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Second in Command: The Chief Behind the Chief with Cameron Herold
Ep. 591 - Twentyeight Health COO Mara Castro - How To Avoid These Deadly Traps in Operations Success
00:46:03
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- [00:00]
Mara Castro
I think that is a great way for you to truly understand the organization well, understand the team, understand, right? Like where there are opportunities for learning and investment on the team and also learning and investment on the infrastructure or processes and then ultimately come out with a plan that then you align with the executive leadership team where everybody feels like, okay, yes, we're aligned on this. Let's go and make this happen.
- [00:30]
Cameron Herold
Welcome to the Second in Command podcast produced by the COO alliance and brought to you by its founder, Cameron Herold. In the second in command podcast, we talk to top COOs who share the insights, strategies and tactics that made them the chief behind the chief. And now here's your co host, former COO of a multi eight figure remote company and alumni member of the COO Alliance, Savannah Brewer.
- [01:04]
Savannah Brewer
Today on Second in Command I'm joined by Mara Castro. She was employee number one at Warby Parker before it even launched and spent 11 years scaling their customer experience organization from one person to over 800. She then stepped into a $50 million P&L at Evolve, the fastest growing vacation rental company in North America, leading a 400 person team through a pandemic and coming out the other side with three, three times the revenue growth. Today she's CEO at 28 Health, a women's telehealth platform on a mission to make reproductive healthcare accessible to every woman in the country. Conversation. We get into how she aligns team priorities across her organization, even in domains where she's not even the expert in the room. We talk about the communication systems she uses to stay in sync with both her CEO and her team. The CEO COO dynamic, how to build and keep trust with your CEO and something most operators don't talk about enough, which is how to really care for your team and get ahead of burnout before it quietly takes your people out. If you're a second in command or you want to be, this one is worth your full attention. Let's dive in. We are live with Mara. Welcome to the show.
- [02:18]
Mara Castro
Thank you so much for having me.
- [02:20]
Savannah Brewer
Yeah, I'm really looking forward to this. Just already in our a brief little chat. It's been really nice getting to know you a little bit. So go ahead and share with our audience a little bit about you. Who are you and how did you end up in the position you're in? Yes.
- [02:36]
Mara Castro
So my name is Marc Castro. I'm COO at 28 Health. Who I am. I guess I'll start with a little bit of what you were asking me before. So I was born in Brazil Grew up in seven countries across the world and ultimately ended up landing in the us Started my career in nonprofits, was lucky enough to become the first employee hired at Warby Parker which was the most amazing experience I've had. And I know you're wearing Warby Parkers. Thank you for the support. Was there for 11 years and that's where I would say I grew up in my right like experience, leading customer experience, operations, some customer facing product, but really like the high growth intensity of what it is to work at a startup and scale so significantly like we did over the 11 years that I was there. And so that was a really foundational experience for me in learning that I really love to build and scale from the perspective of humans and building an amazing team and helping mentoring them and manage them and like really create a high performing team that is really united envision in objectives and working together and also in the terms of building and scaling infrastructure and processes. And that's just what makes my heart sing is just sort of like that planning process and really seeing things come to life. So that's ultimately where I grew up. I then transitioned to Evolve, which is a hospitality company, focus on vacation rentals. Was there for three and a half years and helped that company scale as well. Leading customer experience, the guest and owner experience. And then took a little break, a little sabbatical, nine month sabbatical. Because working in high growth environments sometimes, you know, takes a little toll on you. Especially throughout the pandemic, which was also the most amazing time of my life to focus on my two little girls. And then came back full force to join 28 Health as CEO in January of last year. A little bit over a year in this role here where I oversee product engineering, clinical operations, customer operations and pharmacy operations as well. Should I share a little bit about 28 Health and what we do?
- [04:58]
Savannah Brewer
Yeah.
- [04:58]
Mara Castro
So 28 Health is a women's telehealth platform, really delivering complete care for our members so women can get care for reproductive and sexual health care. Any urgent women's care needs like UTIs or BV, yeast infections, skin care and weight care. And how we try to help simplify the process of healthcare is if you have one of the 124 plans that we provide coverage for its clinical side, you get care for just your copay and from the convenience of your couch, you join a video session with your provider and get the care that you need and then get that prescription if you have one delivered to your home. And if not you can pay 1999 and get a also care through one of your providers for any of these needs that you might have on an ongoing basis.
