Culture is a foundational component of business strategy

From day one, Bilt treated culture not as an afterthought but as a business imperative. Even when the company was small, O’Sullivan and leadership ensured every employee received benefits, 401(k) matching, and clear communication. They recognized that meeting basic human needs builds trust and loyalty—an especially important lesson for startups scaling fast.

“Everyone had to have an offer letter. Everyone had to have health benefits… basic human needs were taken care of.”

Intentional, high-touch onboarding can make an impact

Bilt designed a custom 90-day onboarding program for each employee. Managers create personalized plans with clear project ownership so that by day 90, every hire has made a tangible contribution. The process culminates with a “Bilt Letterman jacket” —a physical token of belonging and pride that reinforces cultural identity and recognition.

“By day 90, your fingerprints should be on something… We give everyone a Bilt Letterman jacket as a physical symbol of being part of something bigger.”

Scale with purpose, don’t get overly concerned with headcount

O’Sullivan emphasized resisting the common startup temptation to equate funding with rapid hiring. Every headcount at Bilt must be justified. Leaders are asked: “Do you really need this person? What will their impact be?” This thoughtful approach preserved culture, avoided team dilution, and maintained operational focus.

“Funding coming in does not equal headcount… We were intentional about who we brought in, when, where, and why.”

The human POV is an advantage in the age of AI

Rather than fearing AI, Bilt embraces it through experimentation and education—they even shut the company down for 48 hours to explore AI tools. Yet O’Sullivan’s message to HR peers was clear: the rise of AI makes human connection more valuable than ever. The ability to build relationships, communicate empathy, and collaborate in person is now a differentiator.

“It’s more important than ever to be human—to shake hands, make eye contact, and connect.”

In-person work can be a competitive advantage for scaling teams

While many companies went hybrid or remote, Bilt stayed in-office from the beginning, rooted in trust and collaboration. The company’s “be an adult” policy allows flexibility for personal needs but assumes accountability. O’Sullivan argues that in-person interaction builds trust, accelerates decision-making, and drives innovation—especially in complex, cross-functional teams.

“Trust and collaboration have become our competitive advantages because we can move quickly.”

Creating a safe space for experimentation pays off

Bilt’s people team fosters a culture of curiosity and psychological safety. Whether in AI experimentation or employee development, failure is reframed as learning. The company encourages employees to “teach us about your failing.” This attitude fuels innovation and builds adaptability—skills critical in today’s rapidly changing environment.

“Be curious, experiment, and if you fail, have fun and teach us about your failing.”

The role of the people leader is being redefined

O’Sullivan sees the modern people leader as a translator, curator, and human enabler—not just an administrator. The job is to help humans adapt and thrive amid rapid change, bridge executive vision with day-to-day reality, and curate the right tools and processes to empower teams.

“Our job is helping humans adapt and thrive in a rapidly changing environment… HR has evolved into being the translator between vision and reality.”

A call to action for HR and people team leaders

Her final message was blunt but energizing: companies that block AI experimentation are holding their people back. Just as email or Google once transformed work, AI literacy is now essential for staying relevant.

“If your company isn’t letting you use AI, you have a decision to make. You’re going to get left behind.”