CareerPlan

Chief of Staff

TorontoFull-time2026-10-19 → 2026-11-10
Hybrid

Core

Chief of Staff to the CEO responsible for executive alignment, OKRs, leadership operating cadence, board governance, strategic projects, and M&A coordination.

Role type

Senior IC Chief of Staff

Builds

Integrated leadership operating system, OKR framework, board packs, strategic initiatives, and M&A pipelines

Domain

B2B SaaS / Fintech / Payments / Education Technology

Required skills

Executive alignment, OKR design and tracking, leadership operating cadence, board governance, strategic project management, M&A coordination, CEO thought partnership, influence without authority, commercial and financial fluency, operating rigor

Preferred skills

Strategy consulting, investment banking, corporate development, board work, M&A diligence, education technology, public sector, bilingual English and French, MBA

Technologies

None stated

Responsibilities

Turn CEO priorities into company OKRs with clear owners and measures; run the weekly CEO staff meeting and maintain the action log; lead the quarterly OKR reset and integrated leadership calendar; assemble quarterly board packs and track board/executive actions; lead 2-3 CEO-sponsored strategic initiatives; run weekly M&A pipeline reviews and coordinate integration handoffs; draft CEO communications and act as thought partner

Seniority

Senior, hands-on IC