Stephen Hedlund on Running Marketing Like Finance (and Making It Work)

Overview:

In this episode, Elijah Drown sits down with Stephen Hedlund, a marketer with a finance brain and a startup heart. Stephen unpacks how treating marketing like a performance-driven business unit—not a cost center—transformed his team’s approach to brand, content, and pipeline. From leveraging memes and in-person events to using real-time feedback loops and founder voices, Stephen shares scrappy, scalable tactics that build trust and drive revenue. Whether you're a founder, a first marketer, or just trying to make your marketing budget work harder, this episode offers tactical clarity and a whole lot of candor.

Transcript:

Stephen: It exploded. Like most of my, you know, content was seen by, you know, I don't know, 10, 20, maybe 100 people most of the time. This one got 150,000 questions in like two days.

Elijah: He's behind every big funding round, someone doing five jobs at once. Really, that someone is Stephen Headland. Spoiler: he's the guest today. As head of finance, Stephen helped lead the 25 million series A round recently backed by Sequoia, but that's just the start. He's deep in the trenches posting social content and running live demos, which I attended.

That was cool. And doing some merch, I've learned on his own somehow and figuring out how SAS marketing works on the fly. He'll tell you later that as a finance guy, he hates that marketing works. But for now, experience at Walmart and Mercury, Stephen brings a rare combo: financial rigor, startup scrappiness. And he joins us to talk about not as a marketing leader, but what it takes to grow a company when the playbook doesn't even exist yet. I'm Elijah, marketing director at MKG. You're listening to Tea Time with Tech Marketing podcast. Stephen, like serious, is this how you kind of run the show at Rillet every day? Like super polished, super perfect?

Stephen: I don't know how to say super polished, but super detailed. Yeah. I think you have to be.

Elijah: Well, yeah, when you're used to finance, you're used to doing the debits and the credits and figuring out where the black line is and the red line is because I'm high level. I'm sorry. There is a lot of detail numbers. Everything matters. So it makes sense. Yeah.

Stephen: We have to be very thorough.

Elijah: It in. I'm not always thorough, but I like to entertain as you know, as a creative, you're kind enough to tolerate my zaniness. So if I could, could we try a little segment, get us warmed up, have a little fun? Let's do it. Cool.

So I like to coin this as weight. Is this marketing? I just thought of this title, but I'm going to throw a whole bunch of stuff at you about 10 phrases. You got to figure out if it's that's marketing.

Maybe it's a cry for help or somewhere in between. Any questions? Let's do it. Awesome. So at first off, we'll say replaced, close the books faster with slay the spreadsheet beast in a demo deck just to see if anyone noticed.

Stephen: Yeah, definitely not marketing. A little bit of crazy.

Elijah: It's not a cry for help. Just somewhere weird and wild. Yeah, I love it. And you love memes and you like to post memes about accounting stress at 11 PM, but you only get two likes.

Stephen: Oh yeah, that happens all the time. You got to got to treat a content like a rap machine or a rap album.

Elijah: Do you rock in a corner when you cry to like, ah, I can't. I'm getting absolutely. Yeah, I hope myself that scrappiness. I love it. You updated a homepage headline six times in one week.

Stephen: Whatever it takes. Definitely marketing.

Elijah: Live demo in the kitchen while the dishwasher was running. That has to sound like Steven. Yeah, that probably happened. Okay. Did you ever use a support ticket? It uses as a response to a LinkedIn post?

Stephen: Oh, all the time. Yeah. You've got to get content from everywhere.

Elijah: That's what supports for feed. I like that. Maybe you forgot to record a webinar of a live demo and you sent it out as a blog post instead. Does that sound familiar?

Stephen: I have forgotten to record a lot of webinars.

Elijah: Love this. Oh, the one I love is I told investor we're building a content engine, but meant to say, but really meant I'm editing a blog post in Google at midnight. What's the difference? Oh, you're always up at midnight like quarter to 12. You're like, I'm editing a document. This is fun. Like you never sleep.

It's crazy. And did you ever add my ERP is sexy to a pitch dock as a placeholder? Never move it. Only once. Yeah. That's why Nicholas goes, I don't know about this guy, but you're still hired.

Stephen: That's not the client did not notice. So it all worked out.

