Executive Assistant
About StewardlyStewardly is building the clinical intelligence platform for mental health. We're a funded startup with the kind of traction growth that makes the next twelve months pivotal — serving therapists, psychologists, and psychiatrists across the country, and at the stage where every hire shapes the trajectory of the company. If you want to build something that matters in a space that's been overdue for real innovation, this is the room to be in.The RoleWe're hiring an Executive Assistant who treats this work as a craft. You'll be a force multiplier for our CEO and leadership team — the person who creates the conditions for them to do their highest-leverage work. That means anticipating two moves ahead, protecting focus ruthlessly, and operating with the kind of judgment that earns trust on day one.This is not a calendar role. The calendar is the easy part. The hard part is knowing which meeting matters, which email needs a real answer versus a holding reply, which travel can be combined, which fire is actually a fire, and when to interrupt the CEO versus when to handle it yourself.We don't want someone executing tasks. We want an operator.This is a fully remote role, open to candidates anywhere in North America.What You'll DoOwn the CEO's calendar end-to-end — prioritize ruthlessly, batch where possible, protect deep work, and surface the trade-offs when they matterTriage inbox and inbound: filter signal from noise, draft replies in the CEO's voice, escalate only what needs to be escalatedCoordinate complex domestic and international travel, including itineraries, logistics, and contingency planningPrepare the executive team for every meeting that matters: agendas, briefing docs, context on the people in the room, clear next steps afterManage expenses, reimbursements, vendor relationships, and the operational small-stuff that quietly compoundsPlan and execute team offsites, leadership gatherings, and the occasional high-stakes dinner or eventProject-manage cross-functional initiatives that the CEO is driving but doesn't have the bandwidth to coordinateHold confidentiality without exception — you'll see board materials, financials, personnel decisions, and personal mattersBuild the systems and rituals (weekly reviews, prep cadences, follow-up loops) that scale as the company doesWhat You Bring4+ years supporting senior executives, ideally a founder or C-suite leader at a startup or high-growth companyDemonstrated judgment under ambiguity — you can tell us about a time you made a call without being asked and got it rightExcellent written communication; you can draft in someone else's voice and have it land cleanlyDeep fluency in modern productivity stacks (Google Workspace, Slack, Notion, calendar tooling) and a real point of view on how to use themOperational rigor: you build systems, run them tightly, and know when to evolve themDiscretion that is non-negotiable — you've handled sensitive information and have references who'll confirm itHigh agency, low ego — comfortable with the unglamorous work and proud of the leverage it createsBased in North America and able to work core hours that overlap with a U.S.-based teamBonus PointsExperience at an early- to growth-stage startup where the role evolved as the company scaledBackground supporting executives in healthcare, B2B SaaS, or a regulated industryChief of Staff–adjacent experience: light project management, board prep, or investor relations supportComfort with travel coordination tools, expense platforms (Brex, Ramp, Expensify), and modern admin toolingA clear personal philosophy on how to support an executive — you've thought about this and can articulate itWhy StewardlyMission that matters: we're building infrastructure for the people doing the hardest work in healthcareReal ownership, real impact: small team, big mandate, fast decisionsCompetitive comp, meaningful equity, and working with a team that values work-life balance Fully remote, North America–wide — work from wherever you do your best thinkingA growth trajectory that creates outsized opportunity for the people who get in early — including a clear path toward Chief of Staff or operational leadership for the right personHow to ApplySend us a short note covering three things: a moment you anticipated an executive's need before being asked and what you did about it, the productivity or operating system you rely on (tools, rituals, anything), and one thing you'd want to change in the first 30 days of supporting a new executive. Include your LinkedIn or resume. We read everything.Stewardly is an equal opportunity employer. We welcome applicants of all backgrounds and identities.