- [05:52]
Savannah Brewer
Amazing. How did you get connected? Because it's interesting, these three companies, they're all very different verticals. How did you. What was like, the transition from Warby Parker to the real estate company to then 28 health and. And yeah, what made you interested in taking on a COO position in something very new?
- [06:14]
Mara Castro
Yeah, honestly, the transition from Warby Parker to evolve was. It was the pandemic, and we were in New York City and we were like, it's time to move, so let's just see what's out there. And evolve, reached out. And it just happened to be stars aligned. And the company seemed amazing, the leadership team. So it was an opportunity to leave New York and try something new. As much as I loved Warby, it had been 11 years, so let's go and try something new and learn a new industry. So that. That really excited me. Of course, jumping into a completely new industry takes some time for you to then really understand it. Right. Be able to fully immerse yourself in it. But that was an amazing journey. And then my transition to 28 Health was actually. I had been an advisor to 28 Health since 2018. So I knew the CEO, I knew the company well. I had been helping them a bit here and there. And then when I started to look, I talked to Bruno, our ce, and he was, you know, looking for a COO position. I hadn't necessarily thought of it for myself, but we started talking and again, stars just aligned, and here I am.
- [07:22]
Savannah Brewer
What do you think it was about you and that relationship? And his name is Bruno, Is that right?
- [07:27]
Mara Castro
Bruno.
- [07:27]
Savannah Brewer
Bruno. What about you or about that relationship made him want to extend that opportunity to you?
- [07:33]
Mara Castro
I mean, I think we knew each other well right from being an advisor from the early days. Plus he knew about my extensive experience in helping building and scale Warby Parker. So having that connection, having that trust, having that exposure to each other over the years. Right. I think ultimately the relationship of CEO and COO is one that has to be built on a lot of trust. So I think that foundation likely really helped us, you know, get that ultimately trust foundation to want to go into it from both sides and has been amazing for the last year and a half.
- [08:10]
Savannah Brewer
I've never interviewed any COO that said they got the job. Actually one one with a nonprofit, but she had already known them, and she went through the application process when they started hiring, but otherwise. And even then she still knew them. No One that I've interviewed has applied for the job. Like that just happened. It's all interesting. Previous relationships.
- [08:36]
Mara Castro
It makes sense. I mean, because I do think that the CEO role, right. Like, it can be so different in every company. And ultimately it's about being a great compliment to the CEO. And so, yeah, I think it just comes from that networking, that trust, like you're saying, and knowing each other, knowing where you could complement each other, then that's what ultimately then comes to be. That's interesting. I didn't. That's a fun fact.
- [09:05]
Savannah Brewer
What advice would you give to someone that might be listening? That they want to move into a CEO position, or maybe they're in one, but they want to find something better. And There are some COOs that are a little more introverted. They don't consider themselves as maybe strong in their networking. What advice would you give to those people who are listening, who are wanting to level up in their career and recognizing it's not going to come through an application process? What should they be focused on in building those relationships?
- [09:32]
Mara Castro
I mean, I am a little bit of a nerd. I love the Dale Carnegie book, How to Win Friends and Influence People. I think that's the full title. I totally forget.
- [09:40]
Savannah Brewer
Yes.
- [09:40]
Mara Castro
Such a classic, right? And I think ultimately it's about being true to who you are. Right. And honestly, also an introvert. I'm not the type of person that will, you know, I feel like I have friends that could talk to a wall. I'm not that type of person. But I can find moments of connection and then really build on those moments of connection in a way that feels authentic to me and ultimately. Right. Like just making it a point to reach out every now and then. Making sure that, like, I have this one mentor that I feel like was transformative in my life, Mike Schwartz. He was fantastic. And I feel like every now and then I feel like I need to go back to him and just be like, I'm so grateful to everything that you did for me and just sort of like connect and just learn about what he's doing.
- [10:26]
Savannah Brewer
Right.
- [10:26]
Mara Castro
So like those moments that you can find in your day to day, being honestly diligent about it too, and planning it out and making sure that you are following up with a connection every so often. But in a way that's authentic to you, that's what really matters most.