Elijah: I love that. And you announced the series A and a blog post and on LinkedIn, but you forgot to text Koya, hopefully not the case for you.

Stephen: I think we tagged them, but I should go check.

Elijah: Just now. I know. Oh yeah. In entered second thoughts. I'm like, Oh God, did I screw this up? I can't. It's a big play. This whole thing about Rillet is, is fancy. You guys are into finance. You're kind of revolutionizing the way things done are done. Unlike some comp competitors who we may or may not mention later. The Rillet's mission is to make the zero day closer reality. So what does that mean? And what's the biggest misconception have when they hear that? If I may.

Stephen: Yeah, it's a good question. So for those who aren't deep in the weeds on, on finance and accounting, closing the books just means bringing all the financial numbers together at the end of the month. So you know, kind of the health of the business.

Elijah: So how long does that close usually take without the magic or really like forever?

Stephen: So I've, I've worked at the company where it took us a month and a half. Most companies are usually around 10 to 15 days. We had a customer come recently to real that they were on eight days before now and really, there are four days pushing to three.

Elijah: So Rillet's mission is to make a zero-day close a reality. What does that mean? And what is the biggest misconception people have when they hear that?

Stephen: Yeah, for those not familiar, closing the books just means bringing in all the financials together. So you get a view of the health of the company. So knowing all the dollars that came in, all the dollars that went out and kind of where you stand at the end of the month. Cool.

Elijah: I couldn't have said any better. The technology behind Rillet, if I could dive into, we didn't really prep for this, but I know you're locked in on the demos. Can you kind of help give a high level of how things operate behind the scenes and how the magic or Rillet happens? Did I put you on the spot? Too much prayer.

Stephen: I'm trying to think about this. I'm not like I'm not the tech guy.

Elijah: Do we call support?

Stephen: They can help. Yeah, probably they could help us.

Elijah: Yeah, those things and stuff and makes it faster. Is there anything without the tech that you're getting into? Is there a differentiator maybe between the competition that you guys are proud of?

Stephen: When we talk about biggest misconception of kind of zero day close, the key thing to call out there is that that is our vision. We're not there yet. So we have folks asking like, Hey, does that happen today?

The short answer is no. The way we kind of get there as a company, as a profession is to both use AI and then just good old software automation and having really good software to kind of accelerate what accountants are doing every single day so that we can get there. So we're not there yet, but that's the vision of really.

Elijah: So it's more like saving time and getting workflow efficiencies going and having this like dashboard or this ultimate one stop shop thing that you load up. Maybe it's a web browser-based. It's an app, whatever it may be.

And you just kind of lock it in, put in some numbers, a whole lot of spreadsheets and then just fire it off and 20 minutes later it's done. Not quite like that, but am I getting closer? Yeah, exactly. That's that's the vision.

That's what we're working towards. I really paid attention to that demo. You sure did. That's nice. Hey, we're getting along.

This is good. And we're figuring things out on the fly. So here we're learning and that's kind of the whole thing that you're learning.

But I know you don't like to be sold on stuff, but you really love the product to really. So is there a bigger evangelist? Is it you or the CEO necklace? That's a good question.

Stephen: So I have this thesis that I think is is coming into fruition now in that I think every company should have what I call it evangelist. Yeah. Internally and it's it's someone who could be a customer of your product, but instead they work at your company and they're just really loud about it. And so in our case, like myself in my prior roles, I've worked in finance and accounting and now I work at a finance and accounting software company and I just get to talk about what really does and I can do that both at, you know, on LinkedIn, for example, doing lots of posting can also go and host dinners for real it and connect with peers who are doing, you know, finance at their companies rather than just be saying in sales. Right. I, I think this is the, the future of BDM marketing. I think everyone will have a role like this in the future.

Elijah: I'm curious if you dialed into the perfect dinner to maximize the, the spend on the stake to the ROI. Are you there yet? Have you crunched the numbers?

Stephen: That's a great question. So as a prior finance guy that now runs marketing, I would love to have really clean and clear analytics on all of our marketing spend. The short answer is that it's mostly vibe marketing.

I had a friend ask me recently how we're measuring our ally on our different marketing channels and the short answer is I have no idea. I don't have time to sit down and do the analysis and, and figure out exactly how we need to optimize here. We're just going with what works.

