Executive Assistant

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 90+ 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.

Plenful is hiring an Executive Assistant & Office Manager to support our CEO and CTO while running the day-to-day of our San Francisco office. You'll own executive calendars and travel for both leaders, and the experience of everyone who walks through our door — teammates, candidates, and visitors alike. The role is hybrid, in our San Francisco office three days a week.

• Executive Support Own and optimize calendars and travel for the CEO and CTO — prioritizing strategic work, customer engagements, and company priorities, and coordinating domestic and international travel logistics.

  Office & Teammate Experience Keep the physical space running — supplies, vendor relationships, facilities issues, deliveries — and own the moments that make coming into the office worth it: team lunches, snack stock, seating and space planning, and onboarding setup for new hires.

  Candidate & Visitor Experience Coordinate onsite interview logistics — scheduling, room bookings, meals, and day-of hosting — partnering with recruiting and hiring managers to keep this consistent as hiring scales.

  Events, Culture & Vendor Management Plan in-office events, offsites, and team celebrations. Manage vendor relationships and own the office spend budget, tracking costs as the team grows.

• 5–8 years of experience combining executive support and office/workplace operations, including direct experience supporting a senior leader (CEO, CTO, CPO, or equivalent).

• Proven success managing complex executive calendars and travel across multiple stakeholders and time zones.

• Track record managing multiple vendors and priorities simultaneously without things falling through the cracks.

• Experience coordinating candidate or visitor logistics at scale.

• Strong written and verbal communication skills, with a high degree of discretion handling confidential information.

• Comfortable with ambiguity — this role will grow and shift as the company scales.

Nice to Have

• Experience supporting two or more executives simultaneously.

• Experience at an early-stage or high-growth startup.

• Experience in healthcare, fintech, or other regulated industries.

• 🚀 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

• 🏥 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