- [10:41]
Savannah Brewer
Yeah, that's really great advice. Okay, let's talk a little bit about coming into 28 Health. What were those initial 90 days like? What did you focus on? What did you learn and what did you experience?
- [10:55]
Mara Castro
This was my first time coming into a CEO role and also coming into the healthcare industry, which, wow, whammy. Yes, really. And so really the first. And I did this at Evolve as well. But my thought process in the first 90 days is to actually be counter to who I am as a person. Because who I am as a person is what I call a GSD person. I don't know if I can say that on the podcast, but. But I like to get shit done. And so ultimately it's about like those first 30 days is really controlling yourself to not and to really just listen. And so interviewing everybody in the organization, right? Or as many people as you can, depending on the size. And really coming intentionally to, okay, what's working, what's not working? My favorite question, if you had a magic wand, what would you fix and really start understanding, right? Like where is there overlapping? Where are there like true opportunities? Understanding them, right, like from the CEO, what is the vision of the organization? What are the strategic objectives for the year? How does that all come together so that you can then put together a plan of, okay, this is what we should focus on for the next 30 days and 60 days, right? And really work on delivering some small quick wins in the key areas of the business with some sort of like longer term plan, sort of improvements that we would want to see. I think that is a great way for you to truly understand the organization well, understand the team, understand, right? Like where there are opportunities for learning and investment on the team and also learning and investment on the infrastructure or processes and then ultimately come out with a plan that then you align with the executive leadership team where everybody feels like, okay, yes, we're aligned on this, let's go and make this happen.
- [12:47]
Savannah Brewer
How did you make sure when you're rolling out those projects not to get stuck in the weeds? This has been an ongoing skill I've been trying to learn is how to remain so high level without getting sucked into the projects. Because I just, I know if I can get in there, I can control the outcome in the way that I want to. So how did you start to align the initiatives and give the team the right info to execute without you getting so in the weeds on everything? Yes.
- [13:16]
Mara Castro
I think I would approach this in two ways. One is that alignment upfront, right. I really love the sort of Dymaic lean six Sigma thought process of spending a lot of time upfront in setting the vision, the objectives, what are the metrics, right? Like the KPIs making sure that everybody is fully aligned because if they are, then it makes it really easy for people to then execute seamlessly against that. So right. Like initially when I in it was about, okay, let's make sure that our vision is really strong, that everybody really understands that. What are the three key objectives for the year? What are our KPIs across the organization? Right. Company wide. But then also what are the KPIs for each department and how they all come together towards the main KPIs. But sort of like a KPI tree of uls. Right. To make sure that they all build up to that and ultimately also making sure that everybody is clear on their key KPI. Everybody should have one key, one that they're focused on. They could have a few supporting ones. But what is their main focus? And with that everybody is then right. Like really aligned in how they come up to build towards the impact of what the organization is focused on. From there, the sort of now getting to your weeds part of the question. I do think that there are times where it's really valuable for you to jump into the weeds. I feel like in my role I'm kind of like constantly doing this, you know, of just sort of like, okay, I should jump heavy into the weeds here. I've now set everybody up for success. We feel good. I'm going to come back up and maybe jump into the weeds somewhere else. You know, especially in areas where you're not as familiar with. Right. Like me jumping into healthcare and clinical ops and knowing like the crazy regulations and sort of like just all of the details that go into you going in network with plans. So. Right. Like especially with Medicaid and applying to a group and then applying to and how many providers and their credentials and their licenses and collaborative agreements. Like all of the details of. I had no idea coming in that was an area that I really needed to dive into deep to fully understand so that then I could hire the right people for the role and hold them accountable in the right way for the role. Make sure that we were aligned with the expectations to then come back up again.
- [15:48]
Savannah Brewer
Yeah. One of the things that you mentioned that is kind of standing out to me is the throughput of casting the vision and all these different reasons. Cameron has a book called the Vivid Vision for mostly like written for the CEO to get really clear on the vision and then for the CEO to help kind of set that. But you're right, there's also getting kind of more nitty gritty in the CEO position. You're constantly setting Vision if not for this whole huge grand scheme of what we're doing as the mission of the company, setting the Vision project to project KPI to KPI and why that's so important for the whole team.
- [16:26]
Mara Castro
Absolutely.
- [16:27]
Savannah Brewer
What about now? So that was kind of the initial 90 days, which was great. Thanks for sharing all of that. Now, day to day, what are you focused on? Where's your energy going?
