10 Key Lessons from Steadily's Unique Culture

Hey there, I'm Daa Santo Mier, co-founder of Steadily. Today I'm excited to talk with you about Steadily's unique culture. It's not lip service for us — we live and breathe this culture. It influences every decision that we make and how we lead the company. That culture is what's helped us not just attract but also retain some of the brightest talents in the industry.

Some people think that great culture is all about flashy perks like no-meeting Fridays, nap rooms, sushi lunches every day. And while we think those perks are fun — don't get me wrong, I love no-meeting Wednesdays, I live by it — we see our culture differently. Our culture can be polarizing. You either love it or hate it; there's usually no in between. The people who love it tell us that they love how we say what everybody else is thinking but nobody has the guts to say out loud. Something we've heard from lots of our team members is that they've come from places where they were frustrated because they were the only ones who really cared about their job. They could outwork their peers but were still making the same amount of money. Other people read it and decide our culture isn't for them — that's okay. We respect that our culture isn't for everyone.

It's about building a team of people who've caught the vision of what we're trying to build and are excited about it. They understand how the work that they do fits into the grander scheme of things, and they aren't just a cog in a wheel — they're a critical part of the success of the amazing thing that we're building. I'd like to share 10 key lessons we've picked up along the way.

We've all worked on teams where there were one or two people who just really shined. They could outwork the average person on their team by double, they consistently produced excellent work, and they carried the weight for the whole team. We had this theory when we were starting Steadily, which has really turned into our core philosophy: what if we could build a team made up of nothing but those types of people — people who were the very best at what they do, the top 10% in their respective roles? How much more could we accomplish, and how much faster, if everyone on the team was firing on all cylinders? The last three and a half years has proven how much we can accomplish.

That's what we're trying to gauge during the interview process. It's not whether or not the person can do the job, but is this a person who holds themselves to a personal level of excellence that goes above and beyond their peers in their current role? If yes, we want you on the team. You're going to be a great fit here at Steadily.

Lesson number two is: big salary is efficient. Let's be real — if you're trying to hire and retain the people who are the best at what they do, you can't expect to pay them pennies. One outstanding employee gets more done and costs less than two adequate employees, so we need to compensate them accordingly. Lesson number two is to make sure our compensation is near the top for a role or an individual's market value.

We noticed that a lot of tech companies offer perks like free gym membership, pet insurance, that sort of thing. But the reality is that people value those things differently based on where they're at in life. So what we did is take all the money that we would have spent on those little perks and instead funnel it into offering the most competitive salary and equity that we could. Now, don't get me wrong — we still offer traditional health insurance plans and access to all of the other coverages and things that people need to protect their families. But I think sometimes people on the surface think that because we're not paying 100% of healthcare coverage it's because we're cheap. We're not. We could — absolutely we could — but knowing that people value those things differently, we want to give people the freedom to choose where their money goes. So we'd rather pack it all into the highest salary that we can instead of offering very rich benefits.

Lesson number three: everyone has equity in the company. That's something that makes Steadily unique and something we've insisted on since the beginning. We don't just offer equity to senior leaders — every single person who joins Steadily is offered equity in the company, because we want them to have a personal investment in what they're building. They're not building it for us; they're building it for themselves, so that they can enjoy the reward someday of all of their hard work.

Something that throws people off sometimes is when we say at Steadily we're not a family — we're a team. They're so accustomed to hearing companies talk about being a family. We aren't. We draw this analogy to the pro sports team: we're drafting the top picks in every role to come and join the All-Star team at Steadily. We run lean, and every person on this team has a critical role to play. If they're not playing that role or they don't bring their A-game, that team doesn't win that day. The reality is we just can't afford to have folks on the team who aren't pulling their weight.

I think that's part of what attracts people to Steadily. It's nice to be part of a winning team, but they also love the impact that they have — how they can see the results of their own work driving up the team's sales for the day or pushing the team's retention percentage over goal. There's really nothing like seeing the impact of your own work and what it does to the company.

Part of the benefit of hiring rock stars in every role is that you can trust them to do the right thing day in and day out. One of the things you'll find here at Steadily is that we have very little hierarchy. We've intentionally created a very flat org structure. This means that we don't have any managers who only have one or two direct reports. Instead, what you'll find is that leaders have a broad range of direct reports who might range from individual contributors to leaders.

Our leaders are also workers — that's a key element of our culture here at Steadily. We don't have any ivory tower leaders who sit in their offices and have no idea how the business actually gets done. Every single one of our leaders can deep-dive into the weeds when they need to and can do the day-to-day work of their team when they need to. That's how they built these incredible teams — they have learned and perfected the workflows and processes themselves. This lets us stay more agile and make decisions faster, because you don't have 10 layers between the most senior leaders and the most entry-level folks. Today there are only two layers between me and any given team member at Steadily. That means ideas and information can reach me so much faster than if I were four or five levels removed from the things that happen every day.

I was that kid growing up who, if you gave me a direct order to do something, I'm probably going to do the opposite just to see what would happen. I'm still a little bit that way. But if you give me the context and the why behind what I'm being asked to do, I'll do it all day long. Have you ever been on the phone with somebody in a call center and you could tell they were just reading a canned script, even though it was totally inappropriate for the situation? It just made you more angry. We never want to create a team who just blindly follows scripts and procedures even when it doesn't make any sense.

