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. 

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.

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 [email protected].

For Ontario applicants, please note that this posting is for an existing vacancy.

For US-based candidates, this posting is intended for candidates that reside in the following states:
AZ, DE, FL, GA, IN, LA, MI, MS, MO, NV, NC, OK, PA, TN, TX, UT, WV, WI, and WY.