Matt Schulman didn’t just build Pave—he rewrote the playbook on hiring. Before his company helped thousands of businesses manage compensation, he had to master one thing: recruiting the right people at the right time.

It wasn’t a conventional process. Schulman, the founder and CEO of Pave, didn’t rely on traditional job postings or recruiter pipelines. Instead, he crafted a hiring strategy that combined contract-to-hire testing, deep personal investment in candidates, and radical transparency in compensation.

The result? Pave now boasts 160 employees, 3,500+ customers, and a $1.6 billion valuation. Here’s how he did it—and what founders can learn from his approach.

Hiring as a Two-Way Street: The Power of Contract-to-Hire

Early on, Schulman knew that resumes and interviews only revealed so much. To truly assess a candidate’s fit, he introduced contract-based hiring. Instead of making immediate full-time offers, he brought top talent on as contractors first—letting both parties test the waters before committing.

The strategy worked.

“I had a 100% close rate with the candidates we wanted to convert to full-time,” Schulman recalls. By the time the contract period ended, candidates had already built relationships with the team, seen the company’s mission up close, and felt invested in Pave’s success. The transition to full-time became a natural next step.

For founders looking to replicate this, the key is positioning: Schulman framed contract work as a mutual evaluation process, not a risk. He ensured fair compensation, gave candidates meaningful projects, and remained flexible—allowing those with full-time jobs to contribute on nights or weekends.

The First 10 Hires Can Make or Break You

In the early days, Schulman took personal responsibility for hiring. He didn’t rely on inbound applications. Instead, he sourced talent himself, met candidates over coffee or long Zoom calls, and evaluated their hunger and adaptability firsthand.

His focus? Generalists over specialists.

“The first 10 hires had to be adaptable. They needed to wear multiple hats—engineering, sales, operations—whatever was necessary to push Pave forward,” he says.

For founders, this underscores a key lesson: Your early team isn’t just about skill sets—it’s about mentality. Hiring people who embrace ambiguity and growth ensures a company can pivot, iterate, and scale without being boxed into rigid roles.

The Google Doc That Closes Candidates

Great hiring doesn’t end with an offer—it’s about convincing top talent to say yes. When Schulman encountered hesitant candidates, he didn’t let the conversation die. Instead, he introduced the “Collaborative Google Doc.”

It worked like this:

Throughout the interview process, Schulman created a shared document outlining what success at Pave would look like for the candidate.

The document evolved with feedback from both sides, detailing the candidate’s growth trajectory, expectations, and Pave’s commitment to their career.

By the final stage, Schulman conducted a 360-degree review, gathering insights from at least 10 people who had worked with the candidate before—then shared that feedback directly.

The result? Transparency, trust, and an offer that felt like a partnership, not a transaction.

Compensation Shouldn’t Be a Mystery

Pave’s entire business revolves around compensation transparency—so Schulman built the same principle into his hiring process. Every offer was detailed and data-backed, including:

1. Salary bands
2. Role levels and expectations
3. The methodology behind stock options and vesting

For founders, this is a crucial takeaway: Compensation clarity isn’t just ethical—it’s a competitive advantage. When candidates understand what they’re getting and why, they’re far more likely to commit.

Speed and Urgency in Hiring

To maintain hiring momentum, Schulman introduced private Slack channels for every open role. These channels kept all stakeholders aligned in real time, ensuring quick decision-making and constant movement.

He also refined outreach with a simple but effective follow-up strategy. If a candidate didn’t respond, his team sent a short, third follow-up email: “Hey, any thoughts?”

It worked. Sometimes, closing a hire isn’t about a grand pitch—it’s about persistence and keeping the conversation alive.

The Right People at the Right Time

As Pave scaled, Schulman learned that the best hires evolved at different stages:

1. Early days: Generalists who could thrive in ambiguity.
2. Scaling phase: High-growth "slope" candidates—those with upward career trajectories.
3. Mature company: Experienced executives who could manage complexity.

One crucial insight? Never rush an executive hire. While early-stage roles needed urgency, Schulman found that forcing a leadership hire to meet an arbitrary deadline often led to regret.

Blueprint for Founders: Schulman’s Recruiting Playbook

Schulman’s approach wasn’t just about hiring—it was about building a company with purpose. Here’s what founders can take away:

1. Test before you commit: Use contract-to-hire models to evaluate fit without long-term risk.
2. Invest in candidates personally: Create clarity in their career trajectory before they even join.
3. Be radically transparent in compensation: Trust is built when employees understand their value.
4. Move fast, but be deliberate: Hiring speed matters, but the right people are worth the wait.

Pave’s success wasn’t just about a billion-dollar valuation—it was about assembling a team that could make it happen. Founders looking to build their own empires should take note: Recruiting isn’t just a function. It’s the foundation of everything.