Right. So we hosted dinner. We cold invite a bunch of CFOs and one of those CFOs becomes a customer two months later. Oh, great. Let's do a lot more dinners. Right. That's what we do. If we sponsor a newsletter and sponsor a couple of newsletters and don't really get a lot of traction there.

Well, let's not do more newsletters. Right. So we are very much kind of going where we see traction and continuing to double down there. And as we go over, we'll find the dollars, but right now we've, we've stayed very scrappy. So any way we acquire a customer today is net positive for us.

Elijah: Yeah, absolutely. If you're not going backwards, it's a great thing. Yeah, exactly. I like that. I like that a lot. The, if I may give you a quick tip on the fly, a direct, indirect attribution is going to be the phrase that's going to excuse any data points that you can't find. So if you use that, you'll sound fancy and you'll kind of get away with not really knowing what's going on because that's kind of the vibe marketing feel. So if you want to try it, we'll see how it works. And all the marketing is going to go, Oh God, they're slamming their head on the desk, they're rolling their eyes. They're like, I know what you mean. So hopefully it'll help.

Stephen: Oh, thanks. The, the frustrated thing with marketing is it's so hard to know what actually works. Yeah. Right. Is you can, you can draw some clear lines, but it's often you need multiple touch points for people. Well, I can bite them to a dinner. I'll connect with them on LinkedIn. They'll see my content. We'll exchange DMs over LinkedIn casually.

We'll connect over coffee as friends again in three months. And then three months later, they buy really it. It's, it's very much not a kind of, you know, I guess like D to C business. Right. When you see an Instagram ad and then you suddenly buy the product, it's, it's a very different kind of motion here.

Elijah: Do you think it's the marketing play that makes you really feel out of your depth? Is there a way you got through it? Or is that maybe before Rillet that you're like at Walmart? I go, I don't even know where to start with an international company.

Stephen: I mean, I, I still feel pretty clueless on the marketing front, if I'm honest. Yeah. I've, I've been running it now at Rillet for the last, I guess six months. And it kind of happened by, by accident. So I, I came in to run kind of go to market and partnerships. And then three months into roll, I built a, I made a meme.

About a, about Rillet and about Netsuite. And I sent it to my CEO. Is that, haha, isn't this funny? Um, and he turned around and posted it on LinkedIn. And it went really well. Um, people loved it. Lots of engagement.

And he came back to me the next day and said, Hey, do more of these. And so that was, that was kind of the first start into marketing. And then about two months after that, um, I wrote a post for my personal account about why I thought our kind of lead competitor, um, kind of legacy competitor basically would not exist.

And in 10 years. And it was a bit, a bit spicy, you know, probably, probably a little more, um, spicy than maybe I should have made it, but the, it exploded. Like most, most of my, you know, content was seen by, you know, I don't know, 10, 20, maybe a hundred people most of the time. This one got 150,000 impressions in like two days.

Elijah: And I think I actually saw people tagging, uh, the competitor be like, Oh, by the way, just so you know, somebody's going to take over. So wake up. It was awesome.

Stephen: They did. It was, it was amazing. There were even other competitors that were then jumping on to the comment thread and saying, Hey, if you don't like this one, you know, come check on us. And I loved it.

Elijah: Um, so I'm curious if some other competitor comes on your comments and goes, Hey, you should try us and you're like, hello, I'm really, you should, you know, that you're competing and you're taking away your steam.

Stephen: Like, I'll be honest. I love it. Yeah. The engagement is king, right? So when they comment on my post, it's going to feed into all of their connections, LinkedIn feeds, right? So please comment on the post, please boost it. You know, share, share really with all of your potential customers and current customers.

Elijah: I mean, you can't succeed alone on sexy new headshots. Like you need some help from the community and that seems to be the vibe. You guys are hanging, uh, supporting everybody and just being cool.

And maybe that's how you close the $25 million series A with Sequoia last year was 13 and a half roughly this year at Sequoia. So you got some traction. Has it actually changed? Like, is the merch better? Do you got cooler hats?

Is there, you know, more Disney trips? I can't tell you about that because, you know, the Sequoia is listening, but you get the idea. It's a lot changed or you guys still humble and cool.

