is when we go through and we talk about culture, what candidates are coming in and we’re interviewing for the company, we actually always talk through here’s the core values and all these 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 be ready and fully aware and accepting of the fact that these are the flaws and what we’re going to take along the way because we’re prioritizing A over B.

So for example, we talk about velocity. We say these are the benefits we’ll get from saying, “Good today, perfect tomorrow.” 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 that centralized command and control structure. If those things frustrate you and you don’t want to do that, this is the wrong place for you.

Or one of our other core values is this ambition for excellence. Are we all getting better by 1% every day along the way? There’s an expectation explicitly that we all have to have a growth mindset expecting that we’re improving every single day. And if you don’t want to be in a place where there’s growth that’s stretching you to the point that it’s going to be uncomfortable, this is not the right place for you.

What I tell candidates personally is, “I hope I’m the right leader for this company in engineering today. I’m not confident – and 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 to kind of re-earn this job every single day.”

Now, for some people that’s a very menacing, threatening statement to make. You’re on notice all the time. For others, that’s an inspiring statement because, well, aren’t we all trying to get better and wanting to say, “Yeah, if I’m not better a year from 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 I do try to be very explicit upfront about this is what those norms mean for us. And also acknowledging, Here’s a discomfort it might cause some people, or this might actually be a very bad place for you if you don’t actually stand behind these statements and that kind of controversy.

Great. Kevin, Wade, Wei, 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 Greymatter. Thank you.

Thanks for having us.

Yeah. Thanks so much. Really fun and just glad we all spent some time talking about this really important topic.

Thank you Saam.


Saam Motamedi

Saam partners with enterprise software entrepreneurs at the seed and early stages who are focused on new opportunities in intelligent applications, cybersecurity, AI, and data infrastructure.

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