Chief of Staff to the CEO & CTO

Job description

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.** ### 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. ### What You'll Do #### **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. ### Required 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 — 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. ### Preferred 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 — 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. ### Why Join 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. ### Interview Process 1. **Recruiter Screen** - A 30-minute conversation with our recruiting team to align on background, role fit, operating style, and logistics. 2. **Working Session with CEO & CTO** - A session focused on judgment, executive partnership, prioritization, and your ability to create clarity from incomplete information. 3. **Practical Case** - Turn a realistic set of Slack threads, metrics, risks, and conflicting inputs into a concise decision artifact and execution plan. 4. **Cross-Functional Interviews** - Conversations with leaders who will rely on this role to create alignment and follow-through. 5. **In-Person Interview** - We'd like to meet you at our Austin office (or an alternate location coordinated with your recruiter). Details and logistics will be arranged with your recruiter. 6. **Reference Checks** - Conducted in parallel with the final stages where possible. 7. **Offer** - We move quickly for the right candidate. *Interview process is subject to change. Any updates will be communicated promptly and clearly.*