Pippen AI is a rapidly growing healthcare tech startup with the mission to solve the paperwork problem for family doctors. As a certified AI Scribe vendor with OntarioMD and Canada Health Infoway, we support clinicians across Canada. Our vision is to make healthcare professionals’ lives easier by taking administrative tasks off their plates so they can focus on patient care.

The Role

We are looking for a motivated, coachable, and proactive Executive Assistant to support both our CEO and COO. We highly value the ability to execute on our vision with speed and ownership to deliver on tasks end-to-end. This role is a unique opportunity to elevate your skillset and grow with us as we scale.

How You Will Make and Impact

Working closely with the CEO and COO, you will be providing hands-on, execution-focused support to help them stay focused and organized. You will help clarify priorities, unblock barriers, and ensure tasks are completed. Being able to follow-up on projects and close the loops will directly impact how the leadership team performs and achieves the company's mission.

Key Responsibilities

Calendar & Scheduling

• Manage the calendars for the CEO and COO using strong judgment around priorities
• Organize schedules to reflect real business priorities, not just meeting requests
• Protect time for deep work, preparation, and critical deliverables
• Project Coordination: Keep our Trello boards up to date and ensure projects stay on track.

Task Management & Execution

• Actively track commitments, deadlines, and unfinished work across multiple channels (email, Slack, Trello, CRM, meetings)
• Break down vague or incomplete requests into clear next steps and move them forward independently
• Maintain reliable systems so tasks, decisions, and loose ends stay visible and nothing gets dropped
• Follow up consistently to ensure execution and closure, especially in a fast-moving environment

Client & External Communication

• Coordinate and follow up on demos and meetings with physicians, clinicians, and healthcare organizations
• Draft and send professional communications on behalf of leadership when appropriate
• Ensure timely follow-ups so opportunities and relationships do not stall

Communication & Prep Support

• Help triage inboxes and flag time-sensitive or high-priority items
• Draft clear, concise emails and messages that reflect executive intent and tone
• Prepare meeting materials such as agendas, summaries, and context when needed

Research, Conferences & Logistics

• Conduct light research on conferences, vendors, tools, and opportunities
• Support conference planning and occasionally attend conferences (typically spring and fall)
• Assist with bookings, logistics, and preparation related to events and travel

What We’re Looking For

• Highly motivated, coachable, and eager to grow in a fast-paced startup environment
• Strong sense of ownership with the ability to execute tasks end-to-end
• Comfortable exercising judgment, making progress independently, and asking clarifying questions when needed
• Organized, reliable, and detail-oriented
• Comfortable using (or learning) tools such as Slack, Trello, CRM systems; interest or experience in AI is a strong asset

Why Join Us?

• Impact: Be part of a mission-driven company improving healthcare workflows.
• Growth and Learning: You’ll gain hands-on experience working directly with the CEO and COO of a growing healthcare AI company. You will develop skills in prioritization, execution, communication, client coordination, and operational leadership, with increasing responsibility as trust and capacity grow.
• Flexible Work: Enjoy a flexible work environment with a mix of remote work and in-person collaboration (office space in Toronto).

If you enjoy bringing structure to complexity, following through on details, and helping leaders operate at their best, we would love to hear from you.