Executive Assistant

Responsibilities

• Own and optimize the CTO’s calendar, ensuring effective time allocation across strategic initiatives, customer engagements, and internal leadership meetings.
• Proactively manage scheduling conflicts, prepare briefing materials, and serve as a trusted gatekeeper for the CTO's time.
• Plan and coordinate domestic and international travel, including itineraries, accommodations, transportation, and expense management.
• Support leadership offsites, executive meetings, customer visits, and company events.
• Partner with recruiting teams to coordinate onsite candidate interviews and ensure an exceptional candidate experience.
• Help foster a welcoming and organized in-office environment during our hybrid work schedule.

Requirements

• 8+ years of in-house Executive Assistant experience.
• 4+ years directly supporting a Chief Technology Officer (CTO) and/or Chief Product Officer (CPO).
• Experience supporting C-level executives in high-growth technology companies.
• Proven success managing complex executive calendars across multiple stakeholders and time zones.
• Extensive experience coordinating domestic and international executive travel.
• Experience partnering with recruiting teams to coordinate technical hiring processes.
• Proficiency in Google Workspace and modern collaboration platforms.
• Bachelor's degree or equivalent professional experience.
• High degree of discretion and experience handling confidential information.

Preferred Qualifications

• Experience in healthcare, fintech, or other highly regulated technology environments.
• Experience supporting executives at venture-backed startups or rapidly scaling companies.
• Experience coordinating executive offsites, customer events, or board-related activities.
• Familiarity with engineering, product, or technical organizations.

Benefits

• Comprehensive benefits package including unlimited PTO.
• Fully covered health insurance (medical, dental, and vision).
• Meal stipend and health & wellness stipend.
• 401(k) matching and stock options.

About the Company

Plenful is on a mission to move pharmacy forward through intelligent automation. We build AI-powered software that eliminates administrative burden, strengthens compliance, and unlocks revenue across critical pharmacy workflows. Backed by leading investors including Notable Capital and Bessemer Venture Partners, Plenful is building the institutional memory for healthcare.