Executive Assistant [Engineering]

Plenful•San Francisco, CA

8d•Hybrid

About The Position

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. 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.

Requirements

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 Haves

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.

Responsibilities

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.
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.
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.
Identify opportunities to improve processes and create leverage for executives and teams across the company.