NM Live: How We Run a Remote Company Without Losing Alignment

Drew Sanocki

All right. All right, Mike. What are we doing here, Mike?

Michael Epstein

Drew, we just got out of our all hands and crazy to see the number of people at the all hands these days. I mean, we're well over a hundred people right now. And you know, the growth that we've had over the last couple of years is crazy. And it's super fun to see all the new faces show up sort of every time we have one of these all hands, but it makes you think about how we got here and like all the different phases we've gone through in such a compressed amount of time.

Drew Sanocki

Yeah. I love the all hands because I, I mean, we're at the level now where I don't know everything that's going on in the company. And so it's a good chance for me once a month to kind of hear what everybody's working on, you know, see some faces realize I actually have a company of humans, you know? And so let's talk about like some of the routines we do. So we're probably, I don't know, last time, 120 people was what I heard something like that. We do a monthly all hands. So that's the first Friday of the month. And we review, the previous month's performance and accomplishments and challenges. And then we look forward to the next month and kind of what we're going to do the next month. And we do it in sort of this round robin format. I mean, the first thing we do is have the head of finance get up and talk about the numbers for the business. We talk about some big corporate OKRs. You and I might go deep on some of our core values and give examples there. But then we let the department heads kind of cycle through and talk about what they've got going on. And I think it gets everybody front and center, holds everybody a little bit accountable to the whole team. And it works really well. I mean, we started with one a week and we found that the feedback we were getting was like interfering with everybody's week too much and, um, a bit redundant week to week. So we went once a month and that seems to work pretty well.

Michael Epstein

Yeah, I think this goes back, you and I have done this at previous companies together. I think the finance aspect of it is something that we've actually heard from a lot of folks is not as common, but very much appreciated. We did this at last at auto anything where we had our CFO stand up and really run through the numbers. Here's what's going well. Here's what's not going well. And the team really, really appreciated that level of transparency. Everyone, you know, we, think we found a lot of these turnarounds, especially a lot of the staff were sort of surprised when you told them the state of the business, like, I thought we were doing so well. We're making a hundred million dollars in revenue. How can we be losing all the, how can the company not be doing well? We're losing 10 million bucks. That's crazy.

Drew Sanocki

Yeah and I mean, the turnarounds were interesting because you'd sort of level set with everybody. And then everybody got into how are we going to make money? They were all throwing out ideas of how we could save money or make more. in our case now, I think we've just sort of carried that tradition forward. A lot of it's just rooted in a few books that made impacts on us. One of them is Powerful by Patty McCord. You you treat your people like adults. And you know, share all the numbers with everybody right there's no secrets

Michael Epstein

Yeah. And then it's also really hard for at our scale and at the scale of a lot of the brands that we've run is to understand what all the teams are working on. I mean, you, we, we hear all the time, everyone sort of wants to know, and then we want to know what's going on throughout the org, but especially, and even more so as a remote culture. It's really hard to keep everyone in the loop with everything that's going on. So people really get excited when they get a real preview and overview of what all these different teams accomplished and what they're working on right now.

Michael Epstein

Yeah, so I think today we also we talk a little bit about the different phases of growth and how you have to think about structuring the org or or managing the org as you go from you know startup or really small to over a hundred folks and Also, we've got an off-site coming up a management off-site coming up next week and how we're thinking about structuring that so that it's as productive as possible for our leadership team.

Drew Sanocki

Yeah, those are kind of the two things we do, the two routines we found to be really valuable. One is the all hands virtually. And then the others are these meetups. In this case, it's the management team. But I'd say every team has met face to face at least once through a year, probably twice in a different city. So we do a lot of that too. But maybe we start by talking about the different leadership challenges  that have happened along the way at different levels, right? Like I'm thinking back to when we started or in both of our startups in the early days, like when you've got under 10 million as a, as a direct to consumer brand typically means like one to 10 people working there. And so the leadership challenges there are the founder does everything. Like you've got to, you hire, you fire, you got to make sure the customer service team comes in and answers the phone at 8 a.m. You know, there's no middle management. Yeah. No one to delegate to, right? No hierarchy decisions get made quickly. Personally, I found like the first leadership challenge kind of kicks in, I guess we'll call it like 30 people, maybe 30 million in revenue. Where, you know, most direct to consumer brands, like that's kind of when you're building out middle management. You know, you've got your head of customer success or your head of marketing and you're in this position where you can kind of delegate. So the challenge comes from come it moves from like you got to do everything yourself to how do I delegate? How do I hold people accountable?

