About the Role 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 environment 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 Benefits + Perks: 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

An insight into our Core Values

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.

Radical candor, zero politics 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.

If this sounds like you, we'd love to have a chat!

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