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.

• 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

• 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

• 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…