Chief of Staff
You operate seamlessly between strategy and action: trusted partner, gatekeeper, sounding board, and execution lead for the CEO’s most sensitive priorities. Those with a career history in digital and eCommerce, advertising and marketing operations will have stand out knowledge as they have a better than agency internal team for those functions.
You’re an AI-native and tech-savvy, using tools like Claude Code or similar daily at an intermediate–advanced level and certainly come from that type of company environment eg AI native or early adopters as this business aims to become AI first (where appropriate). This client has an AI technical team for programming your workflow requirements of the SLT and their teams, where human first SOPs are being replaced.
Your Profile- Strong D2C customer acquisition and retention, eCommerce, performance advertising and digital marketplace understandand experience of those GTM and TOMs including subscription and membership growth (web or mobile apps)
- Passion for eLearning, online training, sporting goods, health, wellness, fitness, or biohacking could be a good culture fit
- 7–12+ years supporting CEOs/Founders in fast-scaling SMBs
- Experience scaling a 100–300 person company (ideally 2+ examples each with 3+ years tenure)
- Board-level confidence: meetings, materials, investors, confidentiality
- USA/CAN-based, fully remote
- Interested in golf
Core Responsibilities
Translate CEO & Board vision into priorities, OKRs, and execution plans
Drive cross-functional initiatives and operating cadence
Prepare CEO for board, investor, and key stakeholder engagements
Provide research, analysis, and decision support
Act as communication bridge across the executive team
Lead high-impact special projects (scale, M&A, market entry)
Run executive and SLT meetings with clear follow-through
Track priorities, metrics, and accountability
Draft CEO communications (internal & external)
Coordinate board and investor materials
Resolve cross-functional blockers
Own “CEO-only” initiatives end-to-end
Surface risks early and proactively close gaps
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