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 accountabilityAI-Native Transformation:
Has…