Chief of Staff

Redfin is scaling fast and reinventing itself as an AI-native company. The Chief of Staff to the CEO will be the force multiplier behind that transformation — turning the CEO's biggest bets into structured, cross-functional execution, and driving AI adoption across people, process, and capabilities. This is a high-impact, high-autonomy role for an operator who brings rigor to ambiguity and can influence senior leaders horizontally without formal authority. The Chief of Staff will operate as a trusted partner to the CEO and the executive team: framing decisions, leading company-wide initiatives, and making sure the organization moves with clarity, speed, and accountability.About the roleDrive large-scale organizational transformation, translating the CEO's strategic priorities into structured programs with clear owners, milestones, and outcomesLead the company's AI adoption and transformation, bringing a real technical understanding of AI to reshape how teams work, what they build, and how they operate at scaleRun cross-functional growth initiatives across product, design, engineering, and marketing, keeping senior stakeholders aligned and initiatives on trackBring operational and execution rigor to a fast-moving environment: build the operating cadence, decision frameworks, and reporting that keep the org accountablePrepare the CEO for board meetings, leadership reviews, and key external moments; own follow-through on the decisions that come out of themAct as a horizontal influence across the executive team, building trust, brokering alignment, and unblocking work without needing to be told howDesign how the organization works: operating model, capability, and talent systems to support scaled growthDrive change management across the organization, influencing teams and leaders who don't report directly to this roleAbout youMinimum Qualifications Demonstrated experience driving transformation at scale within a large, complex tech organizationGenuine, hands-on AI fluency — experience personally leading AI adoption or transformation initiatives (not just working adjacent to it)Strong track record of cross-functional program leadership across product, engineering, design, and go-to-market functionsDemonstrated operational rigor, with the ability to bring structure to chaos and stand-up process where none existsAnalytical and data-driven, with the judgment to operate autonomously and the accountability to own outcomesDemonstrated ability to communicate effectively and earn influence with senior leaders across an organizationReal commercial depth and business acumen — understands P&L dynamics and competitive market positioningProven ability to drive change through an organization without direct authority over those teamsTrack record of owning an operating cadence across a company (not just a team)Ability to serve as a trusted thought partner who can disagree well and challenge thinking constructivelyPreferred QualificationsBackground at a large-scale, high-caliber tech/AI environment in a Chief of Staff, Business Lead, or Director of Business Operations capacity Experience partnering directly with a CEO or C-suite executiveComfort operating in both structured, at-scale environments and faster-moving, high-ambiguity onesWe're looking for someone with demonstrated excellence within these core focus areas:Sounding Board: A trusted thought partner who can challenge ideas constructively and disagree wellStrategy & Business Acumen: Real commercial depth with a strong understanding of P&L and competitive market dynamicsBusiness Rhythm: Has owned an operating cadence across a company, establishing the cadence and decision-making rhythm that drives accountabilityAI-Native Transformation: Has gotten AI adopted in an organization — not just worked adjacent to itOrganization Building: Designs how the org works: operating model, capability, and talent systems (not headcount management)Change Management: Has driven change through an organization that didn't report to themInfluence: Gets outcomes without authorityWhat you’ll getOur team members fuel our strategy, innovation and growth, so we ensure the health and well-being of not just you, but your family, too! We go above and beyond to give you the support you need on an individual level and offer all sorts of ways to help you live your best life. We are proud to offer eligible team members perks and health benefits that will help you have peace of mind. Simply put: We’ve got your back. Check out our full list of Benefits and Perks.About usRedfin is a technology-driven real estate company with the country's most-visited real estate brokerage website. As part of Rocket Companies (NYSE: RKT), Redfin is creating an integrated homeownership platform from search to close to make the dream of homeownership more affordable and accessible for everyone. Redfin’s clients can see homes first with on-demand tours, easily apply for a home loan with Rocket Mortgage, and save thousands in fees while working with a top local agent. This job description is an outline of the primary responsibilities of this position and may be modified at the discretion of the company at any time.  Decisions related to employment are not based on race, color, religion, national origin, sex, physical or mental disability, sexual orientation, gender identity or expression, age, military or veteran status or any other characteristic protected by state or federal law.  The company provides reasonable accommodations to qualified individuals with disabilities in accordance with applicable state and federal laws.  Applicants requiring reasonable accommodations in completing the application and/or participating in the application process should contact a member of the Human Resources team, at View email address on us.fitly.work compensation information below is provided in compliance with all applicable job posting disclosure requirements. The compensation for this position is $162,000.00-$343,000.00. The position may also be eligible for an annual bonus, incentives, and other employment-related benefits including, but not limited to, medical, dental, and vision benefits, 401K retirement plan, and paid-time off. More information regarding these benefits and others can be found here. The information regarding compensation and other benefits included in this paragraph is the company’s current, good faith estimate at the time of posting. [Compensation and benefits are subject to modification from time to time as the Company, in its sole and exclusive discretion, deems appropriate.] The Company may determine during its future reviews of the proposed compensation and benefits provided for this position, that the compensation and benefits for such position should be reduced. In no event will the Company reduce the compensation for the position to a level below the applicable jurisdictional minimum wage rate for the position. Los Angeles County and San Francisco Candidates only: qualified applicants with arrest or conviction records will be considered for employment per the Fair Chance Ordinance and the Fair Chance Initiative for Hiring.SummaryLocation: Seattle, WAType: Full time