Chief of Staff

THE ROLE

Given KEH’s current size — over two hundred employees across operations, technology, merchandising, and commerce functions — and ongoing anticipated rapid growth, as well as its need to level-up its operating capabilities to meet the needs of its size and ambition, the Company’s go-forward performnce depends on how well its operating system runs: the cadence of leadership meetings, the flow of decisions and information to and from the CEO, and the follow-through that turns priorities into completed work. To meet these needs, the CEO is planning to install a defined operating system — a weekly leadership rhythm with an owned scorecard, published decision rights with escalation thresholds, written decision memos, a weekly metrics review, structured visibility into the levels below the leadership team, and other elements. The Chief of Staff exists to make that system actually run, every week, without decay — and to multiply the CEO’s capacity by owning the connective work that today competes with the work only the CEO can do.

The scope is the machinery of the Office of the CEO: the operating cadence and its artifacts (agendas, scorecard, one-pagers, metrics review), the integrity of the decision-rights system (memos routed to the right decider, escalation thresholds enforced, commitments tracked to closure), the preparation that makes the CEO effective in every meeting that remains on his calendar, and the integration across major cross-functional initiatives — including implementing and integrating AI, upgraded financial management through a new ERP, ongoing improvements across the technology stack as well as in IT infrastructure, continued up-leveling of pricing capabilities, extensive increases in analytics and reporting on key metrics, more sophisticated product information management, brand and others — where workstreams must connect but no single function can deliver the whole itself. This is a role of substantial influence and zero formal authority: it succeeds through judgment, preparation, trust, and follow-through. The right leader for this role is both strategic and hands-on who will develop and execute the strategies and leverage the resources/departments at the Company to assist in such.

This is not an executive assistant role, and it is not a shadow chief operating officer. The Chief of Staff does not make the leadership team’s decisions and does not sit between the CEO and his direct reports as a gatekeeper. The role is an integrator and honest broker: it makes the organization’s information flow faster and truer, makes the CEO’s time compound, and makes the operating system impossible to quietly abandon.

WHAT YOU WILL OWN

• The operating cadence. The weekly leadership tactical meeting, monthly strategic meeting, quarterly off-site, monthly all-managers forum, and quarterly skip-level program run on schedule, with agendas, prework, and outcomes documented — and their quality is audited quarterly rather than allowed to decay.
• The information architecture. Friday one-pagers from the leadership team arrive on time in a fixed format; the weekly metrics review runs on standardized, exception-flagged input metrics; the CEO’s briefing packets make him the most prepared person in every meeting he attends.
• The decision system. The published decision-rights map is enforced in practice: decisions the CEO retains arrive as written memos with recommendations; escalations respect thresholds; send-backs are routed to the right owner; commitments made in any forum are tracked to closure.
• Cross-functional integration of CEO priorities. The handful of initiatives that span functions — including the initiatives mentioned above — stay connected: dependencies surfaced early, conflicts brokered at the working level, and only genuine gate decisions elevated.
• CEO leverage. Leveraging the executive-assistant capacity, the CEO’s calendar reflects his stated priorities — meeting defaults enforced, think blocks protected, and the reactive share of his week measurably reduced.

WHAT YOU WILL DO

• Run the mechanics of the weekly leadership meeting: own the scorecard’s integrity, build the agenda from exceptions and decisions needed, document outcomes and owners, and track every commitment to closure.
• Produce the CEO’s briefing packets — context, prior commitments, open issues, and a recommended position — for board meetings, partner meetings, and key internal sessions.
• Draft, route, and quality-control decision memos: ensure every retained decision arrives with options considered, a recommendation, reversibility classification, and a deadline.
• Enforce the escalation thresholds in the decision-rights map, and execute the send-back rule — returning misrouted decisions to their owner with guidance rather than letting them accumulate at the top.
• Stand up and run the monthly all-managers forum (the company’s ~20–35 managers) and coordinate the quarterly skip-level program, so the manager layer hears priorities first and unfiltered signal reaches the CEO.
• Operate the weekly metrics review: standardized charts on controllable input metrics — buy-side intake, grading and refurbishment throughput, pricing realization, sell-through, conversion, KEH Certified return rates — with discussion reserved for exceptions.
• Broker conflicts on cross-functional initiatives and projects at the working level, elevating only what genuinely requires the CEO or the leadership team.
• Run the quarterly meeting audit: what decision or exception does each recurring meeting surface, and what can the one-pager, the metrics review, or an owner now cover instead.
• Manage follow-through on board and D Cubed commitments, and support the CEO’s preparation for quarterly board meetings.
• Serve as honest broker: carry unfiltered ground truth to the CEO — including bad news — and carry the CEO’s intent accurately into and across the organization.
• Direct the CEO-office executive assistant capacity (calendar architecture, inbox triage, logistics) as it is established.

WHAT WE ARE LOOKING FOR

Required

• 8–12+ years of professional experience, including 3+ years leading cross-functional programs, business operations, or strategy execution in an operating company — with a track record of making complex, multi-stakeholder work actually finish.
• Direct experience building or running management operating rhythms: leadership meeting systems, KPI scorecards or weekly business reviews, and written decision or planning processes.
• Exceptional structured written communication — this role produces decision memos, briefing packets, and meeting documentation that senior leaders act on without a second draft.
• Demonstrated ability to influence senior leaders without formal authority, and the judgment to know what to elevate, what to broker, and what to leave alone.
• Analytical fluency: comfortable owning a metrics review, interrogating a dashboard, and pressure-testing the numbers behind a recommendation.
• Impeccable discretion and demonstrated trustworthiness with confidential executive, personnel, and investor matters.
• Relentless follow-through: a visible system for tracking commitments, and a reputation for nothing falling through the cracks.

Preferred

• Experience in retail, e-commerce, consumer operations, or re-commerce/circular-economy businesses.
• Exposure to a major systems transformation (ERP migration or comparable) or other transformative aspects of an operatingcompany’s operations.
• Prior chief of staff, business operations, or top-tier consulting experience serving C-level executives.
• MBA or comparable advanced training in business operations or strategy.

WHO YOU ARE

You are a low-ego force multiplier: you measure your success by whether the CEO and the leadership team perform better, and you are comfortable doing consequential work whose fingerprints are mostly invisible. You are direct, organized, and unafraid to tell the most senior person in the room an uncomfortable truth — and you handle what you know with absolute discretion. You bring urgency and structure to an environment that is professionalizing fast, and you would rather enforce a standard cheerfully a hundred times than let a system quietly decay.

KEY PERFORMANCE INDICATORS

• CEO time: reactive meeting hours measurably reduced against baseline; two 90-minute think blocks per week protected and actually held.
• Decision quality of flow: more than 80% of CEO-retained decisions arriving as written memos with a recommendation; median decision-turnaround time tracked and falling.
• Cadence adherence: weekly leadership meeting, Friday one-pagers, and weekly metrics review each running at or above 90% on-schedule with artifacts complete.
• Follow-through: commitment-closure rate from leadership forums tracked and above 90% by day 180.
• System health: quarterly meeting audit completed and acted on; manager-forum and skip-level programs running on schedule.