Chief of Staff

The Role

Chief of Staff to the CEO driving company-wide transformation, AI adoption, cross-functional growth initiatives, operating cadence, executive decision support, organizational design, and change management. The role requires influencing senior leaders without formal authority, translating strategy into accountable programs, preparing leadership and board materials, and serving as a trusted thought partner to the CEO and executive team.

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.