We believe that by leading through context, stellar team members can operate within that context to make judgment calls that are good for the customer and for the company. Now, that's not to say we don't have policies and procedures — we're in the insurance industry, so we absolutely do. But here's an example of where a team member exercised that context in a way that made sense. We had an account manager on our client experience team who knew that our process said to process a payment through a secondary platform instead of the primary platform. But for this particular customer, his policy was about to cancel, and he knew that if he used the secondary platform it would be several days before the payment would process back, and that policy would long since be cancelled — which would create more trouble for the company and for the customer. So he made a judgment call that for that occasion he was going to process the payment through the primary platform, even though that wasn't what the procedure told him to do. We celebrated that. That was the right thing for him to do, because he used the context that he had to make a judgment call that was in the best interest of the company and the customer. That's the kind of person we want at Steadily.

That level of responsibility requires having exceptional people in every role. They aren't just filling a position — they know why they're doing what they're doing, and they show good judgment when they exercise that freedom. There are certain ways that cases have to be handled, and there are specific things we have to state. What freedom looks like in these types of roles is that we're not going to micromanage our team — we're not going to check in with someone every day to make sure they started work on time, we're not going to ping them when they've been gone for five minutes to ask where they are. We do, however, pull data on everything. We know what somebody's doing all day. We know if they're starting their day after their scheduled time, we know if they're skipping out early every Friday. We don't have time to micromanage people, so if we have to micromanage someone, we've hired the wrong person. If at the end of the week or the month we look at the data and we see that someone is abusing that freedom and they're not taking responsibility to do the things they know they were hired to do, then we might conclude that they aren't the right fit for Steadily.

In creative roles like marketing and engineering, there's a lot of freedom to do what you need to do. We try to remove the red tape. Good process means an engineer is going to have a peer review their code before they deploy it into production, but we're not so rigid that you're only allowed to post code on a set schedule. Marketing doesn't have to get approval for every copy that they deploy. They operate within the freedom of their role and are responsible for the output staying within the context that they've been provided and showing excellent judgment. That's the whole point of hiring folks in the 90th percentile — a leader can set the context and they run with it. They don't need their hand held. They don't need you to check in with them every day. If they don't know the answer, they're going to figure it out.

I've heard managers who join Steadily comment several times how refreshing it is — how different it is to have an idea and just be able to run with it, versus their experience at prior companies where even the tiniest change would take weeks to run up the flagpole and months to get implemented. That's the beauty of having an agile organization like Steadily.

Transparency is the foundation of trust at Steadily. During the interview process you'll find us nothing if not direct. Our job is to make sure the candidate understands exactly what they're walking into. There's no smoke and mirrors here. Our goal isn't to trick someone into coming to work for us and then find the job totally different from what they expected. That's why we put it all out there on the table from the beginning. If we tell you a thing is going to be hard, it's going to be hard. If we tell you you're going to have to put in extra time to be successful, it's the truth.

In our culture deck we have a slide: "Be honest always." As a Steadily leader, no one in your group should be materially surprised by your views. This means as leaders it's incumbent upon us to be direct and honest about how someone is performing. It also means that we welcome constructive discussion and disagreement. We have another slide called "Disagree and commit." We may disagree vehemently behind closed doors — we're going to respectfully talk through it, we may have strongly opposing viewpoints — and then we're going to come to a decision that may be one the other party does not like. But once they've had their say, they're going to commit to the decision. Once we leave that room and the discussion has been closed, we're going to sell that decision as if we were its biggest advocate. Our team is never going to know that we strongly dissented behind closed doors. We're not going to sabotage the decision or half-heartedly implement it because we didn't really like it. We're all in at Steadily.

We have a culture deck. We drew initially from the Netflix book No Rules Rules and from Amazon culture, but over time we've tailored these ideas to fit our unique mission at Steadily. Periodically we pause and ask ourselves: is what we're doing in alignment with the culture deck? If it's not, then we talk about it and we either change what we're doing to reflect the culture, or we update the culture deck. It's not intended to be aspirational — it's intended to be a reflection of how things really are. We're on our seventh iteration now, so you can see how we continue to evolve as an organization while staying true to the core elements of our culture. Our culture playbook reflects our ongoing commitment to maintaining excellence. Just because something worked for us three years ago doesn't mean it will still work for us today. This constant refinement helps us stay agile and responsive as a company.

You have to work to preserve culture. I often get asked: how do we preserve culture as the organization grows? You have to keep it at the forefront of your mind. You have to talk about it all the time. You have to insist on it and make sacrifices to ensure you're upholding your standards. You have to make hard cuts sometimes. Sometimes when I'm interviewing, a candidate will ask me, "When are you going to close this role? When are you going to make a decision on this position?" The answer is: when we find the right person. If we don't find the right person, we're going to keep that position open until we find them. We will not just put someone in a seat because we're desperate to fill a role.

I talk about culture at least twice a day. We send out the culture deck to every candidate and we talk about it at every stage of the interview process. I'm pretty sure the people who sit outside of my office are so tired of hearing me say the same things over and over again — but that's how we preserve it. As we've hired the next generation of leaders at Steadily, they've heard us talk about it a hundred times, and now it's their turn to turn around and share the same messaging. I'm delighted when candidates tell me, "Oh yeah, I heard that several times already — everyone I talked to said the same thing." Great. That's what success sounds like.

So you're thinking about joining Steadily — maybe you're a little nervous about joining a company that hasn't been around for 20 years. I get it. But the opportunity to be part of something where you have a real impact is like nothing else. And the reality is, if you look at the traditional companies, they've been doing layoffs left and right. So if you want to talk about risk — something that's a benefit for Steadily is how lean we run. Because we run lean, we don't have any fluff roles. There's nothing to get rid of. We need everyone who is here and we need everyone firing on all cylinders.

Thanks for stopping by to explore Steadily's culture. If our culture resonates with you and you would love to be part of Steadily's winning team, we'd love to chat with you about one of our open positions. Please submit your application on our careers page and we'll be in touch.