Chief of Staff, Office of the President

Replit•Foster City, CA

2d•$200,000 - $300,000•Hybrid

About The Position

The Chief of Staff is a high-leverage individual contributor who partners directly with Replit President Michele Catasta as an operational and strategic force multiplier. The role owns complex cross-functional challenges, removes technical and operational bottlenecks, and helps the product, engineering, and organizational functions operate with speed and clarity. It is not a traditional management or team-building role; the person scales their impact through AI workflows, agentic automation, analytical judgment, and influence rather than headcount. The position spans issues involving technical architecture, product execution, support feedback loops, and organizational design. The Chief of Staff serves as a trusted advisor and operational stand-in for the President, resolves friction across Engineering, Product, Support, and AI teams, and leads complex initiatives without a clear functional home. The role also builds and deploys AI agents, automation pipelines, and operational workflows to increase capacity for synthesis, metrics tracking, scenario modeling, and operational monitoring. This role is based in Foster City, California, with in-person work at least three days per week (Monday, Wednesday, and Friday), collaborating closely with leadership. Success means faster cross-functional decision-making and execution, reduced friction for teams, and continuous high-signal visibility for the President into operating health, technical execution, and organizational sentiment.

Requirements

At least 7 years of experience in high-growth technology, with a track record in strategy, operations, product operations, or technical chief of staff roles.
Extensive experience working closely with Engineering and Product leadership.
Technical fluency sufficient to earn the respect of Staff and Principal Engineers and AI researchers, along with operational empathy to work effectively with Support and People teams.
Ability to define and resolve ambiguous, sprawling problems without formal line authority.
Strong quantitative and analytical skills, including evaluating unit economics, analyzing technical systems data, building scenario models, and identifying actionable signal.
Ability to communicate directly and concisely, presenting clear trade-offs and recommendations to senior leaders.
Practical experience using LLM workflows, coding agents, and automation frameworks to improve productivity and analytical depth.
Ability to work in person in Foster City, California, at least three days per week: Monday, Wednesday, and Friday.
Experience navigating rapid organizational scaling while maintaining high cultural and engineering standards.

Nice To Haves

Background in developer platforms, cloud infrastructure, AI coding assistants, or developer-focused software ecosystems.

Responsibilities

Serve as a trusted advisor, direct thought partner, and operational proxy for the President.
Surface operational insights and synthesize briefings for high-stakes technical and organizational decisions.
Represent the President when needed.
Anticipate blind spots and resolve organizational bottlenecks before they escalate.
Bridge Engineering, Product, Support, and AI teams to enable high-cadence execution.
Lead high-priority cross-functional initiatives without a clear functional owner, including work involving product unit economics, developer tooling infrastructure, pricing models, and technical re-architectures.
Build and deploy AI agents, automation pipelines, and operational workflows to increase personal capacity for status synthesis, metrics tracking, scenario modeling, and operational monitoring.
Help increase decision velocity, reduce cross-functional friction, and provide the President with high-signal visibility into organizational and technical health.