Chief of Staff
Be the connective tissue that accelerates Ribbon’s momentum from day one**.** As our first Chief of Staff, you’ll operate as a true extension of the founders (reporting directly to the CEO), stepping into the highest-leverage problems across the business and moving them forward fast. This role is for a high-energy, get-it-done A-player with strong financial background who thrives on context-switching, ambiguity, and making an immediate, visible impact.
If you love owning messy problems, building clarity from chaos, and turning strategy into action, this is your launchpad.
About Ribbon
Ribbon is on a mission to help every employer find the right people and hire 10× faster. Our always-on voice AI interviewers screen candidates in minutes, surface top talent automatically, and unlock speed and signal that traditional recruiting can't match and freeing recruiters to focus on what actually matters.
We work with high-volume employers, staffing firms, and enterprise teams from SMBs to Fortune 500 brands by helping them slash time-to-hire, reduce recruiter workload, and dramatically improve candidate experience, all without adding headcount.
Backed by world-class investors and already trusted by recognizable brands, Ribbon is entering its next phase of growth. Building a world-class sales engine is now the defining lever to scale a new category in hiring.
How you’ll make an impact
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.
We are looking for someone who
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.
Why Ribbon
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.
Ready to Standout? How to Apply:
We’ve ditched the cover letter and initial screening. Experience Ribbon’s product by starting your AI interview now - 24/7, no recruiter bottlenecks.
Apply in Seconds: Click here to start your AI Interview - here
Showcase Your True Potential: Go beyond your resume and let your skills shine
Stay Tuned: If you’re a match, our team will reach out fast for next steps.
We can’t wait to see how you’ll write Ribbon into every hiring story.