Stephen: I hope we always stay kind of humble internally. It's, it's funny working in a company of mostly accountants and finance folks. Is it's, it's a very different vibe from prior companies I've worked in. There, there's kind of a stereotype of accountants and all of there is a being very introverted, not flashy. I'm not kind of wanting to be in the spotlight.

That's kind of all of, all of really internally is, is really folks who are razor sharp, intelligent, but don't want to be in the spotlight. So it's, it's even very odd for myself and our founder to be posting on LinkedIn aggressively and to kind of be out there publicly. But it makes a massive difference for our business. So starting in, I started posting consistently on LinkedIn in January of this year. We got our founder posting consistently, kind of his stories in March, and it has entirely transformed how people interact with the company and with the brand.

Elijah: It's kind of weird how humans, even on behind the screen, want a human or whatever it's called, right? It just, who knows? And you're talking about your kids. So obviously you're posting more attentional, try to lean into who you are.

And you want to have that connection because you can't meet everybody. Is that the shift that you're talking about? Like 150% growth in your, your impressions or anything like that? Or is it just a whole world of difference that you just kind of know this?

Stephen: Yeah, it's, it's shifted almost, I should say, like almost everything in terms of what, what has back up. What has especially shifted is people's perception of really in the market.

And this is what I find really annoying about marketing is that it works. Right. So if I look at us, say prior to us posting on LinkedIn, for example, we were doing all the same stuff internally, right? We were shipping really fast. We were growing revenue fast. Inbound was growing.

All of these metrics were headed the right direction, but we didn't talk about any of it externally. So nobody knew. Now we share those stories live on LinkedIn. We talk about how revenues growing, inbound's growing.

We share customer success stories. We're doing more case studies now, like we're being loud about what's happening in a real estate doing feature releases. And now people are saying, Oh, wow, real estate has traction. Real estate is making an impact. Real estate is growing with customers. It's like, well, yeah, it's been happening this whole time, but we didn't talk about it.

Elijah: So nobody knew. And suddenly people care about you because you have feelings and you're talking about feelings that go, Oh, I'm paying attention. And of course the Sequoia move that helped.

You said you got a couple leads from that couple of new customers just from that big announcement. So kind of simple. I don't want to downplay you, but it doesn't take a lot. It just takes that grit and testing and kind of figuring it out.

Stephen: Yeah, that's, that's the funny thing is it's not, it's not complicated. It is hard in the sense of it. It requires consistency. It requires kind of determination. It requires a good level of creativity, especially to keep posting consistently on LinkedIn, but it's not hard.

There's so much junk content on there that if you just show a little bit of personality, you can do really well. And if you thoughtfully engage with people in the comments, I'll send people messages and the engagement content, you know, Hey, thanks for commenting. Great to connect. Hope you have a great week. Right. If you show up as a genuine person on the platform, there's almost nothing you can't do there.

Elijah: Nothing, including not being bothered about the post funding pressure, because always shareholders or investors want a little something, something, right? They always want their money back in some way. Do you have a particular focus or direction or do you just throw the dice? Like they do in Dungeons and Dragons or something like, whoop, I'm just going to make bet on this or this, depending on what I roll. Do you have a way to do things or do you just go, I'm just cool. I'm just even I'm going to do my thing.

Stephen: We'll continue in terms of like what comes next for real on the marketing side. We are all in on LinkedIn and that's both myself, our founder, even like across the company, like post-seeing, engaging our customers are on LinkedIn.

So like we are going to continue to be there as a company. The kind of second channel for us in terms of marketing is, is outbound. And what that means is not just kind of cold outbound outreach. But when I think about our roles, a marketing team in that is how do we enable the sales team to be successful in outbound? And that covers everything from from case studies and materials and including like what are the things we can do to make them successful there? And then finally, something that really has not really dabbled in yet. It's like Google ads.

I have no clue what to do there. I'm a finance guy, right? So we've we've hired someone who is just a real hustler and it's figuring out and going to get a setup to just really excel there. I think we are very under leveraged there as a company and we'll see some big dividends as we invest there.

Elijah: Here's hoping. And it's nice. You can't do everything because you're going to grow and and and become more and you're going to be louder if that's even possible. So it's nice to have even, you know, part time sidekicks here and there doing their thing or full time and you just kind of work as you go. Do you do focus more on one person that's full time or do you have a lot of fractional kind of contractors that help you out? We do both.

