Chief of Staff - Remote

Overview

Be the connective tissue that supercharges Ribbon’s growth. As our first Chief of Staff you’ll operate as an extension of the founders (report directly to the CEO) by prioritizing what matters most, driving cross-functional experiments (from customer success pilots to rev-ops overhauls), and turning ambiguous problems into shipped solutions. If you love context-switching, data-driven decision-making, and getting 0-to-1 projects over the line, this is your launchpad.

In Short

• Act as the founders’ force-multiplier: Own agenda setting, meeting prep, and follow-through so strategy turns into shipped work.
• Run high-leverage projects: Spin up and scale initiatives across customer success, revenue operations, product launches, conferences - you name it.
• Build and test experiments: Design short sprint experiments (i.e. self-serve onboarding flow, SDR playbook refresh) and hand off what works to functional owners.
• Ship the Bias Report: Lead research and data analysis to publish Ribbon’s annual AI-bias study, positioning us as the ethical standard-bearer in HR tech.
• Drive operational rigor: Stand up OKRs, dashboards, and post-mortems that keep everyone rowing in the same direction.
• Clear blockers, fast: Jump into any fire from customer escalations, rev-ops bottlenecks, hiring pipeline hiccups, and put it out.
• Amplify internal comms: Craft crisp updates and founder-level decks that translate strategy into stories the whole company rallies behind.

Requirements

• Has 3-5+ years in high-growth B2B SaaS, consulting, VC, or ops—with a record of owning 0-to-1 projects.
• Ambitious, exceptionally sharp, and adaptable: MBA not required, but boundless intellectual curiosity is.
• Mixes strategy with sweat: Comfortable shifting from board-level slides to rolling up sleeves in HubSpot or SQL.
• Commands data: Can spin up dashboards, model ROI, and separate signal from noise.
• Communicates like a founder: Clear, concise, persuasive—whether writing a two-page memo or presenting to an enterprise prospect.
• Thrives in ambiguity: Bias for action, no ego, learns fast, and loves rapid iteration.

Benefits

• Competitive salary + meaningful equity. We want you thinking like an owner because you are one.
• Cutting-edge tech. Build with the latest AI tooling, not yesterday’s stack.
• Health & wellness stipend. Your mind and body are part of the product.
• Annual international offsite. Each year, we take our team on an exciting journey to a different international destination. It’s more than just travel, it’s an investment in alignment and collaboration.
• Regular team lunches & meetups in Toronto. Remote first doesn’t mean remote only.