Senior Executive Assistant + Business Partner

We’re looking for a seasoned Senior Executive Assistant / Head of Operations who can bring structure, foresight, and follow-through to fast-moving founders and teams — someone who thrives in ambiguity, anticipates needs, and turns ideas into execution.DescriptionRole: Sr. Executive Assistant / Operations ManagerLocation: North America Remote (Canada-based candidates preferred)Type: Full-TimeCompensation: Starting at $75,000.00 - $90,000.00 annuallyAbout Take It Easy GroupTake It Easy is a collective of seasoned Executive Assistants and Chiefs of Staff who thrive in fast-paced, ambiguous environments. We support creative and high-growth founders and look for mission-driven leaders with strategic execution and operational calm to be part of our ecosystem. Our work is grounded in flexibility, trust, and a shared commitment to helping leaders do their best work.About the RoleWe’re hiring a sharp, operations-minded Senior Executive Assistant / Head of Operations to join our growing remote team. This full-time role goes beyond traditional administrative support. You’ll act as a strategic right hand to multiple high-profile clients (founders, C-suite leaders, and entrepreneurs) across diverse industries.You’ll own day-to-day operations, streamline processes, and drive projects to completion. From managing communications and coordinating priorities to building scalable systems, you’ll bring structure and clarity to fast-paced, ever-changing environments.We’re looking for someone based in continental North America (with a preference for Canada-based) who thrives in start-up or professional services settings where priorities shift quickly and no two days look the same.Key ResponsibilitiesProvide proactive executive support: manage calendars, coordinate meetings, book travel, and handle high-level correspondence.Oversee and optimize operations: maintain and improve systems, SOPs, and internal workflows across clients.Drive strategic projects: plan, track, and execute cross-functional initiatives from start to finish.Serve as a trusted partner and gatekeeper: liaise between executives, teams, and external stakeholders with professionalism and discretion.Anticipate needs and eliminate roadblocks: identify process gaps and recommend actionable improvements.Balance competing priorities: manage multiple clients and shifting deliverables with clarity, composure, and accountability.You Might Be a Fit If YouHave 7+ years of experience as a Senior Executive Assistant, Operations Manager, Project Manager, or Chief of Staff.Are based in North America (with a preference for Canada-based).Have supported founders or executive teams in fast-paced, unstructured environments (startups, agencies, or consultancies).Are process-driven yet flexible, able to pivot quickly without losing momentum.Communicate with clarity and polish — both in writing and on Zoom.Can see several steps ahead, anticipating needs, dependencies, and potential roadblocks before they surface.Can own large, complex projects from start to finish, even when given minimal direction — turning ambiguity into action and clarity.Love bringing order to chaos and finding ways to make systems run smoother and smarter.Are tech-savvy, confident using tools like Google Workspace, Slack, Notion, and Asana, AI ToolsTake ownership, operate independently, and thrive when wearing multiple hats.Love bringing order to chaos and finding ways to make systems run smoother and smarter.