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GigaGigaSan Francisco, CA

Chief Of Staff

The Chief of Staff will be the CEO's trusted operator and thought partner, responsible for strategic and operational weight, cross-functional execution, and high-stakes projects. This role involves building and leading executive office operations, managing external brand, and driving planning cycles.

200k – 250k
On-site3+ YOEExecutive Leadership

About the role

Why this role exists

The Chief of Staff is the CEO’s most trusted operator and thought partner. You help absorb the strategic and operational weight that currently sits on one person: board prep, fundraising, planning rhythms, cross-functional execution, and the high-stakes projects that determine whether the next 12 months go fast or slow. You’re also the organizational connective tissue — the information funnel, filter, and facilitator between the CEO and every internal and external stakeholder that matters.

You’re not a coordinator. You’re a force multiplier. You make the CEO’s time worth 3x, give the leadership team clarity and accountability, and keep the company’s long-term vision from getting eaten by short-term noise.

This is a high-intensity seat. We move fast, give direct feedback without ego, and value those who can take ownership over outcomes. If you want a title, this is the wrong place. If you want to be in the room where the company gets built, keep reading.

What you’ll own

Executive Office & CEO Leverage

  • Build and lead the daily operations of the executive office — the processes, rhythms, and infrastructure that let the CEO operate with the highest leverage
  • Act as an extension of the CEO with internal and external stakeholders: assess all incoming inquiries, determine priority and proper course of action, and route or handle accordingly
  • Serve as the primary point of contact for the CEO’s direct reports; work in close partnership with the EA to ensure the CEO’s calendar is tightly aligned with company priorities
  • Stand in for the CEO in selected meetings, challenge ideas, offer perspective, and drive follow-through on action items
  • Manage the CEO’s external brand and reputation, including how they show up with investors, customers, and the broader ecosystem

Operating Rhythm & Planning

  • Build and run the cadence for leadership meetings, board meetings, and leadership offsites — including structuring and helping deliver company-wide communications
  • Drive quarterly planning cycles, OKRs, leadership reviews, and major business updates
  • Own the company operating dashboard: define the metrics, instrument them, track them weekly, and flag what’s slipping before anyone has to ask. Nobody should know the state of the business better than you
  • Design meetings so they’re decisive, not just informative — sharper agendas, cleaner decisions, ruthless follow-through

Cross-Functional Execution

  • Lead strategic initiatives end-to-end that span Eng, GTM, and Ops — especially work that doesn’t neatly fit within the org chart or falls between departments. From “here’s a messy problem” to “it’s done, here’s the result”
  • Proactively track high-priority initiatives, surface blockers and dependencies early, and follow up with owners when goals aren’t being met — with actionable recommendations, not just status updates
  • Promote team integration, cross-functional communication, and collaboration across the organization

Board, Investors & Stakeholder Management

  • Own board cadence: deck production, narrative, data room, and all prep that makes every board interaction count
  • Support fundraising — modeling, materials, diligence coordination
  • Build and maintain a process to track and nurture key relationships across investors, customers, and strategic partners
  • Synthesize business performance, risks, and open decisions into crisp communications for external audiences

Strategic Advisory

  • Serve as a genuine thought partner to the CEO: challenge assumptions, offer a different perspective, and help think through high-impact decisions with analysis, options, and clear recommendations
  • Live in the future — maintain focus on long-term planning and strategic priorities even as the day-to-day demands attention

Who you are

  • 3–7 years of demonstrated slope in BizOps, strategy, or operator roles at high-velocity companies — frontier AI labs, top-tier startups, or the consulting/banking-to-operator path. We index on what you owned and the delta you created, not your résumé
  • AI-native. You’ve shipped or operated close to LLM products and understand eval and inference economics well enough to be dangerous. You don’t need it explained to you
  • Exceptional writer and thinker. Muddy writing is muddy thinking — we’ll test for it
  • Superb judgment with confidential information, competing priorities, and executive-level relationships — internally and externally
  • Proven track record leading complex, multi-stakeholder initiatives from ambiguous start to clean finish
  • High floor under pressure. You hold the line when things are on fire.
  • Low ego, high ownership — you don’t need credit, you need things to get done

What the first 90 days look like

  • Day 30: You’ve absorbed the operating cadence, mapped where the gaps are across every function, taken at least two recurring time-sinks off the CEO’s plate, and established yourself as the go-to for CEO office matters
  • Day 60: The company dashboard is live and you’re running the weekly metrics review. Board prep and at least one cross-functional initiative are yours end-to-end. People come to you, not the CEO, for status
  • Day 90: Planning cycles are tighter. Leadership meetings are more decisive. Strategic initiatives stay moving across team boundaries. The CEO has visibly more leverage — measurably more time on product, customers, and recruiting

Perks & Benefits

  • Competitive base + bonus + meaningful equity
  • Catered lunch daily
  • Dinner stipend
  • $500/month wellness & commuter benefit (gym, fitness classes, mental health)
  • 401(k) plan
  • Medical, dental, and vision coverage

Skills

AILLMsStrategic PlanningCross-Functional CollaborationStakeholder ManagementBusiness OperationsFundraisingData AnalysisCommunication
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