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About the Role

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.

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.

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.

Skills

Strategy
Operations
Executive Office
Consulting
Banking
Finance
Product Operations
Technical Program Leadership
Written Communication
Verbal Communication
Business Fluency
Financial Fluency
Technical Fluency
AI Validation
Cross-functional Initiative Driving
Judgment
Discretion
Systems Thinking
High Velocity Operations

Location

US & Canada (Remote)
Austin
Las Vegas
Los Angeles
Toronto

Work Type

Remote
Hybrid

Experience Level

7+ years

Benefits

Paid time off policies
401(k) match (US)
Medical/dental/vision (US)
Variety of supplemental policies (US)
Employee discounts across our portfolio of brands (US)
RRSP match (Canada)
Medical, dental, and vision coverage (Canada)
Variety of supplemental benefit options (Canada)

About the Company

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.

Equal Opportunity

CSC Generation is an equal opportunity employer. We do not discriminate on the basis of race, color, religion, sex, sexual orientation, gender identity, national origin, age, disability, veteran status, or any other characteristic protected by law.
The CSC Generation family of brands is committed to providing reasonable accommodations for qualified individuals with disabilities in our job application procedures. If you need assistance or accommodation due to a disability, please contact hrbenefits@cscshared.com.