About First Round

First Round is a venture capital firm that works with founders exclusively at the earliest stages of company building, often when all they have is an “imagine if.” We fill in where we can until the team is filled out, tackling crucial early hiring and equipping those who are great at building product with the skills to sell it, too. By getting the foundational firsts right, we increase the odds of finding extreme product-market fit. Our founders’ “imagine ifs” have turned into companies like Notion, Roblox, Uber, and Square.

Chief of Staff to Bill Trenchard

We’re looking for an exceptionally sharp, relentless, and detail-obsessed Chief of Staff to serve as the trusted right hand to Partner Bill Trenchard. If you thrive in high-performance environments, love bringing structure to chaos, and are energized by keeping one of the most active investors in the business tightly organized and operating at full speed, this could be the perfect role for you.

This role is based in our San Francisco office from Tuesday to Thursday and requires a fierce work ethic, adaptability, and a “do whatever it takes” mentality—including evenings and weekends when needed.

About the Role

This is a high-velocity, high-responsibility role for someone who thrives on clarity, precision, and being in the middle of the action. Your job is to keep Bill focused, prepared, and unblocked—surfacing what matters most and owning the coordination that allows him to spend his time where it matters most.

You’ll be the connective tissue between Bill and the people around him, tracking key relationships, prioritizing urgent inputs, and ensuring follow-through on the things that drive real impact. You’ll need to move fast, communicate crisply, and stay relentlessly organized in an environment where stakes are high and pace is intense.

This isn’t a strategy job on the sidelines—it’s a hands-on execution role for someone who is hungry to learn from the best in tech and eager to earn a front-row seat to how exceptional companies are built.

Your Responsibilities Will Include:

• Serving as a key point of contact — You’ll be a first point of contact to support founders, investors, referrers, and other high-value relationships on Bill’s behalf.

• Relationship tracking and context management — You’ll ensure every founder, referrer, and investor who interacts with Bill is met with continuity, attention, and relevant follow-up. You’ll keep Salesforce and other systems up to date, and know exactly who he needs to get back to—and when.

• Preparing Bill for every interaction — You’ll prep Bill with key context ahead of every meeting, and ensure the right people are looped in on the back end. You’ll assemble briefing docs, track key threads, and proactively surface what he needs to know—and what needs his attention.

• Managing internal communication, prioritization, and coordination — You’ll wrangle communication between Bill and the teams supporting him (investment team, founder success, chiefs of staff, engineering, EA, etc.), working behind the scenes to ensure seamless execution and forward momentum.

• Supporting investment diligence & research — occasionally joining founder pitches, conducting market research, and drafting detailed snapshots to help inform investment decisions when needed.

This Role Is Not:

• A stepping stone into an investment role—it’s an opportunity to learn the ins-and-outs of venture from a top tier partner. You’ll be behind the scenes, enabling Bill and the team rather than sourcing deals or leading investments.

• All strategy, no execution—While you’ll shape high-impact processes, a major part of the job is handling unglamorous work that makes everything run smoothly.

• A 9-to-5 job—this role demands flexibility, responsiveness, and a willingness to put in time when needed, including nights and weekends.

You Might Be a Great Fit If:

• You’re extremely fast and intellectually sharp. You can read a room, read between the lines, and connect the dots quickly. You’re insatiably curious, ask insightful questions, and are lightning-fast in your thinking and work.

• You’re a phenomenal communicator. Whether written or verbal, your communication is always clear, succinct, thoughtful, and effective. You can write sharp emails, distill complex conversations, and prep a partner for a board call without needing much direction.

• You thrive in the background, making everything and everyone more effective. You take pride in being the force behind a well-oiled machine. You know the right questions to ask as well as when to listen and learn.

• You’re relentlessly organized, detail-oriented, and operate with precision and urgency in fast-paced environments. Chaos motivates you to bring order, inefficiencies don’t go unnoticed, and you take pride in moving fast.

• You can manage up and anticipate needs. You don’t wait to be told what to do—you proactively figure out what needs to be done. You have the polish and presence to regularly interact with seasoned CEOs, founders and entrepreneurs.

• You’re fascinated by technology and how today’s entrepreneurs are shaping the future. You don’t need deep knowledge of venture capital or tech, but you should be excited about the field and eager to learn quickly. Most importantly, you are a fast learner and laser-focused on execution with the drive to get things done.

• You have at least 3 years of experience in fast-moving, high-expectation environments and have a proven track record of keeping complex systems and priorities in order, and being the person others rely on to catch every last detail.

At First Round, we pride ourselves on being the most responsive, detail-oriented, and founder-obsessed firm at the earliest stages of company building. Bill is a central force behind that promise. This role is your opportunity to help him deliver at the highest level—by being the engine that keeps his attention sharp, his relationships prioritized, and his systems tight.

If you want to play a mission-critical role behind the scenes of one of the most active investors in venture, and you’re excited to apply your operational excellence, precision, and obsession with detail to help shape the way we invest in and support our founders—we’d love to hear from you.

Our Values

At First Round, we value resourcefulness, team-play, excellence and hustle. To give you a sense of what our team is all about, check out our values that guide our work:

• Try harder for founders. They’re our customers — LPs are our shareholders. We go to the ends of the earth for our founders. You might think our role as venture capitalists is to simply maximize returns. But at First Round, we believe when we put founders first, everything will follow — epic returns included. We fill in the gaps on a founder's team before they even have one and get to work on the unglamorous tasks that actually move companies forward. We'll know we've done our job when they're left feeling startled that an investor would go to these lengths for them.

• Take the wheel. Welcome to First Round. Everything is now your responsibility. Cartographers, not navigators, are the ones who tend to do well here. There are no career ladders to climb or boxes to check at First Round. If you find ways to do more for the business and our customers, your role will naturally expand alongside it. First Round is a haven for people who see themselves as architects of their reality, not casualties of circumstance. We know we have agency over our agency, and we make the conscious choice to exercise it every day.

• Treat the little things like big things. “Magic is just someone spending more time on something than anyone else might reasonably expect.” We’re all about the carefully crafted, the nitty-gritty, and the bespoke. Whether it’s hand cutting each nameplate, or debating the optimal shape of the dinner table, no detail is too small to sweat. This is decidedly not a "LGTM" culture. It is a culture where the little things are the big things.

• Give your unvarnished opinions and unwavering support. We strive to be kind, not nice. Being nice and being kind are not one and the same. In our view, kindness means being generous, helpful, and compassionate. Nice can be used as a convenient shortcut; kindness cultivates long-term excellence. One of the most (counterintuitively) compassionate things you can do is to offer your unvarnished opinion — along with your unwavering support. That willingness to risk a fleeting moment of discomfort in exchange for someone else’s growth is long-term kindness. So while we strive to be a founder’s coach in the corner, part of that responsibility requires being the kick in the ass when they need it most. We try to be as honest as possible in every encounter, whether that’s bluntly telling a founder how they can step up their game, or delivering radical candor in our feedback for teammates.

• Invent and wander. “Action produces information." We’re fans of starting small, shipping fast, and obsessively improving. The idea for the First Round Review wasn’t the product of a six-month strategy session — we wrote up a few blog posts and just shipped them. That’s because reality has a surprising amount of detail and edges that are difficult to anticipate. Each step — even the wrong one — reveals new information that improves your next move. We prefer to make the gap between having an idea and knowing if it works as small as possible.