About Stewardly

Stewardly 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 Role

We'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 Do

Own the CEO's calendar end-to-end — prioritize ruthlessly, batch where possible, protect deep work, and surface the trade-offs when they matter
Triage inbox and inbound: filter signal from noise, draft replies in the CEO's voice, escalate only what needs to be escalated
Coordinate complex domestic and international travel, including itineraries, logistics, and contingency planning
Prepare the executive team for every meeting that matters: agendas, briefing docs, context on the people in the room, clear next steps after
Manage expenses, reimbursements, vendor relationships, and the operational small-stuff that quietly compounds
Plan and execute team offsites, leadership gatherings, and the occasional high-stakes dinner or event
Project-manage cross-functional initiatives that the CEO is driving but doesn't have the bandwidth to coordinate
Hold confidentiality without exception — you'll see board materials, financials, personnel decisions, and personal matters
Build the systems and rituals (weekly reviews, prep cadences, follow-up loops) that scale as the company does

What You Bring

4+ years supporting senior executives, ideally a founder or C-suite leader at a startup or high-growth company
Demonstrated judgment under ambiguity — you can tell us about a time you made a call without being asked and got it right
Excellent written communication; you can draft in someone else's voice and have it land cleanly
Deep fluency in modern productivity stacks (Google Workspace, Slack, Notion, calendar tooling) and a real point of view on how to use them
Operational rigor: you build systems, run them tightly, and know when to evolve them
Discretion that is non-negotiable — you've handled sensitive information and have references who'll confirm it
High agency, low ego — comfortable with the unglamorous work and proud of the leverage it creates
Based in North America and able to work core hours that overlap with a U.S.-based team

Bonus Points

Experience at an early- to growth-stage startup where the role evolved as the company scaled
Background supporting executives in healthcare, B2B SaaS, or a regulated industry
Chief of Staff–adjacent experience: light project management, board prep, or investor relations support
Comfort with travel coordination tools, expense platforms (Brex, Ramp, Expensify), and modern admin tooling
A clear personal philosophy on how to support an executive — you've thought about this and can articulate it

Why Stewardly

Mission that matters: we're building infrastructure for the people doing the hardest work in healthcare
Real ownership, real impact: small team, big mandate, fast decisions
Competitive 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 thinking
A 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 person

How to Apply

Send 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.

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Executive Assistant

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