Michael Epstein

Yeah, and keep everyone coordinated too. So it becomes even more important as you start building out these management functions to ensure that everybody's rowing in the same direction. Also something that we ran into constantly, especially in the turnarounds was head of IT was like, here's what I'm working on this quarter because I decided these were the priorities.

The head of customer success says, decided these are my priorities for the quarter. Every other head of marketing had their own set of priorities, but none of them had actually talked to each other. They weren't doing anything that was objectively lined up to overall corporate objectives.

Drew Sanocki

Yeah, that's when, you know, at that 50, 30 to 50 million level, I think that's where I found OKRs to be valuable, the traction stuff. Like that's when you need your level 10 meeting to get department heads all on the same page. Public OKRs that the whole company can sort of rally around. And then the next inflection point, I think happens at around 100 employees. And that's kind of, you know, we probably hit that last year sometime, but I found it a whole new chat to be a whole new challenge. Like we had our OKRs, we had our level 10 meetings, we had our all hands, but there were new things popping up. I think the company tends to become bureaucratic. Any company tends to become bureaucratic at that size. You need more processes to coordinate people, and that by nature adds a layer of complexity to the business. Often you see execution kind of slow down in various groups because they're too hung up on decision making and process.

Michael Epstein

Yeah, you have to actively fight against that  and root it out as much as possible. It's inevitable that you'll have some and you need coordination among teams, but keeping that from becoming a bloated bureaucracy is always a work in progress, always a challenge for companies. I think something else is that, you know, that transition between going from a really small owner doing everything to delegation, to scale, like a real leadership scale. I remember, I don't remember where I heard this a long time ago, but it always stuck with me was like, at first you want to think about who can I find to start delegating things to that can get it done 80 % as well as I can to at least be able to start taking it off my plate. Then as you start to scale to the next level, it's like, who can actually take on these functions and do a much better job than I ever could. That's,  that's the phase that I think we're at now as well. And, and that's just a big,  I've always thought it is a great way of thinking about those, again, those different phases of growth. First, just trying to get certain things off your plate, then building out just this crack leadership team that just crushes within their own area, their, their own domains.

Drew Sanocki

Yeah, think early on, did it. We penned every email, every landing page, and ran meta ads ourselves. Then you go fast forward to today, where we have the resources and we really need to hire people who are so specialized. You can't just hire a marketer. You need an email marketer. I need to like a retention marketer, an acquisition marketer, a growth marketer. And they're way better, and they know way more about what's going on and what's cutting edge than I do right now. And I don't want to know about that stuff. That's kind of where we are. And the other thing I think you and I say a lot is culture eats strategy for breakfast. The most important thing is the culture. And I think when you get to 100 people, as a founder, your direct control really has waned. You know, we can't by force of will like we joke about how we physically at times have had to carry the whole company up a mountain. You know, in the early days, you feel like you're doing that, you're just like you're the only one who gets the vision. And you're trying to get this company up the side of a mountain. But like a hundred people, you just can't do it anymore. Like it's just too big. Like there's only so many hours in the day and everybody's remote. And it's like, I can't bear to hug a hundred, a hundred people. So you have to fall back on culture. And it's like, that's, I know when we hit a hundred, when we fit, when we hit the Honda was kind of when I started thinking about onboarding core values. You know, what we got to illustrate our core values. How are we going to train people in our core values? Like customer centric taking care of the customer, you know, like things that we've picked up along the way. I mean, you and I, let's just talk about one of PostPilot’s customer centricity, doing what's right in ownership, right for the customer. And I think we picked that up from Danny Meyer, who runs Shake Shack in New York and he's just runs great restaurant after great restaurant. He's got this idea of like, everybody at the whole company is empowered to pick up the sugar packet on the table. You know, if a busboy walks by a table at Union Square Cafe and there's like a mess, the busboy picks it up. You know, and it's like, at a big company or a biggish, you know, hundred person company, there are a lot of sugar packets out on the table. There's a lot of little messes that don't fit squarely within one person's area of responsibility. And so we really stress and we really recruit for, and we build a culture around ownership where, you know, if you see something wrong, you've got to fix it. You got to see it through until it's fixed, right? Whether it's in your department or not. So I found that at a hundred people, really leaning back and focusing on the culture is pretty important.

