CSC Generation - Chief of Staff to the CEO & CTO
Requirements
• 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&Ls, 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
• Executive Decision System • Capture material decisions and convert them into a durable decision log (decision, rationale, owner, effective date, revisit conditions) and a policy/governance register. • Identify contradictory or stale decisions and force resolution before teams execute against different interpretations. • Broadcast concise decision summaries to the right operators while protecting confidentiality. • Executive Cadence & Priority Governance • Run the operating cadence for the CEO–CTO partnership: agendas, pre-reads, decision prompts, action registers, and follow-through. Improve or kill meetings without a clear decision, problem, or review purpose. • 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, escalate misses. • Metrics, Economics & Experiment Rigor • Preflight executive analyses: verify sources, definitions, calculations, and assumptions before they reach the CEO or CTO. • Package recommendations in decision-ready form — what we believe, why, what could disprove it, confidence level, 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 before they inform decisions. • Strategic Initiatives & Cross-Functional Execution • Own a small portfolio of top-priority initiatives end-to-end — from problem definition through implementation and handoff. • Step into ownerless but important work, build enough structure to execute, and transition it once stable. • Coordinate dependencies across technology, data, finance, growth, and operations; remove blockers and escalate tradeoffs without becoming a permanent substitute for functional ownership. • Operational Risk & Control • Run a risk-intake funnel for high-impact FinOps, security, data-governance, and vendor issues, with severity, owner, and deadline. • Convert spend anomalies, system limits, and recurring alerts into tracked remediation. • Surface pressure toward undocumented or risky workarounds so the accountable leader makes the tradeoff explicitly. • Give the CEO and CTO a concise view of what's off track, what changed, who owns it, and what decision (if any) is needed.
Benefits
• The people who do best here are builders. They take ownership, move fast, and want to see the direct impact of their work. • Executive Access: Work directly with the CEO and CTO on the decisions and operating systems that shape CSC at the portfolio level. • AI-Native Mandate: Help define how an AI-native organization makes decisions, validates work, governs risk, and scales execution across 13 brands. • Portfolio-Level Ownership: Shape strategy and operating rhythm across technology, economics, data, and multiple consumer businesses — with a trajectory into larger operating, strategy, product, transformation, or portfolio leadership roles. • Competitive Benefits (US): Paid time off policies, 401(k) match, medical/dental/vision and a variety of supplemental policies, and employee discounts across our portfolio of brands. • Competitive Benefits (Canada): Paid time off policies, RRSP match, medical, dental, and vision coverage, a variety of supplemental benefit options, and employee discounts across our portfolio of brands.
Apply in one click
Upload My Resume
Drop here or click to browse · Tap to choose · PDF, DOCX, DOC, RTF, TXT