Stephen: And I we think I think a lot about how do we scale this team? And we've been especially focused on staying small. It allows us to stay nimble and switch things as we need to. And it keeps our costs low. Like I said, we are finance and accounting people first. So we are probably spending less money than we should. Frankly, we should probably be throwing more money into this marketing engine.

But it through things like LinkedIn posting, that's free and it works. All right. So we're going to continue to kind of go that direction. At some point, we should probably be doing more consistent blog postie, whether we hire someone full time or kind of outsource that. I haven't quite figured on our strategy there yet, but we are drowning in inbound.

It is not. It's probably 90% of our customers coming down to us. And it's it's because folks are looking for a different solution than the legacy providers. And I know as. A marketing leader here that will not last forever.

Either it will, you know, as the kind of early adopters kind of peter off that will get harder for us. And so my kind of top priority as marketing leader is how do we continue to grow this inbound engine within really what are the other levers and other channels we can be looking at to grow this business.

Elijah: Anything top of mind that you're really thinking besides the freebies and the paid that you're trying to get help with, or you just want to invite everybody to, I don't know, let's pick a roller coaster. Let's go to Six Flags and just hang out for a couple hours and then invite everybody and have fun at steak dinner.

Stephen: That would be a fantastic event. I would love that. I'd go to that for sure. We're definitely gonna keep doubling down on in-person events. In-person events have been fantastic for us.

I've hosted 15 dinners in the last nine months. If you're gonna host an in-person event, you need to make it very thoughtful. And you have to approach it with care to make it good. Folks are sacrificing their time away from work, away from family, away from personal to come to this corporate event. It should not be boring.

It should be interesting and helpful and useful for folks. So that's kind of the dinners that we build at Rillet. But in terms of just raw marketing dollars, those have been incredibly high ROI for us. Nearly every dinner we sign a customer, whether two months down the line or six months down the line. And we just build incredible relationships in person that you really can't replicate otherwise.

Elijah: If I may point back to a previous episode, not too long ago, there's a lady named Chrissy who is great with startups and marketing, but she is a big F1 fanatic. So she took an event, took the next level and just booked a whole go-kart track for like a two-day thing and then had people there. And the fun part that she didn't realize was you get all those conversations and just people chatting because they're having fun, they're there anyway. And they just like, oh, what do you know about this? And then you just kind of groove and vibe, which is kind of neat. So you have one nearby, I totally suggest that.

Stephen: I would just like considering hosting a poker night in New York in a few weeks. Because I agree that the best part about events like this, it's really, if I'm honest, like A &M has a vendor selling software, they're not coming for me. They're coming for the peers they get to connect with. And that's really the difference is they wanna know who else is gonna be at that dinner and who can they add to their network? And not just for their careers, but they're all dealing with problems, right? The last year we had one of the CFOs shared a problem with the table and said, hey, I'm having trouble, you know, connecting with my investors in this way.

I need this from them. How would you approach this? How would you do it? And around the table, folks shared, you know, what they did in prior circumstances, what worked for them, what didn't work.

And the CFO left with a playbook for what he could do. Like that's the power of these things. It's not, like that's something that we get to create a software vendors for people.

Yeah. And why people come to these things. If the point of a dinner is just to pitch the software and nobody wants to come to that, that's not fun. That's not engaging.

Elijah: It's kinda cool because even if it's not a direct ROI or a lead or a sale from that, the memories and the experience that you've created to be top of mind, you're like, oh, Stephen did this. This was really cool. You should check out his company.

Like even that word of mouth organic play and additional kind of compounding ROI. Amazing. Even if it is poker and a CFO is going, I wanna be a bit selfish, go ahead, please. If you get something out of this that's not unexpected, then that's the whole chaos theory in action. It's nice. Exactly.

Stephen: The annoying part about that is it breaks my brain as a finance person. Wow. As a finance person, I went direct ROI for that dinner. All right, I wanna be able to tie clear that we signed this customer X many months later. And that often happens for us right now. I know it won't happen forever.

And it's also okay if it doesn't. There is a brand that we want to build as a company, as helpful folks in this space, as a company that wants to push the profession forward as a whole, not just build cool software, though we are doing that as well.