- [16:37]
Mara Castro
Yeah, where is my energy going? It's the ensuring that we are focused on this transition that we're going through which we just launched, Complete Care. So I can walk you through a few of the learnings there. Ultimately we started the organization focused on birth control and access to birth control specifically. Over the years we introduced a few different products. So herpes, skincare, weight care, Get Care now, which is sort of like the urgent care needs for women. And ultimately. Right. Like our idea was to add value to the customer to make sure that they were able to get all of the care that they needed in one place, easily, conveniently, with no judgment. And what we found actually was that we made the business so complex that it was hard to understand how to pay for each one of these services and how they all came together. And so ultimately we went on this journey recently where we made everything fall into one membership called Complete Care. So that's the transition that we're going through right now. And kind of like how we were talking about earlier, right. It's. We needed to really focus on what is a vision and why are we going through this transition of now. Uniting everything under Complete Care, how should it come together? How do we bring all of the teams together to make this happen seamlessly? How do we communicate this in the best way to our users and make sure that ultimately they feel the value that they're getting through this. And so that is the key moment that we're going through as an organization right now to make sure that ultimately our users are getting the most value from this Complete Care membership and doing it in a seamless way that feels really easy and very valuable to the user in the end.
- [18:29]
Savannah Brewer
I'm curious for the membership, is there not or what's the upside to someone doing the membership instead of just like coming on a one off basis?
- [18:37]
Mara Castro
So people could come in a one off basis if they're on the insurance side of things. So it's just takes quite a bit of work to actually become a network with all of insurance plans and we do have 124 insurance plans that we provide coverage with across the nation. But for the plans that we don't have coverage. We do have this rate like $19.99 a month for the subscription service. And the reason why we think that's incredibly valuable is you can get all of these services for just the price of Netflix right for a month. And your health is worth a lot. And so we made very accessible. Plus, ultimately you get access to the provider on an ongoing basis, whatever question you may have. So let's say you start on a new birth control and you're feeling a few like, symptoms that don't feel great. You can send a message to the provider immediately and you get a highly trained and skilled MD or NP that is able to answer your question immediately and help you troubleshoot that. The same for skincare, the same for weight care. Right. Ultimately, that's what the value that we want to deliver to our users is that they could reach out to a person who has gone through years and years of training to get here, that is specialized in women's healthcare, that really cares about you to ensure that they're answering your questions within 24 hours to make sure that you never have any, like lingering questions that you're not going to AI to get your answers, that you're going to a medic, medically trained professional to help you with any of your healthcare questions that you have.
- [20:20]
Savannah Brewer
It makes a lot of sense. I actually just had a, you know, have a love hate relationship with Claude at this point. I like originally, like really, really loved him. And now there's been some things that I'm seeing where recommendations can be inaccurate, especially for me. I've gone through a pretty insane health journey. I have dozens and dozens of tests over the years and I have like a whole project in Claude about my health and I went back and forth with it for maybe 10 to 15 hours on. So wow, like having it with Google AI versus ChatGPT. Like having it. What's the word? Like, basically compete against each other to have accurate infills. And I still ended up because I have. My hormones have been irregular for a very long time. I created this plan. So the first time that I didn't use a coach or a practitioner to give me a new protocol based on my recent labs, and I started to feel crazy, like more and more emotionally irregular. And I was like, okay, I have to go figure out like, there must be something that I'm taking that wasn't actually aligned. And my best friend happens to be a naturopathic doctor and a hormone expert as well. So she looked at my plan and she's like, I cannot believe you're like you're taking one supplement that is doing the complete opposite of what you want it to be doing, which, oh no, I was trying to raise estrogen and I was doing something that would actually like deplete it more. And I got off of it and a couple days later I felt great. So I think there's going to be a lot of recognition over the next few years of people like, oh, I'll just use AI for this. And then realizing actually like, there's so many factors to look into and someone that's actually specialized in that thing and can take all the context is going to be really important.
- [22:12]
Mara Castro
Absolutely, yes. I'm sorry you had to go through that, but yes, you should learn it.
