Executive Assistant

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 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.

About the Role

We're hiring an Executive Assistant to support our CPO directly. This is a high-trust, high-context role — you'll manage the calendar, communications, and logistics of someone setting product direction for a fast-moving company, and you'll need the judgment to know what needs the CPO's attention and what doesn't.

You've done this before. You know what it means to sit close to a product leader: the rhythm of roadmap reviews, customer calls, and cross-functional syncs, and how to protect focus time without creating bottlenecks. Note: This role is based in NYC and requires in-office presence a minimum of 3 days per week.

What You’ll Do

Calendar & time management Own the CPO's calendar end to end — prioritizing customer engagements, leadership syncs, and roadmap work, and pushing back on meetings that don't earn their place on the calendar.

• Travel & logistics Coordinate domestic and international travel, adjusting in real time when plans change.

• Communication & coordination Draft and manage correspondence, prep materials for meetings, and coordinate across product, engineering, and design leadership to keep information moving.

• Meeting & event support Plan and run logistics for product offsites, leadership meetings, and team events. This person will also own the operations of the New York office.

• Confidentiality & judgment Handle sensitive product, personnel, and strategic information with discretion. Exercise independent judgment on what requires escalation.

You May Be a Fit If

Must have

• 6+ years as an Executive Assistant, including direct experience supporting a product leader (CPO, VP Product, Head of Product, or equivalent).

• A track record managing complex calendars and multi-leg domestic/international travel.

• Strong written and verbal communication.

• High discretion with confidential product and company information.

• Based in the NYC area, available in-office 3 days/week.

• Comfortable with ambiguity — this role will shift as we scale.

• Comfortable using AI tools (ChatGPT, Claude, etc.) to move faster on research, scheduling, and communication — you look for where AI can take work off your plate, not just where you're told to use it.

Nice to have

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

• Experience in healthcare, fintech, or another regulated industry.

• Experience supporting a product org through a scaling phase — new hires, org changes, process build-out.

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