Elijah: I wonder how many people would be annoyed if you gave them a Q card with the details and then a QR code saying, hey, would you mind filling a quick survey? And then you get that kind of customer insights, but they just want the poker and the drinks. So it's kind of a nice trade-off to not piss people off, but to also get that information. So that's your problem. Lucky.

Stephen: This is where LinkedIn can become so powerful. True. Is I can invite folks to an event, meet them at the event, connect with them on LinkedIn afterwards. They continue to see my content and we become friends. Right?

That makes a difference. You can't do that without having, otherwise the only way you engage with them is with newsletters or some trip campaign, or which is fine. I think that can work for a lot of folks, but the beauty of doing B2B marketing today in this social age is that I can connect with folks at events, connect with them on LinkedIn and keep them in the really kind of ecosystem. So when they're ready to make a purchase for their ERP, they know where to go.

Elijah: Hopefully, as I explore this lovely marketing journey that I've recently just started, maybe I'll be able to refer and help out, but for now you just tolerate all the crazy, goofy ideas that come randomly in your DMs like, hey, Steven, what do you think about this?

Ooh, I like that. I'm going to go try that. I think I got a couple yeses from you. I'm going to try it. So I call it a win. We're good. We're doing all right.

Stephen: I call it a win. They've been great ideas. So keep them coming.

Elijah: I will. Can we go back to the first week at Rillet? Maybe give yourself one piece of advice. You know, the old 20 years ago, I could do this. There's got to be something you're like, what would I do? I'm perfect. I would do nothing wrong. Done. Is that where we're at?

Stephen: Absolutely not. If I can go back, the honest answer is I think I tell myself it's all going to be OK. Oh. In that I am the type of person that stresses out a lot in high pressure situations. And when you're in a startup, especially this early stage, everything feels high pressure.

At the time when I joined, I think there were 15 of us. So I'm basically, it feels like I'm carrying 5% of the company on my back. It's not really true, but that's kind of what it feels like.

And there's some reality there. So every customer call feels hyper important. Every partnership call, every feature release, every little thing feels like this will make or break the company. And it's not quite true.

Right? There's some truth there. But the reality with building a startup is we think that it's all these single opportunities that make or break. And looking back, you see that. You signed this one customer.

You made this one deal. You released this one feature, whatever it was. But when you're in it, it's not like that. When you're in it, you have 10 opportunities with 10 different high-profile customers. And you get one. And that becomes your anchor to get the next one and get the next one and get the next one. So yes, every interaction matters a lot. And also, the stress that I attach to it, it's fine. Everything works out. So if I could go back and tell myself, I tell myself that a lot even now, that everything is fixable. There is grace. There is space. It's much better to hustle and work with care than to stress out about all the little details.

Elijah: Funny enough, as a high function creative, whatever you want to label that is for me, I overthink at a nauseating level. So I get that. But I lean into the pressure because I just kind of do as a bias to action without really thinking about the consequences. And that has its own risk.

But that really resonates. And even in two weeks in into my role, I'm a contractor. I used to be in corporate where there was that salary that was false feeling of a safety net. And now I'm like, they could leave me tomorrow. So I need to provide that value or I'm out. But they're like, you're doing a great job.

Shut up and just do it. So I think it's kind of a nice little moment to resonate with because you're not the only one, especially if you're getting an influx of inbounds and a wait list, apparently. It's just showing up on LinkedIn and saying, hey, we don't want to spend all of our money because we're accountants. And everybody's like, I love you. It's easy. I don't know.

Stephen: I wish it was that easy. It feels that easy some days. And some days it feels the opposite.

Elijah: I'll just keep telling you that everybody loves you. Maybe I'll record a GIF or something just fired off on your DMs every day and see what happens. Who knows? That would be great. At least I can amuse you. That's what I'm here for. So that's good.

Stephen: But I think if those of us that work in startups are more honest, it's hard. It's really hard. And it's also very rewarding. It's really fun. I've never had as much fun in a prior role.

I can't believe I get to do this every day. And it's also incredibly hard. It's hard on myself. It's hard on my family.