- [22:24]
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- [23:16]
Savannah Brewer
Okay, that was great. I had a question that also came out. Oh yeah. So the expanding outside of just birth control, there's some advice out there around just going really narrow and deep on one thing. And then like you said, when you start expanding out, there's just more complexity that comes with that. What was the decision behind or the thought process behind the decision to start expanding?
- [23:42]
Mara Castro
Yeah, our focus is women's health. So that's where we go narrow and deep.
- [23:47]
Savannah Brewer
Right.
- [23:47]
Mara Castro
Like that's our vision is to become really the leading insurance first women's telehealth platform. And we want women to feel like they can come for care judgment free, convenient, you can get a same day appointment and have it be incredibly easy because our lives are, you know, know, complicated enough. This should be the easy button. And the idea about expanding more products was ultimately to be able to make women's right, like healthcare easier. So that, okay, we started with birth control. We wanted to increase access, make sure right like that women that were. Sometimes we get messages from women that are in. I don't know, rural state moment that would have to drive two hours to get to a clinic. They jumped on their phone, they spoke to a provider, they got the birth control that they needed. You know, so like that was the key focus early on in the company. Then it was about, okay, how can we continue to increase the convenience? So herpes, skin care, UTIs. When you have the UTI, well you want the care immediately.
- [24:55]
Cameron Herold
So.
- [24:55]
Mara Castro
Right. Like also being able to provide that to women. Right. Like to answer your question, it's about going narrow and deep in women's healthcare, but really providing the breadth of scope for women to get the full care that they need.
- [25:07]
Savannah Brewer
When that complexity does come up, how do you manage that? How do you make sure that you're focusing on the right things and you don't start creating like this happens a lot in software, you know, or like SaaS as an example. Early on, like they're going after one thing and then over time this client asked for this and this client asked for that and then they're like, whoa, we have all of these things that we've created, all these things that we have to manage and we lost sight of like, like you said, like the core mission. So how do you stay focused on, on that core mission without. Yeah, creating too much complexity inside the team and in the business?
- [25:44]
Mara Castro
I would approach this in a couple different ways. One is always keep right, like the eye on the vision of women's telehealth platform and what makes it easy and convenient for women to get the care that they need. So that's our North Star and make sure that that North Star is always guiding any initiative that we're considering. From there, we want to make sure that the infrastructure that we're building is reducing that complexity as much as possible. Right. So how can we. Yes, healthcare is incredibly complex. We're nationwide, every state has its own regulations. But if we can create the systems and the processes internally, that helps simplify that as much as possible so that for example, providers don't have to memorize what state needs to do what the system just surfaces to them. This one you need to do an audio call. This one you need to do a video call. This one can be async and you can just respond via message. So have the systems, the infrastructure, the processes really do most of the work to simplify the day to day operations of the business. And then the second way of how to approach this also is just, you know, when you're considering a new launch, a new product, always thinking through, approaching things iteratively because then that would help you. Right. Like, really understand, okay, let's break things down to the lowest business value that we can deliver. Let's see if the value is really there and if it is, we can continue to build on top of it. If it's not, then let's maybe focus on something else that is delivering that business value. There's always that exchange. Right. Of and the assessment of what is really driving the impact that we want to see. And if there is one area of the business or a specific product or service that maybe isn't necessarily, let's maintain that and monitor it and let's keep it as it is. Let's invest in the areas that are actually delivering more of that impact that we want to see.
- [27:51]
Savannah Brewer
And when you're going about that in these domains that, that you're not necessarily an expert in, like engineering, clinical, I think pharmacy too, Right. So how are you going about leading people in these domains where you're not an expert in them?
- [28:06]
Mara Castro
Yes. This is the moment, right, where when you jump into a role like this and you're like, ooh, okay, haven't done many of these positions before, so let's figure this out. And the approach is always right, like curiosity. How can you really, one be really explicit with the people with you as a COO leading the vision of the organization, the objectives really helping, right. Like make sure that the entire organization is rowing in the right direction together. Ultimately, it's about making sure that everybody understands how they're connected to that larger vision and then making sure that you within each. Right, like vertical, that you're going down deep and understanding, okay, what are the opportunities here? Tell me more about, you know, your function. What are the key KPIs that we need to be looking at? What are the opportunities? And like I said, figuring out when you should be diving deep versus not. And so a few of these areas were doing really well when I joined. And so I was like. And this one area wasn't, for example. And so like, okay, I'm going to monitor and sort of just make sure that we're at a high level aligned here. I'm going to dive deep here and then when I come back out, maybe it's time for me to dive there, you know, and just making sure that you're asking the right questions that you are ultimately aligned in the vision to ensure that everybody is always moving in the same direction.