Michael Epstein

Yeah, another line that I like is  culture is what happens when the boss isn't looking and you're

Drew Sanocki

Yeah, which is pretty much everything now for us, right?

Michael Epstein

Right, so to your point, that is the only way to continue to execute at scale. One is, the two big takeaways that we landed on is frameworks to keep things organized and ensure the priorities are clear to the entire org and cascade down through each department using OKRs to keep everyone aligned, to keep everyone rowing in the same direction, keep everyone focused on priorities that roll up to the overall corporate objectives and priorities, and then focusing on reinforcing that culture so that people know how to act and what the right thing to do is without you having to keep your eye on everything.

Drew Sanocki

Yeah. All right, so here we are, 120 people or something. We got a management team. So everybody's coming together in New York next week. And I always go into these excited. Come out of them excited. I have fun with them. You know, we're going to meet up, we're going to have a couple social events, some fun dinners at some good restaurants and spend the day in Summit's office in Midtown and get real with each other. So let's talk a little bit about how to run a good management team offsite.

Michael Epstein

Sure, and to your point, so much of the value when you have a remote culture is obviously just physically being there in person. It's just that alone, bonding and  just rebuilding, continuing to nurture a lot of the relationships between these department heads and management team that all have so many dependencies on each other. Everyone's reliant on some other department or multiple other departments to be successful in their own job. So continuing to foster those relationships to keep those moving smoothly and executing well is super important. But specifically I think the number one thing that doesn't work well for off-site and often leadership meetings in general is when you throw up an agenda live when everyone shows up and they haven't had time to deeply think about the topics that you want to discuss. And then everyone just reacts in real time with whatever tends to be top of mind at that moment, or just they throw out whatever the first thing that comes to mind. And you go on these big tangents and you end up becoming really inefficient with the time because you're just spitballing a whole bunch of stuff that you didn't have time to deeply think about in advance and really get to the core things that you want to discuss. So pre-work, number one, is non-negotiable. Setting up that agenda and giving some folks some things to think about and prepare for in advance is probably my number one thing. I know we're doing some of that ahead of time. Did some interesting stuff around that Drew.

Drew Sanocki

We've done a lot of pre-work for this one. First thing, we got the agenda in front of everybody a week ahead of time. We had everyone on the management team take a personality assessment to assess their work styles.

Michael Epstein

We've also grown the leadership team pretty significantly over the last six months. So you have a lot of new people, new personalities, people that haven't worked together, have no history of working together in the past. So I think the leadership assessment's been really great to help rapidly understand how to best communicate with each other and new personalities that, again, you don't have a history of working with.

Drew Sanocki

Right, so we took this from Bridgewater, the big hedge fund.  We all did one. We dropped them into a GPT. And now we can ask all sorts of questions about how each of us should coordinate with each other. You and I got some tips on how we can work together better. So I found the pre-work is non-negotiable.  Personality assessment, another thing we did was a survey. So survey the company, survey the management team.  And we really dug there. I mean, we asked them to be pretty honest on  what is going well, what isn't going well. Who do you have conflicts with? Where are things getting lost between departments? And we're going to take the results of those surveys, and that's like the first half of the first day, is like going over these surveys, identifying the top issues so that we can divide up in teams and sort of tackle these issues.

Michael Epstein

Yeah, think it's getting what do we want to see more of from people? What's working really well? And how do we lean into those strengths? What are some of the weak spots that we have where maybe coordination isn't as tight as it could be? And how do we improve that level of coordination and collaboration?

Drew Sanocki

Right. Okay, so that's pre-work.  Second thing, structure for decisions, not discussions. What does that mean?

Michael Epstein

Yeah, I think again, one of the things that tends to go poorly at various meetings or off sites is when you just talk about a bunch of things for a really long time. And then you get to the end and go, what did we actually decide here? What's the actionable, what's the actionable takeaway that we are taking from that discussion? Otherwise you just created a super expensive retreat or super expensive meeting because you just took your leadership team out of, you know, out of their daily workflow to just talk for a while.