I have two very young kids. And working in startups is hard because it's the only way to be successful is pure hustle. It is just knocking on as many doors as possible, going as fast as you can. Like there is no, when I was young, I thought startups were very sexy. I read about Jeff Bezos and Travis Kalanick and all these leaders when I was in high school. Oh my god, man, that sounds so fun. I want to move to Silicon Valley and do that. And now in many ways, I'm kind of living what I wanted to as a kid. If I had known it would be this hard when I was 15, I would never have tried to do this.

Elijah: Is that what it looks like on the outside? It's easy, peasy, it's sexy, it's fun. It's Jeff Bezos or Bill Gates or whatever. And on the inside, you're saying it's hard. Is there anything else? Not like that's obviously a big one, but is there anything specific that you go looking in on the inside, somebody would really get it? What really happens?

Stephen: Yeah, it's hard to know until you're in it, frankly. Like we can tell even like people joining, really like, hey, this is hard. This is long hours, this is a grind, this is really fast paced. But until you actually get into the company, into the role, it's hard to tell. I've talked to a lot of folks who say, I want to work at a startup. And some of them are right, and some of them don't know what it means to be at a startup.

It is very different. The story that I often tell of working at a startup, I started at Walmart. And at Walmart, we had entire teams that owned our data and owned our reporting.

When I joined my first startup, we are like series C had about 150 people. And the data was there. I had to build my own reports and everything, but the data existed. Now at an early stage, seed startup, there is no data.

Elijah: And then you're trying to quantify that to get the series A play or the private VC. There's no data. It's all indirect attributions as we've learned. And now I'm just trying to figure out how the hospital works. Maybe it's a QR code, maybe it's a steak dinner. Hey, I've had 50% of whatever leads or something from steak dinners. Wanna buy us? And like, what are you talking about? It's difficult, absolutely. Yes.

Stephen: And you kind of have to be okay with that at this stage. If you wanna work in a startup and do it this early, you have to be okay with not knowing everything.

And sometimes, I don't know if I should say like you need to be able to go with your gut, but you have to be able to trust your intuition and move quickly.

Elijah: So is it like jumping out of a plane every day? Is that kind of what I'm getting? Or is it not that crazy?

Stephen: It's almost worse. Really? Yeah. Oh.

Elijah: Like, it's like, what's it at 10,000 feet in the air? Like, I don't know what's happening, maybe?

Stephen: I don't know, maybe like two months in, two months into my role at Rillet, I was freaking out about all these different things we had going on internally. And my boss kindly told me, he's like, hey, there's fires everywhere all the time. The important thing is knowing which fires to prioritize, which ones you can tamper down and then move on to the next one. There's always fires. I could spend hours, even now, making sure like our marketing reporting is better, our lead funnel is better.

Like all these, I could spend all this time doing that. That's not gonna push the needle forward for us. Right? I need to be spending my time on things that actually drive Rillet forward and make a difference for the business and putting out those fires. And once those are out, then I can move to the next one.

Elijah: Those important things are talking about memes, right? Exactly. Lots of memes. The fire, everything's fine, it's burning. That's Steven's job every day until we kind of get concrete and putting out the fires. Why don't B2B traditionally go for the funny stuff, the human like the, I know sometimes there's bottom feeder stuff that happens on social media, but we're all human beings who wanna avoid working for 10 minutes, I'm going to scroll and Steven needs to entertain me. Is that where you're going with memes?

Stephen: Yeah, I think about memes, I guess, in a couple of ways. We don't post any memes from our corporate account. They don't work very well. Interesting. Any memes that we post come from me. I think that works better to have it come from a person rather than from a corporate account. So there are some corporate accounts that do it really well. HubSpot, posts a lot of memes, Ramp post a lot of memes, and it works for them and for the brand.

Maybe it will be there someday, but we're not there yet. I think it works better coming from me because it fits my personality a bit. And I can do kind of like stupid things with the memes that work for myself and work for our customers and target market, frankly. It would be hard to say for our CEO to post some of these memes. It just doesn't fit his personality. Hearing it from a founder might be a little odd, right?

Some founders do it and do a really good job of it, but it's difficult. I think memes are harder than people think. You should respect the meme a little more.

Elijah: It's got to be honest and true to you. You can't just throw out something that has to do with, I don't know, something that's not in your wheelhouse. You're going, is this guy okay? Did he take his medication today? What's wrong? You all right, buddy? Exactly.

