The Load-Bearing Team Member: How Check Built a Culture Where Everyone Moves the Needle

"There's no job too small for anyone in the company to do," says Andrew Brown, CEO and co-founder of Check, describing why he still ships code alongside his 100-person team. "I think it's actually by doing that work that you learn how to be really great at designing the bigger picture solution."

Brown isn't performing CEO theater. This hands-on approach reflects the foundational philosophy behind Check's culture: building a team of exclusively "load-bearing members" where every hire genuinely moves the business forward.

Why Work Here is a series in which Amit Matani, CEO of Wellfound, has honest, behind-the-scenes conversations with founders, executives, and employees about why their companies are worth joining.

Check occupies an unusual position in the payroll landscape. Rather than competing with established players like ADP for direct customers, they're rebuilding the entire industry as an API-first infrastructure provider. Traditional payroll companies sell bundled services directly to businesses. Check powers the all-in-one platforms that modern companies actually want to use.

"We think payroll today is fundamentally broken," Brown explains during his conversation with Amit Matani, CEO of Wellfound.

"Historically, you went and signed up for a payroll company and they'd give you HR and all these other services. Today, most likely, you're signing up for an all-in-one platform to power your business, and you want that platform to do everything for you including payroll."

This infrastructure approach has become a powerful talent magnet. Engineers at Check aren't optimizing conversion funnels or A/B testing button colors. They're rebuilding fundamental systems that move tens of billions of dollars and ensure millions of Americans get paid correctly every pay period.

The Problem That Attracts Obsessive Nerds

Brown describes Check's culture in three words: intensity, deep caring about partner success, and "nerding out about the details of the payroll industry." That last point might not sound glamorous, but it's precisely what draws their ideal candidates.

"The best people are attracted to hard problems, and in our case that means payroll. It's moving tens of billions of dollars around, ensuring people are getting paid every single day. Really what Check is building at the end of the day is a utility—a utility that is in the future going to be the way that every single person in this country gets paid."

Unlike consumer startups that require endless A/B testing to find product-market fit, Check operates in a world of regulatory specifications and clear requirements. Pennsylvania mandates tax calculations work a specific way. The government provides detailed compliance frameworks. The challenge lies in building modern, scalable systems around century-old industry practices.

"In fintech, especially, a lot more of it is, here's a regulatory spec from the government you have to follow," Brown notes. "It's really more: how can we take these really big old industries that have been around for 100 years and build them in modern ways? That's just a totally different type of problem to solve and attracts a different type of person."

Why Load-Bearing Members Matter More Than Team Size

The concept of "load-bearing team members" emerged from Brown's observation of how most startups gradually dilute their talent standards. Early-stage companies start with everyone being essential, then slowly allow that bar to slip as they grow.

"I think most companies lose that as they scale," Brown reflects. "You hope for it, but then you don't hold the bar high enough. You don't let go of the bad apples that you need to. So you just end up in a culture that's consistently watered down over time."

Check took the opposite approach. At 100 people, they've maintained the expectation that every new hire will tangibly change the company's trajectory. It creates what Brown describes as productive tension—the knowledge that your work genuinely matters.

"You are going to be a load-bearing member of the team full stop ... There's no one on the team who isn't. That can be a stressful place to be, but I think it's a really exciting place to be too, because it means you are going to have an impact."

This philosophy extends beyond hiring into daily operations. Team sizes for any shipping project stay under 10 people—smaller than Check's entire company in the early days. The constraint forces clarity about priorities and ensures individual contributions remain visible.

Seeking Truth in a Consensus-Driven World

One of Check's core values—"seek truth, not consensus"—might sound like corporate speak, but Brown takes it seriously. The company deliberately hires people willing to challenge each other and push back on ideas, even when it creates uncomfortable moments.

"We're not afraid to challenge each other," Brown explains. "We want great people who are going to come and tell each other that they're wrong and push and figure that out."

Making this dynamic work requires careful expectation-setting rather than hiring people with particularly thick skins. Brown draws parallels to family relationships where conflict serves a constructive purpose.

"If you've ever been part of a family or part of a long-term relationship, you argue with those people. They're not always right. There is conflict. When you root it in a sense of mutual respect and admiration and caring for each other, that actually raises the level at which you can disagree and be really direct. It's almost like a form of caring and investment in one another."

