Chief of Staff, Office of the President

About the Role

This is a rare opportunity to partner directly with Replit’s President, Michele Catasta. As Replit leads in making useful intelligence accessible to all, you will serve as the company President's primary operational and strategic force multiplier across these critical organizations.

Your mandate is to own the most complex cross-functional challenges, unblock technical and operational bottlenecks, and ensure that the core product, engineering, and organizational engines operate with speed, coherence, and precision.

This is a high-leverage individual contributor (IC) role, not a traditional management track or team-building post. You will scale your personal leverage through AI workflows, agentic automation, and rigorous analytical judgment, influence, not headcount. You are the operator Michele turns to when an issue spans multiple disciplines such as technical architecture, product execution, support feedback loops, or organizational design and demands a single, decisive owner.

What You’ll Do

• Act as Trusted Advisor & Operational Stand-in: Serve as a direct thought partner and proxy for Michele. Elevate core operational insights, synthesize briefings for high-stakes technical and organizational decisions, and step in as a representative when needed.
• Proactively Clear Cross-Functional Friction: Anticipate blind spots and resolve organizational bottlenecks before they escalate. Bridge natural seams between Engineering, Product, Support, AI teams to ensure high-cadence execution.
• Directly Responsible Individual (DRI) for Complex Initiatives: Spearhead high-priority projects that lack a neat functional home such as evolving product unit economics, developer tooling infrastructure shifts, pricing models, or technical re-architectures.
• Scale Impact via AI & Automation: Actively build and deploy AI agents, automation pipelines, and modern operational workflows to multiply your personal bandwidth across status synthesis, metrics tracking, scenario modeling, and operational monitoring.

What This Role Is Not

• Not a Routine Data / BI Role: You will not be building routine dashboards, running routine SQL queries, or handling standard quarterly analytics. Those belong to Data, RevOps, and Strategic Finance.
• Not Bureaucracy or Process for Process’s Sake: We prioritize momentum, rapid iteration, and decisiveness over heavy governance frameworks or dense slide decks.

What We Look for

• 7+ Years in High-Growth Tech: Proven track record in strategy, operations, product operations, or technical chief of staff roles, with extensive time spent working shoulder-to-shoulder with Engineering and Product leadership.
• Cross-Domain Credibility: Strong technical fluency to earn the respect of Staff/Principal Engineers and AI researchers, paired with the operational empathy to partner effectively with Support and People teams.
• Exceptional Execution in Ambiguity: The ability to take ill-defined, sprawling problems, define clean problem boundaries, and drive them to resolution without formal line authority.
• Strong Quantitative & Analytical Toolkit: Deep comfort evaluating unit economics, interrogating technical systems data, building scenario models, and separating actionable signal from noise.
• Executive-Ready Communication: Direct, concise communicator who can deliver unambiguous trade-offs and recommendations to senior leadership with clarity and brevity.
• Hands-on AI & Agent Automation: Active, practical experience leveraging LLM workflows, coding agents, and automation frameworks to amplify daily productivity and analytical depth.
• Presence & Proximity: Continual availability is essential. Ability to work in-person (at least) three days a week (Monday, Wednesday, Friday) in Foster City, CA, collaborating closely on-site with leadership.
• Scale Experience: Experience navigating rapid organizational scaling while maintaining high cultural and engineering standards.

Nice-to-haves

• Deep Developer Tooling Background: Prior experience in developer platforms, cloud infrastructure, AI coding assistants, or developer-focused software ecosystems.

How We’ll Know It’s Working

• Decision Velocity Across Functions Increases: Product, engineering, and support initiatives move from scoping to execution faster, with clear alignment and measurable business impact.
• Net-Negative Friction: Teams actively seek your partnership because your involvement removes ambiguity, sharpens priorities, and unblocks progress rather than introducing overhead.
• Integrated Health Sightlines: Replit's President has continuous, high-signal visibility into the operating health, technical execution, and organizational sentiment across all reporting groups.

Full-Time Employee Benefits Include

• Competitive Salary & Equity
• 401(k) Program with a 4% match (US Only)
• Health, Dental, Vision and Life Insurance
• Short Term and Long Term Disability
• Paid Parental, Medical, Caregiver Leave
• Flexible Time Off (FTO) + Holidays

Commuter Benefits (In-Office & US Only)

• Monthly Wellness Stipend
• Autonomous Work Environment
• In Office Set-Up Reimbursement (In-Office Only)
• Quarterly Team Gatherings
• In Office Amenities (In-Office Only)
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Interviewing + Culture at Replit

• Operating Principles

• To achieve our mission of making programming more accessible around the world, we need our team to be representative of the world.
• We welcome your unique perspective and experiences in shaping this product.
• We encourage people from all kinds of backgrounds to apply, including and especially candidates from underrepresented and non-traditional backgrounds.