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Chief of Staff to the CEO & CTO

CSC Generation· Operations
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Hybrid (Austin, TX; Las Vegas, NV; Los Angeles, CA; Toronto, Ontario)Full-timePosted 2mo ago

About the role

Chief of Staff to increase the combined leverage of the CEO and CTO, turning high-velocity discussion into durable decisions, ownership, and execution across strategy, technology, and day-to-day operations.

Responsibilities

  • 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
  • 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, escalate misses
  • 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
  • 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
  • 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

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 — ability to 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

Skills

Required:Strategic decision-makingExecutive communicationCross-functional program managementFinancial fluencyAI literacy and validation

Benefits

  • 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
Last updated Oct 21, 2026. Interested? Apply on the company site.
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About CSC Generation

AI Native Retail Future: Commerce AGI

CSC Generation is the AI-native retail holding company. We modernize iconic brands with data, automation and our Genesis platform to build the future of Commerce AGI.

retailautomationAIdataplatformsmergers and acquisitions
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