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 role

• Drive large-scale organizational transformation, translating the CEO's strategic priorities into structured programs with clear owners, milestones, and outcomes
• Lead 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 scale
• Run cross-functional growth initiatives across product, design, engineering, and marketing, keeping senior stakeholders aligned and initiatives on track
• Bring operational and execution rigor to a fast-moving environment: build the operating cadence, decision frameworks, and reporting that keep the org accountable
• Prepare the CEO for board meetings, leadership reviews, and key external moments; own follow-through on the decisions that come out of them
• Act as a horizontal influence across the executive team, building trust, brokering alignment, and unblocking work without needing to be told how
• Design how the organization works: operating model, capability, and talent systems to support scaled growth
• Drive change management across the organization, influencing teams and leaders who don't report directly to this role

About you

Minimum Qualifications

• Demonstrated experience driving transformation at scale within a large, complex tech organization
• Genuine, 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 functions
• Demonstrated operational rigor, with the ability to bring structure to chaos and stand-up process where none exists
• Analytical and data-driven, with the judgment to operate autonomously and the accountability to own outcomes
• Demonstrated ability to communicate effectively and earn influence with senior leaders across an organization
• Real commercial depth and business acumen — understands P&L dynamics and competitive market positioning
• Proven ability to drive change through an organization without direct authority over those teams
• Track 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 constructively

Preferred Qualifications

• Background 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 executive
• Comfort operating in both structured, at-scale environments and faster-moving, high-ambiguity ones

We'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 well
• Strategy & Business Acumen: Real commercial depth with a strong understanding of P&L and competitive market dynamics
• Business Rhythm: Has owned an operating cadence across a company, establishing the cadence and decision-making rhythm that drives accountability
• AI-Native Transformation: Has gotten AI adopted in an organization — not just worked adjacent to it
• Organization 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 them
• Influence: Gets outcomes without authority

What you’ll get

Our 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 us

Redfin 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 [email protected].

The 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.