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. 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.

Responsibilities

Capture material decisions and convert them into a durable decision log; Identify contradictory or stale decisions and force resolution; Broadcast concise decision summaries to the right operators while protecting confidentiality; Run the operating cadence for the CEO-CTO partnership; Maintain a single view of top-priority initiatives with named DRIs; Ensure commitments survive the meeting; Preflight executive analyses; Package recommendations in decision-ready form; Partner with Finance, Data, Product, Engineering, and brand teams; Use AI aggressively to accelerate research and execution while validating AI-generated claims; Own a small portfolio of top-priority initiatives end-to-end; Step into ownerless but important work; Coordinate dependencies across technology, data, finance, growth, and operations; Run a risk-intake funnel for high-impact FinOps, security, data-governance, and vendor issues; Convert spend anomalies, system limits, and recurring alerts into tracked remediation; Surface pressure toward undocumented or risky workarounds; Give the CEO and CTO a concise view of what's off track

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; Candidates must reside in one of Austin, Las Vegas, Los Angeles, or Toronto and be comfortable with hybrid work; US-based candidates must reside in AZ, DE, FL, GA, IN, LA, MI, MS, MO, NV, NC, OK, PA, TN, TX, UT, WV, WI, or WY

Nice to have

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

Benefits

Executive Access; AI-Native Mandate; Portfolio-Level Ownership; Paid time off policies; 401(k) match; medical/dental/vision and supplemental policies; employee discounts across our portfolio of brands; RRSP match; medical, dental, and vision coverage; supplemental benefit options; employee discounts across our portfolio of brands