The art of hiring: insights from Khosla Ventures, Airbnb, Ramp and Traba

November 26, 2024

The art of hiring: insights from Khosla Ventures, Airbnb, Ramp and Traba

Fiona LeeFormer Content Lead, Ramp Luke O'NeillContributing Writer

Keith Rabois knows a thing or two about building winning companies. He’s the Managing Director at Khosla Ventures, and Ramp's first institutional investor. He’s known for his legendary investments (Stripe, DoorDash, Affirm, Faire) and pivotal executive roles (Paypal, LinkedIn, Square).

With credentials like that, it’s no surprise founders seek his advice. The one piece of advice he’s given countless times to countless leaders? Don’t overlook the importance of smart hiring. It can mean the difference between high growth and failure.

In fact, this wisdom is so vital that Keith and Khosla Ventures recently hosted an entire day of talks on the topic. Ramp CEO Eric Glyman, Airbnb’s Brian Chesky, and Traba’s Mike Shebat joined Keith to share their experiences and lessons learned.

Keith Rabois: Founders, stay hands-on in hiring

Keith kicked off the event by discussing the high bar founders should set for startup hiring. "The most important advice I’ve gotten in my 23 years of working in tech was from Vinod Khosla," he said. "He said to me, ‘The team you build is the company you build.’"

"The team you build is the company you build." – Vinod Khosla

So how do you attract the right talent? A few of Keith’s most contrarian views:

Don’t hire the obvious people. They are being courted by the likes of Google and startups don’t have the financial resources to compete. Instead, pursue—and attract—undiscovered talent. Develop a compelling pitch: if your company is an upcoming blockbuster movie, what would you include in its trailer?
Scout everywhere. Keith urged founders, "In a hot market, find talent wherever you can." Hire interns who have the potential to be the next Zuckerberg. Hire founders and articulate business problems that are so interesting that they stay on for years. Look for people who take risk in unconventional ways and can "positively manipulate the world around them."
Be the team arbiter. Too often, founders make the mistake of delegating hiring to managers who are inexperienced at hiring. During Square's early days, Keith and CEO Jack Dorsey personally interviewed the first 400 employees to ensure a high caliber of talent. Keith noted, "Being great at your craft is not the same skill as assessing a stranger that walks in the door."

To build a winning team, founders and CEOs have to be willing to invest the time. Keith goes into how leaders should run interviews, gather references, discern when to hire versus promote, and more. See his full talk here:

Eric Glyman: Seek out super individual contributors (ICs)

At the event, Eric shared Ramp’s recruiting playbook and how we’ve attracted atypical talent, including 70 ex-founders. Our hiring philosophy boils down to two principles: 1) find deeply talented people who spike in specific areas (aka super ICs), and 2) give them the tools to be exceptionally productive.

When you combine these two tenets, the result is velocity at scale.

"Find people who have craft in their work and thinking." - Eric Glyman

Here is Eric’s top advice on attracting super ICs:

Know what you're looking for. The best sushi chefs start their career tasting sushi, not making it. That’s how they develop world-class taste. Similarly, before founders and leaders hire, they need to own a perspective on what excellence and good judgment look like for the role they’re trying to fill.
Favor the craftsmen. Hiring managers often assess candidates based on the companies on their resume. This is a mistake. To build talent density, see if the person actually created the work at the companies you admire. "Find people who have done the work, sold the deals, written the copy, designed an interface," Eric said. These are the people who will attract others with similar standards.
Assess for slopes and spikes. In a competitive hiring market, take a page from the Moneyball playbook and look for mispriced talent to maximize return. Ramp is filled with high school dropouts, competitive math champions, and Minecraft whizzes. Their common attribute? High growth potential over initial skills. "Write unreasonably short job descriptions and make it easy to assess performance on one metric," Eric advised. "The goal is not zero defects."

To hear how to scale hiring as you grow, watch Eric’s talk here:

Brian Chesky: Find your founder mode

Recently, Airbnb CEO Brian Chesky gave a talk on founder mode that went viral. It challenged longstanding thinking about company leadership. At the event, Brian fleshed out his provocative perspective in a fireside chat with Keith:

Have as few employees as possible. A few years ago, Brian noticed that Airbnb was slowing down. An overabundance of sub-teams and general managers imposed a "communication tax" that caused excess meetings, internal politics, and ultimately C-players. Brian ruthlessly eliminated management layers and now Airbnb runs more like the Navy Seals: small, elite, highly skilled groups where leaders focus on managing the work first, not people.
Leadership is presence, not absence. A common management adage is to hire great people and trust them to do their job by giving them space. Brian challenged the idea. Leaders who don’t dig into the details have no insight into the actual work quality. At AirBnB, regular CEO reviews of all customer-facing work ensure a cohesive product vision. "Anything a customer experiences, I see," Brian shared. "If I don’t review it, it doesn’t ship."

"Be in the details. Leadership is presence." - Brian Chesky

Recruit outside of job openings. Too often, founders approach hiring as a sales pipeline rather than a networking activity. Instead, they should constantly ask who’s doing the best work and spend as much time on references as they do on interviews. "You need evidence to hire people, not to eliminate them as a candidate," Brian reminded the audience. "When companies get this wrong, they end up hiring mediocre people."

Watch the full conversation here:

Mike Shebat: Change gears for growth

Mike Shebat, the CEO of Traba, an industrial staffing solution that is reinventing the global supply chain, took the stage with insights on how founders can maximize the productivity of their star players once they’re in the door. It takes just a couple of bad gears in a fast-moving company to grind the team to a halt.

"You’re the leader. Orient the gears." - Mike Shebat

In Mike’s experience, founders can grease up the gears in these ways:

Focus on force-multiplying work. Be crystal clear about where the company is going and what needs to happen. Push back on passion projects. This advice may seem obvious, but Mike emphasized, "You have to be a broken record about your vision because there are new people joining constantly and people who are so ingrained in their craft. You've got to cut through the noise and keep reiterating yourself."
Learn the art of not hiring. Mikecautioned against the impulse to expand rapidly. In a resource-constrained environment, first ask how you can be more effective with the people you already have. Stamp out poor behavior (e.g. being late to meetings, exceeding per diems) before it spreads across your team and deters productivity.
Prevent future rust. Once you’re ready to hire, look for force multipliers who can dream big and are up to the task. When they hear about your company’s vision, do they ask "how" instead of "if"? Are they realistic about what the work will entail? Mike shared, "I actively anti-sell candidates: 'We’re in the office late at night. We work every day. We’re always online.'" Doing so filters out people who are not ready for the journey.

In his talk, Mike shared more strategies for building winning teams:

Like what you hear? Check out our job openings: https://ramp.com/careers

Fiona Lee•Former Content Lead, Ramp

Fiona writes about B2B growth strategies and digital marketing. Prior to Ramp, she led content teams at Google and Intercom. Fiona graduated from UC Berkeley with a degree in English.

Luke O'Neill•Contributing Writer

Luke O’Neill is a freelance finance writer and content strategist, with deep experience in B2B fintech and financial services. His work has appeared in The Wall Street Journal, Bloomberg, The Irish Times, the Stanford Social Innovation Review, and more.

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