- [29:33]
Savannah Brewer
When you're moving in the same direction and things really start to go well and that scale is starting to happen One of the things that you mentioned in the kind of prep before the episode is that you'll have people on your team who are really talented but they haven't seen scale before. Some of the challenges that then come with that. And what's your approach to supporting those people as you're scaling?
- [29:54]
Mara Castro
Yeah, I honestly love leadership and managing and mentoring and you know, helping people plan ahead. I feel like, you know, I'm also just one of those people that even for my vacations I have spreadsheets. You know, I'm just a planner at heart. I love it. And so when I'm as right like leading operations within the organization, you're always trying to think two, three steps ahead and what does the team need to prepare for and how do you help them prepare for that. And so really figuring out where are the areas in the business where people are seeing a little bit of that and help provide maybe just a little bit of mentorship and guidance to where they can do it themselves but serve like little push and they're good versus potentially other areas where you need to actually dive deeper in and say okay, let's build out this spreadsheet, let's build out this approach. This is how we think about it and really help right like go into the project with them and help them actually go accomplish that planning process to set them up for success. And now that they've done it once, now they're able to do it again. So it's you know, sort of the same concept of what we were talking about earlier of knowing when to dive deep and not. And it's the same thing with leadership is knowing where your leaders are within the organization, what skills they have, what they've seen before, what they're able to bring to the table and in using those two to three steps ahead, being able to guide them there in, in the right way.
- [31:35]
Savannah Brewer
I love the just the approach of guiding sort of like because I think for some people it could feel like oh, this person's coming in to micromanage me or they don't trust in me. But really it's just playing team and supporting and guiding what he said in that like mentors capacity. I wanted to talk a little bit about your relationship with the CEO. One of the things that you had written in the prep was that the relationship is a division of energy, not just. Yes. What do you mean by that?
- [32:04]
Mara Castro
Yeah, I think like ultimately right when you're in a founder led business and right like the CEO has such an amazing and strong vision for the organization, there's a lot of energy that comes with that of sort of excitement and let's go and make this happen and get this done. And the CEO sometimes needs to come in and be like, okay, yes, we are going to do that, but here's the best way for us to do that. Right. Because if you have the entire company Moving at like 5x speed at all times, then that could lead to burnout for the team. And ultimately Right. Like is not the best position for everybody to be in at all times. And so you really sort of like come in to complement and say, yes, we should absolutely move quickly in this area and let's maybe deprioritize these other areas so that we can have the team focused on this and help really. Right. Like that's what I meant about like dividing the energy so that we can bring in that excitement, that vision that really motivates the entire team and gets everybody excited about where we're going with the okay, like here's the reality of how we can actually go ahead and accomplish that.
- [33:17]
Savannah Brewer
When you guys are talking about how to accomplish these things that he's excited about, what are the structures or systems that you have in place to staying in sync as you guys are going through? Because I'm sure you're so focused on all the things that you're focused on and he's focused on things. He is. How do you make sure that you guys are staying in sync? Think.
- [33:39]
Mara Castro
Yeah. Having prioritized list of initiatives that we are focusing on as an organization, we split those up across our executive leadership team on who's really involved and really leading each one of those initiatives. And so that ensures that there's always one executive really helping lead and guide each one of the initiatives that we've prioritized within the organization. And the entire organization has this list of initiatives. Initiatives to ensure that they know. Right. Like what we're focusing and what is number 1, 2, 3, 4, who's involved within each one of those. What are the key metrics that we're right. Like managing for each one of those. And then we come together, we have a sort of process of our Tuesday morning executive leadership team meeting where we review those initiatives, we talk about the key ones, make sure that we feel good about the progress in each one of those. We look at the KPI sheet for all of the initiatives and we make sure that all of them metrics are moving in the right direction. If they're not, why not? Let's discuss. And then we have a system of check ins throughout the week with the initiative members, or one on one, me and CEO, to make sure that we are always in alignment on what we're prioritizing, what we're focusing on, where the gaps within sort of these initiatives or within the organization and ultimately right, like keeping that constant communication to make sure that we're fully aligned across the week.
