Hybrid Chief of Staff

at Ribbon

• Job title: Chief of Staff
• Job type: Full Time
• Experience level: Lead
• Salary: Not specified
• Degree requirement: No Education Requirement
• Tech skills: Switching
• Location requirements: Hybrid, Toronto, Canada

About the role

• Chief of Staff at Ribbon driving high-impact projects and aligning teams for strategic execution. Focusing on financial rigor and operational cadence to accelerate momentum across the organization.

Responsibilities

• Be the founders' force multiplier: Drive prioritization, prep, and follow-through so decisions don't stall, turn strategy into execution.
• Own high-impact projects end-to-end: Step into critical initiatives across finance, rev-ops, customer success, partnerships, and product - push them forward and ship.
• Bring financial rigor to decision-making: Build models, evaluate ROI, pressure-test assumptions, and help the team make fast, informed calls.
• Run rapid experiments: Design and execute short-cycle tests (pricing, onboarding, GTM motions), double down on what works, and hand off cleanly.
• Drive operational cadence: Implement dashboards, OKRs, and operating rhythms that raise the bar on accountability and clarity.
• Unblock the business: Jump into live issues including customer escalations, pipeline bottlenecks, hiring gaps and move things forward without waiting for permission.
• Own executive-level communication: Create crisp updates, board-ready decks, and internal narratives that align the team and investors.
• Lead the Bias Report: Own the research, analysis, and delivery of Ribbon’s annual AI bias report, reinforcing our leadership in ethical AI hiring.

Requirements

• Has 5+ years in high-growth B2B SaaS, consulting, investing, or ops and a track record of owning and shipping 0-to-1 projects.
• Brings strong finance experience: comfortable with models, metrics, unit economics, and translating numbers into decisions.
• Is a high-energy A-player: proactive, relentless, and wired to move things forward without being asked.
• Thrives in constant context-switching: Can juggle multiple priorities and still execute with precision.
• Mixes strategy with execution: Equally comfortable in board-level conversations and in the weeds (CRM, spreadsheets, tooling).
• Data-first thinker: Knows how to find signal, build dashboards, and cut through noise.
• Communicates like an owner: Clear, concise, persuasive both written and verbal.
• Has a bias for action and learning: Low ego, fast learner, and allergic to inertia.

Benefits

• Competitive salary + meaningful equity.
• Cutting-edge tech.
• Health & wellness stipend.
• Annual international offsite.
• Regular team lunches & meetups in Toronto.