Chief of Staff

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.

We’re looking for an exceptionally sharp, relentless, and highly responsive 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 get excited about leveraging AI and automation to improve workflows, 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 not a typical Chief of Staff role—it’s for someone who thrives on creating order from chaos and driving operational excellence. You’ll be responsible for optimizing daily operations, managing relationships, streamlining processes, and ensuring Bill is always focused on the highest-value work.

You’ll own the systems that make Bill more effective—whether that’s logging and leveraging data in Salesforce, improving workflows with AI, or ensuring the right opportunities, people, and priorities are surfaced at the right time. You won’t just maintain processes—you’ll elevate them, automate them, and rethink them to make everything run smoother and smarter.

Responsibilities include:

• Mastering Bill’s communication & email management—responding within minutes, filtering for priority, and ensuring everything is organized and actionable.

• Serving as a key point of contact—supporting founders, investors, referrers, and other high-value relationships on Bill’s behalf.

• Driving process optimization, automation, and AI integration—leveraging tools like Zapier, Notion, Airtable, Gumloop, and LLMs to make our systems smarter.

• Tracking and maintaining key data in tools like Salesforce—not just logging information, but deeply understanding why we track it and how to use it to drive better investment decisions.

• Preparing Bill for every interaction—assembling briefing books, tracking key conversations, and proactively surfacing important insights.

• Managing partner projects, events, and special initiatives—working behind the scenes to ensure seamless execution.

• 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 obsessed with making things run faster, smoother, and smarter. If something can be automated, templatized, or improved, you’re on it.

• 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, staying highly responsive, and ensuring nothing slips through the cracks.

• You enjoy both high-level strategy and hands-on execution. You’re just as comfortable logging and analyzing Salesforce data as you are managing high-profile relationships.

• 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 an exceptional communicator. Whether it’s drafting an email, summarizing research, or flagging priorities, your written and verbal communication is always clear and effective.

• You’re fascinated by technology and how today’s entrepreneurs are shaping the future. You don’t necessarily need deep knowledge of the venture capital industry, but you should be excited about the field and eager to learn the business 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 a Chief of Staff, Business Operations, or similar role. Bonus if you’ve worked in fast-moving, high-expectation environments.

This is a rare opportunity to work at the center of a leading venture firm, optimize the way an industry leader operates, and directly impact how we invest in and support the world’s best founders. If you’re excited about using technology, automation, and operational excellence to drive efficiency at the highest levels of venture capital, we’d love to hear from you.

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. Going above and beyond for our founders is what we do. We strive to be a founder's most valuable investor. That’s why we don't pull term sheets, and we're always in for their second round. We respond to their emails in hours, not days. We build candidate pipelines, unprompted. We arrange meal deliveries when they become a new parent. Simply put, we go above and beyond to earn that right to be their first call every time there’s a bump in the road.

• Give your unvarnished opinions and unwavering support. We strive to be kind, not nice. 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.

• Treat the little things like big things. Everything can always be made better. 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.

• Make speed a habit. Whatever you’re building, remember that now is better than two weeks from now. We’re fans of starting small and iterating quickly. No matter what we’re launching, you’ll likely hear this question in a meeting: “How soon can we get something out there?”

• Invent and wander. Never stop experimenting. The best ideas are born out of experimentation. Our flagship programs have always come from our penchant for going out on a limb and approaching problems with a different perspective.

• Build wider doorways and longer tables. We're in the business of backing people and betting on their ideas — no matter where they come from. While talent is evenly distributed, opportunity is not. First Round is dedicated to building a diverse and inclusive workspace and we encourage people from underrepresented groups to apply!