About Plenful
Plenful is on a mission to transform healthcare operations from the inside out. Fresh off our $50M Series B and backed by Notable Capital, Bessemer Venture Partners, TQ Ventures, Susa/Kivu Ventures, and other leading investors, we’re building the category-defining AI workflow automation platform that healthcare teams rely on to operate smarter, faster, and more efficiently. Our technology empowers healthcare operators across hospital and health systems, pharmacies and payors to eliminate manual work, reduce administrative burden, and improve compliance, all while unlocking critical revenue to fund programs for their in-need patient populations.
Built by healthcare operators for healthcare operators, Plenful is driven by a deep understanding of the challenges facing today’s care teams. We’re passionate about equipping healthcare workers with world-class tools that deliver real, measurable impact, and we’re proud to serve 60+ leading health systems across the country. If you’re excited to help shape the future of healthcare, we’d love to meet you. Apply now to join our growing team.
About the Role
Plenful is hiring an Executive Assistant to support a senior member of our executive leadership team and create operational leverage across the company. You'll own executive support for your assigned leader, and also coordinate company-wide in-office activities, candidate experiences, and cross-functional operational needs. This role thrives on anticipating needs before they arise, and brings exceptional organization, discretion, and execution to everything it touches. The role is hybrid, based in San Francisco with two days a week in-office.
What You’ll Do
Executive Operations & Calendar Management — Own and optimize your executive's calendar, allocating time across strategic initiatives, customer or board engagements, internal leadership meetings, recruiting, and company priorities. Manage scheduling conflicts, prepare briefing materials, coordinate follow-ups, and act as a trusted gatekeeper for their time.
Travel, Events & Team Coordination — Plan and coordinate domestic and international travel: itineraries, accommodations, transportation, expenses, and logistics. Support leadership offsites, executive meetings, customer visits, and company events, and make sure every participant has a seamless experience.
Candidate & Office Experience — Coordinate onsite candidate interviews across Plenful, partnering with hiring managers and recruiting to create a great candidate experience. Handle interview schedules, office logistics, room bookings, meals, and day-of support. Help keep the in-office environment welcoming and organized during our hybrid week.
You May Be a Fit If
You've spent 8+ years as an in-house Executive Assistant, including 4+ years directly supporting a C-level executive (CEO, CTO, CPO, or similar).
You have a bachelor's degree or equivalent professional experience.
You've supported C-level executives at high-growth technology companies.
You've managed complex executive calendars across multiple stakeholders and time zones.
You've coordinated domestic and international executive travel.
You've partnered with recruiting teams on executive-level or technical hiring.
You manage multiple priorities at once without losing the thread.
You write and speak clearly and confidently.
You handle confidential and sensitive information with discretion.
You know Google Workspace, calendar management systems, travel coordination tools, and modern collaboration platforms well.
Bonus points for experience in healthcare, fintech, or another regulated industry; experience supporting executives at venture-backed or fast-scaling startups; experience coordinating offsites, customer events, or board activities; or familiarity with engineering, product, or technical organizations.
Why You'll Love Working Here
🚀 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 expertise through collaboration with experienced, high-performing leaders across the organization
🏢 Flexible Hybrid Work Environment — We're remote-first, with meaningful office presence in San Francisco and New York. R&D roles follow a hybrid model, with two days per week in our San Francisco office
Benefits & Perks
🏥 Healthcare Coverage — Full medical, dental, and vision insurance for you and participation for your family
💰 401(k) with Company Match — Plenful matches 50% of your first 3% contributed
📊 Equity — Every full-time employee shares in our success
🌴 Unlimited PTO — Take the time you need, when you need it
🍽️ Daily Lunch Stipend — $100/week to cover your midday meals
💪 Wellness Stipend — $100/month to support your health and well-being
🚇 Commuter Benefits — $100/month for SF and NYC-based employees
👶 Parental Leave — Paid leave to support growing families