Remote Chief of Staff for CEO & CTO | AI-Driven Ops

CSC Generation; Las Vegas (NV); Hybrid; USD 140,000 - 230,000; Full time

Job summary

CSC Generation is seeking a Chief of Staff to amplify the CEO and CTO partnership, translating rapid Slack threads and meetings into durable decisions with clear ownership and measurable outcomes, bridging strategy, technology, and day-to-day execution. You’ll own high-velocity initiatives, drive executive cadence, and ensure risk, finance, data, and product align.

This role demands independent validation of analyses, rigorous thinking, and the ability to push back with evidence to senior

Qualifications

• 7+ years in strategy and operations, a founder's/executive office, consulting, banking, finance, product operations, or technical program leadership.
• Exceptional written and verbal communication — you can compress messy context into a precise decision memo without losing nuance.
• Strong business and financial fluency (P&L, unit economics, business cases, experimental measurement).
• Enough technical fluency to work credibly with engineering, data, AI, and security leaders, and to spot an incomplete answer.
• Demonstrated ability to independently validate analyses and AI-assisted work.
• Track record of driving ambiguous, cross-functional initiatives from unclear problem to measurable result.
• Excellent judgment on what needs executive attention, what to delegate, and what to document.
• High discretion, low ego, and the confidence to give direct, evidence-backed pushback to senior leaders.
• Strong systems thinking — you build mechanisms that survive after you hand off the work.
• Comfort operating at high velocity across time zones, with periodic travel for executive sessions.

Responsibilities

• Capture material decisions and convert them into a durable decision log and governance register.
• Identify contradictory or stale decisions and force resolution before teams execute.
• Broadcast concise decision summaries to the right operators while protecting confidentiality.
• Run the operating cadence for the CEO–CTO partnership: agendas, pre-reads, decision prompts, action registers, and follow-through.
• Maintain a single view of top-priority initiatives with named DRIs, milestones, dependencies, and risks.
• Ensure commitments survive the meeting — confirm owners and deadlines, track completion, escalated misses.
• Preflight executive analyses: verify sources, definitions, calculations, and assumptions.
• Package recommendations in decision-ready form with what, why, what could disprove it, confidence, next action.
• Partner with Finance, Data, Product, Engineering, and brand teams to turn ambiguous questions into testable hypotheses.
• Use AI aggressively to accelerate research and execution, while independently validating AI-generated claims, code, and calculations.

Skills

Strategic planning

Operations leadership

Executive communication

Cross-functional collaboration

Risk management

AI/tech fluency

Stakeholder management

Job description

CSC Generation is seeking a Chief of Staff to amplify the CEO and CTO partnership, translating rapid Slack threads and meetings into durable decisions with clear ownership and measurable outcomes, bridging strategy, technology, and day-to-day execution. You’ll own high-velocity initiatives, drive executive cadence, and ensure risk, finance, data, and product align.

This role demands independent validation of analyses, rigorous thinking, and the ability to push back with evidence to senior