Executive Assistant [Engineering]

About Plenful

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, solving one of the biggest challenges in healthcare today: delayed patient care.
Built by a passionate team of former healthcare operators and world-class AI technologists, Plenful combines deep domain expertise with enterprise-grade technology to automate complex workflows across intake authorization, 340B program optimization, and pharmacy revenue reconciliation. Our AI platform is trusted by 95+ leading healthcare organizations to power smarter, faster, and more resilient pharmacy operations.

Backed by leading investors including Notable Capital, Bessemer Venture Partners, and TQ Ventures, Plenful is building the institutional memory for healthcare and powering the most complex, highest ROI healthcare workflows. We’re actively hiring as we continue to scale.
Learn more about our values and origin story at https://www.plenful.com/company.

The Mandate

Plenful is hiring an Executive Assistant to the Chief Technology Officer to serve as a strategic partner to our technology leadership team and help create exceptional operational leverage across the company. This individual will own executive support for the CTO while also serving as a key coordinator for company-wide in-office activities, candidate experiences, and cross-functional operational needs. The ideal candidate thrives in fast-paced startup environments, anticipates needs before they arise, and brings exceptional organization, discretion, and execution to everything they do.

What You’ll Own

Executive Operations & Calendar Management

Own and optimize the CTO’s calendar, ensuring time is allocated effectively across strategic initiatives, customer engagements, internal leadership meetings, recruiting activities, and company priorities. Proactively manage scheduling conflicts, prepare briefing materials, coordinate follow-ups, and serve as a trusted gatekeeper for the CTO's time.

Travel, Events & Team Coordination

Plan and coordinate domestic and international travel, including itineraries, accommodations, transportation, expense management, and logistics. Support leadership offsites, executive meetings, customer visits, and company events while ensuring a seamless experience for all participants.

Candidate & Office Experience

Serve as a key point of coordination for onsite candidate interviews across Plenful, partnering with hiring managers and recruiting to create an exceptional candidate experience. Coordinate interview schedules, office logistics, room bookings, meals, and day-of support for candidates visiting the office. Help foster a welcoming and organized in-office environment during our hybrid work schedule.

Environment & Technical Context

The Executive Assistant to the CTO will operate within a high-growth, venture-backed healthcare technology company building AI-powered workflow automation solutions for healthcare operations. This role requires strong judgment, exceptional communication skills, and the ability to manage competing priorities across executive leadership, recruiting, and company operations. The position is based in San Francisco and requires in-office presence two days per week.

What Success Looks Like

• The CTO's calendar operates smoothly with minimal scheduling conflicts and strong prioritization.
• Travel and executive logistics are executed flawlessly and proactively.
• Onsite candidates consistently report an exceptional interview experience.
• Leadership meetings, events, and cross-functional initiatives run efficiently and on schedule.
• The CTO and broader leadership team trust you to independently solve problems and manage sensitive matters with discretion.
• You identify opportunities to improve processes and create leverage for executives and teams across the company.

Ideal Background

Must Have

• 8+ years of in-house Executive Assistant experience, including 4+ years directly supporting a Chief Technology Officer (CTO) and/or Chief Product Officer (CPO).
• Bachelor's degree or equivalent professional experience.
• Demonstrated 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 executive-level or technical hiring processes.
• Strong project management and organizational skills with the ability to manage multiple priorities simultaneously.
• Exceptional written and verbal communication skills.
• High degree of discretion and experience handling confidential and sensitive information.
• Deep experience with Google Workspace, calendar management systems, travel coordination tools, and modern collaboration platforms.

Nice to Have

• 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.

Plenful perks

• Comprehensive Benefits Package: Enjoy unlimited PTO, fully covered health insurance (medical, dental, and vision), meal stipend, health & wellness stipend, 401(k) matching, and stock options.
• Mission-Driven, World-Class Team: Join an exceptional group of professionals aligned around a meaningful mission and committed to making an impact.
• Opportunities for Growth: Strengthen your partnership expertise through collaboration with experienced, high-performing leaders across the organization.