Chief of Staff to the CEO & CTO
On-siteToronto, Ontario, Canada or Los Angeles, California, United States
Job Summary
Capture material decisions into a durable log and policy register, then broadcast concise summaries to operators while resolving contradictory interpretations. Run the CEO–CTO operating cadence, maintaining a single view of top-priority initiatives with named DRIs and escalating missed commitments. Preflight executive analyses for rigor, package recommendations with confidence levels, and use AI aggressively while independently validating all generated claims. Own end-to-end execution of top-priority initiatives, coordinate cross-functional dependencies, and run a risk-intake funnel for FinOps, security, and vendor issues. Convert anomalies into tracked remediation and surface pressure toward risky workarounds so accountable leaders make explicit tradeoffs. Provide the leadership team with a concise view of what is off track and what decisions are 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.
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