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 fast-paced, 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—triaging his inbox, surfacing what matters most, and owning the coordination that allow 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:

• Mastering Bill’s communication & email — You’ll be in Bill’s email daily, responding within minutes, escalating what matters most, and filtering out what doesn’t.

• 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. Bill spends a large portion of the day in his inbox - and you will too.

• 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 y