We are seeking a highly organized and proactive Executive Assistant to support the CEO of a fast-growing AI and health technology company. This role is central to enabling the CEO to focus on strategic priorities by expertly managing time, calendars, and logistics in a dynamic, innovation-driven environment. The ideal candidate thrives in a fast-paced setting, and brings strong judgment, discretion, and operational excellence. This is a hands-on, high-ownership role at an early-stage startup, and responsibilities may expand and evolve over time.

What You’ll Do
Executive Time & Calendar Management

Own and manage the CEO's complex calendar, including scheduling, rescheduling, and prioritizing meetings across multiple time zones

Act as a strategic gatekeeper for meeting requests, aligning executive time with business and product priorities

Prepare daily and weekly agendas to ensure the CEO is well-prepared for meetings and key milestones

Proactively update the calendar around travel, blocking time and adjusting meetings as soon as flights or trips are booked

Meetings, Conferences & Offsites

Manage conference planning and booking, including registrations, travel, accommodations, agendas, and post-event follow-ups

Coordinate travel arrangements, including flights, hotels, and ground transportation, for the CEO and, at times, other members of the executive team

Prepare a pre-trip briefing summarizing key travel and meeting details ahead of each trip

Support planning and execution of company offsites, including on-site and out-of-town travel as needed

Partner with internal teams, vendors, and event organizers to ensure seamless execution

Administrative & Operational Support

Draft, edit, and manage correspondence, calendars, and meeting materials

Organize and maintain the CEO's inbox for clarity and follow-up

Maintain organized records, contacts, and documentation with a high degree of accuracy

Handle confidential and sensitive information related to leadership, strategy,



and partnerships

Provide light office support as needed (e.g., restocking supplies, coordinating with office vendors, keeping shared spaces organized) as the Toronto team grows

Support ad hoc projects and operational initiatives in a rapidly evolving AI and health tech workplace

What You’ll Bring

2-5+ years of experience as an Executive Assistant or in a similar administrative/coordination role; experience in tech or SaaS environments is a plus

Exceptional organizational and time-management skills with the ability to manage competing priorities

Strong attention to detail and follow-through in a fast-paced setting

Excellent written and verbal communication skills

High level of professionalism, discretion, and sound judgment

Proficiency with modern productivity tools (e.g., Google Workspace, Outlook, Slack, Zoom)

Comfort and enthusiasm with AI tools, and a willingness to learn and adopt new workflows

Ability to produce polished, accurate work independently - including drafting communications that require minimal to no review or editing before being sent

A proactive, high-initiative approach to identifying and completing tasks without needing to be asked

Competitive salary and equity in a high-growth startup

Hybrid work, out of our Downtown Toronto office

Flexible PTO, take what you need

Medical, dental, and vision coverage

Great startup culture, including company off-sites

High-achieving team, including ex-Amazon engineers and alumni of Bain, BCG, Goldman Sachs, and more

Only the best belong here
We are unapologetic about talent.



This should be the best team you have ever been on. Protecting that standard is how we honor each other’s time, ambition, and craft.

We work even harder to keep our partners than we did to earn them initially
The work does not stop when a customer first onboards to our platform. It deepens over time. We partner with operators, listening and learning about real problems, and translate that into solutions that help them succeed in practice. We earn trust through consistent delivery.

We keep the patient downstream of every decision
At the end of the day, this is about the patient. We get there by deeply respecting and reflecting on our purpose: to develop software that aids teams in delivering better care.

Raise the bar on ownership
We grow because people here go beyond the minimum. We invest extra effort, care, and ownership into what we build.

The world is moving fast. We move faster.
This is a race. We work hard, we move early, and we stay ahead of problems and competitors. If we slow down, someone else will pass us.

We say what’s true, early, and we keep communication direct and clean so the team can move.

Bring good vibes and win together
We win as a team. We bring energy, support each other, and make the workplace somewhere people are excited to show up.

#LI-Hybrid

About ExaCare AI
ExaCare AI is a leading health tech company on a mission to build the AI operating system for post-acute care. Our platform turns messy, unstructured referral packets into clear clinical insights and next steps, so teams can make faster, safer placement decisions with less administrative burden. Today, ExaCare AI powers more than 1,500 facilities, and is growing rapidly.

We recently raised a $30M Series A led by Insight Partners, and are bringing world-class talent together to transform healthcare. If you like building, learning, and want to make a real impact, come join us!

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📌 Executive Assistant (Ontario)
🏢 ExaCare AI
📍 Ontario