- [35:13]
Savannah Brewer
When there are things that come up where there's a difference in opinion or there's conflict, do you guys have any specific ways of communicating that help you move through that? Because that's one thing that also comes up with coos is sometimes feeling like they're holding back from really saying what they want to say and those go along with things and then that ends up creating an issue. So how do you make sure that you're bringing up the frank, honest conversations, but doing it in a way that still allows you guys to have a cohesive, safe relationship together?
- [35:44]
Mara Castro
I always make sure that I bring up if there's anything of concern that I think is bigger issue that we need to discuss, bring it up with the full data, the full picture, what this means to the business and then what are the recommended next steps from here, I feel like that always provides the full picture and also builds trust that we know what's going on and we have a plan around it and we have a plan on how to deal with it. And so usually those moments where they could potentially end up with a lot of friction is just sort of like, oh, okay, I fully understand. Maybe there's a few more questions. But yes, let's go and accomplish those next steps and align on what those are. I'm just gonna add, I always operate under right, like the principle of it's always best to raise the white flag and come early and often with those with just a, here's where this is. I just want you to be aware this is what we're doing about it versus if you were to keep that tight and then only come up when it's like a red flag and it's a bigger issue, then I feel like that really, truly erodes trust. Because then, like, you know, ultimately you need to make sure that that communication is always open and that you feel comfortable bringing those up. Because if not, then the CEO will just be waiting for, okay, when is the next red flag? You know, and I can't ever tr. Trust that everything is running smoothly or that I know what's going on within the business. That would be my recommendation, is always bring the white flag. Even if perhaps you don't have the full Picture, just saying, hey, you know, I have this situation, I'm looking into it, this is what I'm doing about it. I will bring the full picture later. But approaching it that way is, is the best way to build trust and maintain it.
- [37:29]
Savannah Brewer
Yes, Great advice. Reminds me, the CEO that I worked with had a company called Closers. He always told our executive team, no one ever gets in trouble from over communicating. I love that. So true. Like it might feel uncomfortable, it might feel unnecessary, but you're right. When you're just having those conversations up front, it eliminates the potential downstream of something actually bad happening. And then being like, whoa, I did not see this coming. Like, why weren't you looking at this? And you may have been, but you weren't in sync about it. And then it can erode trust over time.
- [38:04]
Genius Network Promoter
Yeah.
- [38:04]
Savannah Brewer
I love the white flag analogy. Going back to one of the things you had mentioned around burnout. I imagine in a company that's so mission driven, you probably have a lot of people who really care, maybe have their own personal, you know, ties to the mission. And also when you're scaling quickly, those two things can be a recipe for burnout. And there's also a lot of like different opinions on what burnout actually is and what to do about it. What is your, your kind of philosophy around it and how do you support your team in making sure that they're supported as you're scaling in that way.
- [38:37]
Mara Castro
It's an important conversation to have and to keep having within the organization. Yes, we do have amazing team of very mission driven teammates and we want to make sure that ultimately, right. Like the culture comes from the top and so that we're really leading by example and how we're operating within the business and how we're managing ourselves as well. And so ultimately what we try to do is as much as possible, like tomorrow, I'm not fully abiding by this, but on Fridays we try to have no meeting days and so try to maintain those as like heads down work days to make sure that people have at least one fully dedicated day where they're focused. And also.
- [39:26]
Savannah Brewer
Right.
- [39:27]
Mara Castro
Like it takes a lot out of you to be in video meetings all day because we are fully remote, so giving that rest from being on video the entire week. We also try to make sure that we're not slacking post hours. Right. Like we do have a team that's spread out across several time zones. So we try to maintain it within the sort of like eastern hour days, Eastern time zone. And.
- [39:51]
Cameron Herold
Right.
