Chief of Staff to the CEO & CTO

CSC Generation•Los Angeles, CA

1d•Remote

About The Position

CSC Generation is seeking a Chief of Staff to enhance the combined effectiveness of the CEO and CTO. This role is crucial for translating high-level discussions into concrete decisions, assigning ownership, and ensuring task completion. The Chief of Staff will act as the vital link between company strategy, technology strategy, and daily operations. This position is not merely an administrative or purely strategic role; it requires a deep understanding of the subject matter, the ability to critically assess reasoning, identify unresolved issues, and personally drive ambiguous projects to a clear outcome with a designated owner. Success within the first 6-12 months will be measured by the establishment of a robust decision-tracking system, the production of measurable outputs from executive meetings, a consistent standard of analytical rigor, and accelerated progress on priority initiatives with reduced need for re-evaluation.

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.

Nice To Haves

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

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. 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.
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.