The approach reflects Check's belief that the best solutions emerge from rigorous debate, not comfortable agreement. In an industry where compliance mistakes can cost millions, getting to the right answer matters more than preserving feelings.

The High-Agency Hiring Filter

Brown is refreshingly candid about traditional interviewing limitations: "I think interviews are borderline useless. Like, it's so hard to get good signal from them."

Instead, Check focuses on identifying "high agency" candidates—people who have consistently changed the direction or pace of their previous companies. They screen for three traits: high agency, strong work ethic, and an entrepreneurial, optimistic mindset.

The real differentiator happens before formal interviews begin. Most candidates approach the process passively, showing up ready to answer questions. The ones who stand out demonstrate genuine investment through research and preparation.

"A lot of people show up and they're like, 'hey, this is me, I'm gonna answer your questions,' which is fine," Brown notes. "But to really stand out, put in the work."

That work includes sending personalized emails explaining specific interest in Check's mission, arriving with five concrete ideas for potential impact, and asking provocative questions about company strategy.

"Not very many people do that. When you're interviewing with another engineer or PM, come with interesting, provocative questions about what our strategy is going to be. It's that kind of stuff that makes you really stand out from the crowd."

The approach filters for candidates who think like owners rather than employees—exactly the mindset Check needs for load-bearing team members.

Remote-First, Connection-Intentional

While many startups have reversed course on remote work, Check maintains a distributed approach with a structured twist. They believe in both hiring great people and bringing them together regularly for relationship-building and difficult conversations.

"People think that if we just get everybody in one room and they're there every day, that will be successful, and you lose—what is the implication of that for having great people?" Brown asks.

Check's solution involves offices in New York and San Francisco, where local team members work several days weekly, plus a structured rhythm of connection: quarterly travel for everyone, annual company offsites, regular department gatherings, and smaller team meetings.

The company takes different approaches based on group size and purpose. Leadership team quarterly sessions focus on working through the hardest business problems together for 12 hours straight. Full company offsites in places like Mexico balance business updates with relationship-building and fun.

"We've really tried to strike a balance," Brown explains. "Pretty much everyone in the company is traveling at least quarterly to get together. I think that's a core part of how we've made things work."

The Post-Product-Market-Fit Recruiting Advantage

Check's position past product-market fit creates significant recruiting advantages. They offer something many startups can't: proven demand combined with meaningful individual impact.

"We're a team of about 100 people...That means we're big enough that you know what to do. We're past product market fit. Our customers are always asking us for more things. But we're also small enough that every single person that joins, I know exactly the ways in which we're expecting them to really change the trajectory of the business."

This sweet spot eliminates much of the uncertainty that makes startup recruiting difficult. New hires join knowing there's real customer demand while understanding their contributions will visibly move the business forward. The combination attracts candidates seeking both stability and impact.

The company's embedded approach also means they're selling to other founders, engineers, and entrepreneurs—creating an additional feedback loop with smart, demanding customers who push the team to improve.

Building Infrastructure for the Future

Check's talent and culture approach reflect their long-term vision of becoming the utility that powers American payroll. That infrastructure play requires people capable of thinking both big and small: envisioning industry transformation while debugging customer integrations.

"What Check is building at the end of the day is a utility," Brown emphasizes. "It's a utility that is going to be the way that every single person in this country gets paid in the future."

The vision attracts what Brown calls "obsessive nerds" willing to dive deep into payroll regulations while building modern, scalable systems. It's not glamorous work in the traditional startup sense, but it's consequential work that affects how millions of Americans receive their paychecks.

For candidates considering Check, Brown's message is clear: come prepared to be genuinely load-bearing. The infrastructure of American payroll is being rebuilt, and they want people obsessive enough to help build it right.

Final Tips for Founders, Recruiters, and Job Seekers

Founders — Maintain your talent bar by clearly defining what "load-bearing" means for each role and refusing to compromise during rapid growth—most companies accidentally dilute standards over time.

Recruiters — Hunt for candidates who demonstrate genuine investment through research-backed applications and tailored ideas—they're signaling the high-agency mindset that top companies desperately need.

Job Seekers — Stand out by arriving with five specific ideas for impact based on deep company research, plus strategic questions that show you're thinking like an owner, not just another employee.

Watch Check's Why Work Here episode on YouTube and Spotify and view Check's open jobs here.