Drew Sanocki

Yeah. I mean, Amazon's got their memos that you need to bring to every meeting and everybody's got to read the memo. I think we're going to do a little bit of that. But then I really like  the entrepreneurial operating systems  IDS portion of level 10, which stands for identify, discuss and solve. That solution is critical. Like a lot of time to discuss an issue, to  identify the issue, discuss it, and then you want to always conclude with that solution. Most of the time, I hate to spoil it, most of the time you don't have complete consensus on the management team and you have to get in the habit of  just disagreeing and moving forward regardless. We'll agree to disagree, but we're going to decide on this. And  I think we're going to do a lot of that next week.

Michael Epstein

Yeah. Amazon has the concept of disagree and commit. We are going to get all of our opinions on the table. When you have a big management team, maybe not everybody's going to agree on the solution, but the key is we're committed to a path forward. also have that agenda and we have a structure so that again, it just doesn't go off the rails where we end up going on a bunch of tangents for, you know, hours at a time, it's key to have that agenda, keep people on task,  answer specific questions or go through specific exercises that are designed to achieve certain outcomes and not just let it become sort of this free form discussion.

Drew Sanocki

Yeah. So that leads into our third tip, which is having the right agenda for the days. I know what ours is essentially. We're going to present the problems and the survey results first. Like, hey, here's the challenges that were that we see as leaders that were revealed in the survey. Then we are going to have a discussion and breakout sessions to discuss various issues, breakout sessions if they're only pertaining to one or two people there. And then we come together to talk about, to decide and who's going to own what out of that decision and discuss execution. So those are the three sections to our day.

Michael Epstein

Yeah, and having a facilitator that keeps people on task, on topic, and moving through the agenda properly is a key part of just the overall workflow of the day.

Drew Sanocki

Yeah. And I would say keep it under six hours. mean, we've we, um, these things can really like, they could tire you out. You know, we're going to have caffeine.We're going to have bagels, every way. Got to have everything is going to be in this room. Um, I think we're in the room for breakfast and lunch. So there's a bit of like escape room mentality. But then hopefully we wrap up early afternoon and can, you know, go out into New York and then have a nice dinner together. Go to dodgeball, I think the first night is what we're lining up.OK, that brings us to the fourth tip, and that's use a decision making framework.

Michael Epstein

Yeah. So maybe a racy, you want to use a racy where you've just, once you've decided on this path forward, making sure that there's clear accountability, who owns what, who needs to be involved in executing those decisions. Clear,  recap of what was decided. So specifically, what was the action? What is the next step? Who is responsible for it? And then a commitment from those folks. sounds, I don't know, it sounds cheesy, but we always see recommended, like have people sign off on it potentially. Like something that just really  formalizes that commitment to what was decided in that conversation.

Drew Sanocki

Yeah, we like to take out a knife and cut our arms and like bleed onto a piece of paper to show the commitment. But other companies might do it a different way.

Michael Epstein

Yeah, yep. That's right.

‍Drew Sanocki

That's how we do it at Postpilot. Great. So I mean, I'm excited about the offsite next week. It should provide some, you know, a boost to go through the second half of the year, which I'm really excited about.

Michael Epstein

I am too.  The stuff we've got going on right now, we've been releasing a lot of new things, both that customers can see and behind the scenes to improve both performance and our efficiency. And the stuff we've got in the works right now continues to be some of the most exciting things I've ever worked on in my career. So can't wait to see that come out over the next quarter and excited to get the team all rallied behind it.

Drew Sanocki

Awesome.

Michael Epstein

So I think that's it, Drew. We've gone through a lot of these phases of growth, and we know that the people listening are at different phases, whether they're smaller startups or whether they're established companies. Hopefully this gave you a bit of a mental model to think about how to structure the org and improve overall alignment no matter what stage you're in. You can always use more clarity, always use more alignment as your team continues to grow. I know a lot of folks that are at off sites right now. So hopefully this is helpful to folks who might be planning one in the future. If you have tips or ideas for how you've run successful off sites, us a note too. We'd love to hear it.

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