- [39:52]
Mara Castro
Like me, Bruno usually Try to never slack too early or too late within the day to make sure that ultimately people are able to log off and be able to have their life outside of work. Vacation as well. We're not the type of company that expects you to be with your computer on vacation and be logging on. I actually lead by example and also just try to completely turn off and not look at any slacks and just say if you need anything you can text me directly to my phone. A few of those different ways that we can make sure that we're helping the team understand that you don't have to be on 247 and then having ongoing conversations with the team. We always have monthly feedback sessions with all of my direct reports where we start the meeting asking, you know, where are you 1 to 10 with how you're feeling at the company right now? We talk about, you know, what could make it feel a little bit better. Usually it comes to being sort of like, well like I was talking to an engineer yesterday was he was mentioning sometimes I guess get quite interrupted during my day via Slack and I'm trying to, you know, focus on my priorities. And he just wanted to check is it okay for me to push back sometimes and you know, kind of like push people to self serve. And it's like absolutely, that's what you should be doing. So you know, being that mentor also for the teammates to help them manage their day to day in a better way to ensure that ultimately they have those moments of focus that they're feeling good about how their energy right is being managed throughout the day as well.
- [41:27]
Savannah Brewer
I love that personal touch and the understanding that like what may work for one person doesn't work for somebody else. And this is something I've really been coming to understand more about myself in the last couple years. Really beginning to learn about like highly sensitive people and that apparently I am one and even neurodivergency. And these things that I was so apprehensive to study because I didn't want the labels and I was like I'm just going to do my thing, like none of that matter. And as I've been learning more about it, I recognize for myself how I've actually really held myself back from creating spaces and environments and communicating in a way that would have set me up for way more success. And in doing that I realized, wow, there are probably so many people that have been on my team that if I would have really dropped in with them of hey, what is feeling good to you, what's not and really great it's not saying like, oh, you need to fit our standard or do it the way that we want to do it, but really working with people to fit their exact working needs. Yeah, it's been a big thing I've been learning, so I really appreciate that approach.
- [42:33]
Mara Castro
It's a big learning. Right. I mean, I also want to share. It wasn't always like this. I think in my last role, I did burn out. I was working into the wee hours of the night.
- [42:44]
Savannah Brewer
Right.
- [42:44]
Mara Castro
Like working at all hours of the time of the day and night. And ultimately I learned that, you know, it was taking a toll on my health and that's not how I wanted to live my life. And that's not how we should expect our teammates to live their lives either. Right. And ultimately, kind of a little bit like you had my health journey perimenopausal with my age and so, you know, things need to change a little bit. And so just started focusing on getting good sleep and really making sure that I was managing my energy throughout the day. And it really made me understand myself and understand that, like, we can still have such an amazing impact in the organization and do so much and actually we will do more if people aren't burned out.
- [43:31]
Savannah Brewer
Totally agree. Thanks for sharing that personal vulnerability as well. Yeah, this has been amazing, Mara. Thank you. I always love to wrap up by asking, what are you most excited about in the next six months, both in business and personally?
- [43:47]
Mara Castro
Love this question. I would say the main thing, business wise, would be to really continue to deliver more value to our users. You know, always continuously thinking about, I think I grew up being in customer experience. Right. And I think Warby, honestly, Warby Parker is a, I think the beacon of putting your customers first, really understanding your customers and making sure that they're always getting the best value. Really feeling loved by the business and so bringing that to 28 health. Right. Really thinking about healthcare is so complicated and how can we really try to make that less complicated for women, make it really easy for them and get them the full care that they need. So continuing to think of new products, new services that we can add to the complete care membership so that members really feel like ultimately healthcare is easy and I can come to 28 and get the healthcare that I need. So that on the business perspective and then on the personal side, being originally from Brazil, being born there, the World cup is officially here. Very excited about seeing the games over the next few weeks and enjoying summer, enjoying summer with my family and so just, you know, enjoying a little bit of that crazy World cup time that comes every four years with the family now, because now that my girls are nine and seven, it's, you know, it's a little bit of a different ballgame with them as well. Well.
- [45:18]
Savannah Brewer
Oh, I love that. Well, I hope that is everything that you would imagine it to be. And thank you. Thank you so much for coming on and sharing your wisdom and your experience. Really appreciate your time.
- [45:31]
Mara Castro
Thank you so much for having me. It was lovely.
- [45:33]
Savannah Brewer
Take care.
- [45:35]
Cameron Herold
You've been listening to Second In Command, brought to you by COO alliance founder Cameron Herold. If you enjoyed this episode, please be sure to like, share and subscribe to us on Apple Podcasts, Spotify and our other podcast streaming platforms. For more best practices from industry leading COOs, visit COOAlliance.com.