Stephen: And the meme should be really funny. It should not just give you a little chuckle. It should really crack you up. I should be falling out of my chair. Yeah, that's the meme you want to do.

Elijah: Yeah. I think that we got a rough idea of what goes on in the startup world, how finance treats marketing. So we talked about startup. We've talked about you flying out of planes and doing all crazy stuff and then putting the world on fire mentally with the memes.

Of course, you don't want to really do that because that's dangerous. You're more than a head of finance. You're more than a marketer. You're more than a guy that does the merch and is loud. Is there anything outside of work, Steven, that brings you joy?

Stephen: I am a dad. I have two kids, one boy, two and a half, and girl just turned seven months yesterday. It is the best thing in the world. Yeah? I love being a dad.

Elijah: Some people think they're pain in the rear end, but I guess they are.

Stephen: They are, they definitely are. There are days I was, you know, how do I say this in a way that's public? I shouldn't say there's days. There's times, you know, kids are very frustrating.

Elijah: It is, and you got to live with each other. Every single day, they don't choose to come in this world. You're like, I'm just Steven, I'm cool. I'm going to teach them that startups are going to be okay. It's going to be okay, kids. Going to do it. It's going to be fine. Exactly.

Stephen: But there is, oh man, there is nothing better than when my son gets home from daycare and comes knocking on my office door and wants to come in and comes in and just gets me a big hug. It's like, it's the best feeling in the world.

Elijah: Put on some work merch, play with the John Deere in the background,

Stephen: whatever it is, have a good time. Yeah, yeah, exactly. And it's funny, my entire perspective on work shifted when we had kids in that I don't just do it for myself anymore. No. I do it for them. I want my children to see their dad working hard. I want them to know that hard work makes a difference that you can do whatever you want, but it takes work.

I also want them to know their dad is present with them. I try to never work on Saturdays. That's like my time especially to be with family. And then I'm also very guarded on between when, the work day is done, when they go to bed. I try, right?

I'm still often on my phone slacking sometimes, but trying to be like present with them in those moments because that's what matters. Absolutely. This work stuff really could explode tomorrow, right? Or like even if I, I hope I can be at Rilla for the next 10, 20 years, but I'll be a dad for the next 60 at least.

I don't know how long I live, right? So that's what matters is being a parent. And that's what I have the most fun doing. You often see if you follow me on LinkedIn, my son makes it into my LinkedIn posts very often. I affectionately call him my accounting intern and make jokes about his Excel skills or lack thereof or whatever.

But it's fun. I love that I can be public about being a dad on LinkedIn and on social. I've had dads reach out to me directly on LinkedIn and say, hey, I really resonate with your post. I feel the same thing about working in tech and with kids. And it's been such an incredible point of connection where in some ways like I'm just doing like dumb posts on LinkedIn about being a dad and other times and doing a very serious and genuine post of being a dad, right? But I think we all are looking for connection and looking for folks to say the things that we're nervous to say. And if I can be like a light for someone a little bit on LinkedIn through my posts, like that's success, right?

Elijah: And tell us kind of what's going on in the world and where we can find you to experience the meme-tastic magic.

Stephen: Yes, you can find me on LinkedIn, other show notes. You can follow me on LinkedIn. That's where I do all my memes, accounting, AI and dad posting. I think the link for my profile will be in the comments. Otherwise you can find us on the realit.com. We're building the AI native ERP, the future of finance and accounting. Come check us out.

Elijah: Right on. In the comments, the podcast description, all of the things will make sure it's out there and make sure you get the recognition so people know where to go to experience all Steveness and Rillet.

If you love this conversation, I have two other episodes that tie in nicely. There's a guy, Mike Moreno. He's with RevGen AI. He's talking about the playbook and early stage companies, nail their GTM strategy and leveraging AI just not for the hype, but for reals and scalable growth. Also, Margie Agan, she's with center board marketing. She breaks down how to craft messaging that converts enterprise buyers kind of similar to Rillet's ICP and those will be in the description too. Tea time with tech marketing leaders powered by MKG Marketing. We manage the details. You capture the market. I'm Elijah and I'm way too sexy for this microphone. I'll see you soon.