Chief of Staff, New Verticals

About Atticus At any given time, 16 million Americans are experiencing a crisis that requires urgent help from our legal system or government. The right assistance could transform their lives. But today, most never get it. Atticus makes it easy for any sick or injured person in crisis to get the life-changing aid they deserve. In the last six years, we’ve become the leading platform connecting people with disabilities to government benefits. We also help victims of accidents, misconduct, and violence get compensation from insurance. So far, we’ve helped hundreds of thousands of people access over $10B in life-changing aid —and earned over 19,000+ five-star reviews. And we’re just getting started. We've raised more than $100 million from top VC firms like Fika, Forerunner, GV (Google Ventures), and True Ventures, with ambitions to create a category defining business assisting needy Americans. (We closed our Series C round in April 2025, so we're well-funded for the foreseeable future.) In 2025, our team grew from 151 to 210, and we will grow again in 2026. The Job As Chief of Staff, New Verticals, you'll be at the center of one of Atticus's most important strategic bets: proving out and scaling new business lines, starting with Injury. Reporting to our General Manager ( Peter Bailinson ) and partnering directly with our CEO ( Sam Byker ) and functional leaders across the company, you'll own one of our highest-priority initiatives, end-to-end. This isn't a narrowly-scoped role: you'll be taking on tough problems that come with building something new inside a scaling company—with real P&L ownership, the authority to shape strategy and operations from day one, and daily visibility at the leadership level. It demands strong judgment, comfort with ambiguity, and an instinct for what it takes to build a business. No two weeks will look the same. On a given week, you might: Design and run a test-and-learn pipeline to crack client acquisition for Injury. This could mean standing up scrappy paid channels, brokering partnerships with adjacent businesses, or piloting outreach approaches we've never tried before—then analyzing what's working and making the call on where to double down. Vibe code a new web intake flow for Injury clients from scratch. Figure out exactly what information we need to qualify and onboard a prospective client, then build and iterate a flow that collects it—while making a compelling case at every step for why Atticus is the right partner for someone navigating one of life’s hardest moments. Scope and sequence the verticals that come after Injury. Build a framework for evaluating where we’re best positioned to win, gather the data needed to stress-test each hypothesis, and own the prioritized roadmap. The role is a rare opportunity to join a fast-growing Series C startup and own a core company priority from day one. It's designed to be a path to staying here and growing as an executive—such as stepping into the GM role for a vertical you help build—or even starting your own company down the road. Qualifications Required: You’ve demonstrated insightful, decisive judgment when it comes to developing strategies, and you have a track record of making tough, smart tough calls among competing priorities. You’ve led teams of high-performing individual contributors (bonus points if they were cross-functional). You’ve steered projects where you mapped complex systems, gathered and analyzed data, made recommendations, and helped design and implement solutions. You’re a kind and thoughtful colleague who knows how to shape a great team culture, persuasively advocate for your ideas, and get buy-in from others. You have a demonstrated commitment to doing good and helping people. Bonus / Nice-to-Have: You have experience with marketplace businesses or complex consumer services (insurance, fintech, medical, real estate, etc.). You’ve done consumer-focused research or discovery work, or something else that makes you comfortable interviewing and empathizing with people from all walks of life. We are strongly committed to building a diverse team. If you’re from a background that’s underrepresented in tech, we’d love to meet you. Salary and Benefits This is a rare opportunity to join a startup that has strong traction (substantial funding, well-respected backers, tremendous growth, and many happy customers) but is still small enough that you can have a huge impact and play a role in shaping our culture. We’re a certified B Corporation tackling a critical social problem. Our mission to help people in need drives everything we do, and your work here will touch many lives. We offer competitive pay — including equity — and generous benefits: Medical and dental insurance with 100% of employees and their families premiums covered 15 vacation days & ~20 paid holidays each year (including two weeks at the end-of-year) Free membership to OneMedical $600/year internet stipend $1,000 reimbursable stipend for education and training outside of work Up to $1,200/year student loan repayment assistance 401(k) and optional HSA/FSA Humble, thoughtful, smart, fun colleagues We anticipate the base salary band for this role will be between $160,000 and $180,000 in addition to equity and benefits. The salary at offer will be determined by a number of factors such as candidate’s experience, knowledge, skills and abilities, as well as internal equity among our team. Location This job is fully remote and we’re committed to empowering everyone with flexibility. Work remotely, and travel to LA (on the company dime) as needed to be with your colleagues – usually quarterly, plus offsites. We care a lot about building a great culture and we think some interactions need to happen in person, so we put a lot of thought into retreats, offsites, and other ways to gather.