About Keyway

Keyway is building the AI infrastructure powering the future of real estate. Our multi-agent platform automates high-impact workflows — from comp analysis and underwriting to document abstraction and investment scoring. We’re trusted by leading investors like Starwood Capital and Two Sigma and backed by top venture firms.

We are looking for a Chief of Staff to work directly with our CEO and leadership team to accelerate company-wide execution. This is a high-impact, high-visibility role ideal for a strategic thinker who thrives in fast-paced, high-growth environments and wants a front-row seat in company building.

What You'll Do:

• Act as a strategic thought partner to the CEO on key decisions and initiatives
• Own the CEO’s operating cadence — from leadership meetings and investor updates to board prep and strategic planning
• Drive special projects across product, ops, fundraising, hiring, or go-to-market as needed
• Serve as a connective tissue across functions, ensuring alignment and clear communication between product, growth, and engineering
• Help prioritize and track OKRs across the company
• Represent the CEO in internal and external meetings when needed
• Conduct analysis, research, and prep materials for fundraising, BD, and investor conversations

About You:

• 4–8 years of experience in top-tier strategy roles — e.g., founder, VC/PE, consulting, chief of staff, product, or BizOps.
• Excellent project management and communication skills
• Comfort in ambiguity and ability to thrive in a startup environment
• Strategic thinker with a bias for action
• Deep interest in technology, AI, and the real estate sector
• Based in New York

Personal Qualifications That We Value At Keyway:

• Entrepreneurial: comfortable talking to stakeholders to understand business needs, running small tests to validate assumptions, and refining requirements based on results
• Results orientation with a high motor and an incredible attention to detail; able to drive projects from planning to completion with limited oversight
• Superior analytical skills and attention to detail with a data-driven mentality
• A low ego and can-do attitude; willingness to admit mistakes and work to remedy them
• Flexibility to prioritize deliverables and re-prioritize them at a moment’s notice

At Keyway, we celebrate diversity and recognize the value it brings to our customers and employees. We are proud to be an equal opportunity workplace.