Chief of Staff
About The Position
We’re seeking a Chief of Staff to join our Executive team at FutureFit AI. This role is designed to extend the executive team’s bandwidth on executional and logistical work, with a split of roughly sixty percent dedicated to executive support and forty percent to project and operations work. The ideal candidate will aggressively wield the modern AI toolkit to enhance productivity. FutureFit AI's mission is to help more people get to better jobs faster and cheaper, focusing on those facing barriers to opportunity and addressing economic inequality through an AI-powered platform for workforce development.
Requirements
- Five-plus years supporting a senior executive, ideally a founder or CEO at a venture-backed company, as an EA or as a Chief of Staff
- A demonstrated track record of taking on project work without dropping the core role.
- Comfort with ambiguity, confidential information, and a calendar that can change by the hour.
- Fluency with the modern AI toolkit. You use it daily, you have opinions about which tools earn their keep, and you are not waiting for permission to deploy them.
- Comfort with occasional flex outside standard business hours during periods of high intensity, and in-person availability on short notice when the work calls for it.
Nice To Haves
- Experience at a high-growth Series A through C startup.
- Event production or offsite logistics chops.
- Light project management discipline; you can build a simple tracker without one being handed to you.
- Background in workforce development, AI, or B2B SaaS.
Responsibilities
- Executive time and inboxes: Calendar architecture, prioritization, and gatekeeping, with the judgment to make tradeoff calls without checking first.
- Travel and the mechanics of the week: Booking, expenses, logistics, the small frictions that compound into lost hours if left untended.
- Pre-reads and preparation: Briefing documents for recurring meetings, so the CEO walks in already knowing what matters.
- Project work for the executive team: Offsites, executive travel, senior-hire candidate experience, event logistics, the operational scaffolding around important moments.
- Operations support: Cross-functional ops support during inflection points, in partnership with Strategy & Operations.
- Discretion: Comfort with sensitive information about people, finances, and strategy.
Benefits
- Hybrid schedule
- The base salary range for this role is 130,000USD-145,000USD or the equivalent in CAD.
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What This Job Offers
Job Type
Full-time
Career Level
Senior
Education Level
No Education Listed
