Chief of Staff to the CEO & CTO

CSC Generation is the AI-native holding company re-engineering omnichannel retail. We acquire iconic brands and transform them with Genesis, our operating platform combining a Data Fabric, Automation Engine, proprietary tools, and shared services to modernize operations, elevate customer experience, and expand margins. With $1B+ in revenue across 13 brands, our portfolio includes Sur La Table, Backcountry, One Kings Lane, and others that serve as real-world innovation labs.

Reports to: Chief Executive Officer; primary executive partners are the CEO and Chief Technology Officer

Location: US & Canada (Remote), with regular travel to work in person with the CEO and CTO;
Austin, Las Vegas, Los Angeles, or Toronto preferred.
Candidates must reside in one of these locations and be comfortable with hybrid work.

We are hiring a Chief of Staff to increase the combined leverage of the CEO and CTO. As Chief of Staff to the CEO & CTO
, you will turn high-velocity discussion across Slack, meetings, and operating reviews into durable decisions, clear ownership, and completed work — building the connective system between company strategy, technology strategy, and day-to-day execution.

This is not an executive assistant, pure coordination, or strategy-only role. You will understand the substance, challenge weak reasoning, spot what hasn't been decided, and personally drive ambiguous work until it has a capable owner and a measurable outcome. Success in the first 6–12 months means decisions are captured and easy to retrieve, the executive cadence produces measurable outputs, analyses meet a consistent bar for rigor, and priority initiatives move faster with less re-litigation.

This is a lean team. You will own a lot, move fast, and make decisions with full end-to-end responsibility.

• 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, escalated 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 elevate tradeoffs without becoming a permanent substitute for functional ownership.

• Run a risk-intake funnel for high-impact Fin Ops, 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…