Executive Assistant

About Plenful

Plenful is dedicated to advancing pharmacy by harnessing intelligent automation. The company develops AI-driven software that minimizes administrative tasks, ensures compliance, and enhances revenue in critical pharmacy workflows — addressing the prevalent challenge of delayed patient care. Founded by healthcare experts and top AI technologists, Plenful automates complex processes like intake authorization, 340B program optimization, and pharmacy revenue reconciliation. Its AI solutions are trusted by over 95 leading healthcare organizations to streamline pharmacy operations.

Supported by prominent investors such as Notable Capital, Bessemer Venture Partners, and TQ Ventures, Plenful is building foundational technology for healthcare, focusing on the most impactful and high-return workflows. As the company scales, it is actively expanding its team.

Role Overview

We are seeking an Executive Assistant to provide high-level support to a senior executive and foster operational efficiency throughout the organization. This role will manage executive support responsibilities while coordinating company-wide events, candidate experiences, and cross-departmental operational efforts. The candidate should excel in dynamic startup settings, anticipate needs proactively, and demonstrate exceptional organizational skills, discretion, and execution.

Key Responsibilities

• Manage and optimize the executive’s calendar ensuring strategic priorities, customer and board meetings, leadership discussions, recruiting, and company goals are balanced effectively.
• Handle scheduling conflicts, prepare briefing documents, coordinate follow-up actions, and act as a trusted gatekeeper for the executive's time.
• Coordinate domestic and international travel arrangements including itinerary planning, accommodations, transport, expense handling, and logistics.
• Support leadership offsites, executive meetings, customer visits, and company-wide events ensuring seamless coordination.
• Serve as the primary liaison for coordinating onsite candidate interviews, collaborating with hiring managers and recruiting teams to provide an outstanding candidate experience.
• Manage interview schedules, office logistics, meeting spaces, catering, and on-site support to uphold a welcoming and organized physical office environment during hybrid work schedules.
• Work with high judgment in a rapidly growing healthcare technology environment, balancing competing priorities involving executive leadership, recruiting, and operational teams.
• Be present onsite in San Francisco two days per week to facilitate in-office activities.

Success Indicators

• Executive’s calendar is managed efficiently with minimal conflicts and well-prioritized engagements.
• Travel and logistical arrangements are consistently executed proactively and without issues.
• Candidates report remarkable interview experiences during onsite visits.
• Leadership meetings, events, and cross-functional initiatives operate smoothly and on schedule.
• Executives and leadership place their trust in your ability to handle sensitive matters discreetly and solve problems independently.
• You identify and implement process improvements that enhance productivity and operational leverage across the organization.

Qualifications

• At least 8 years of in-house Executive Assistant experience, with 4 or more years supporting C-level executives such as CEO, CTO, or CPO.
• Bachelor’s degree or comparable professional background.
• Demonstrated ability supporting C-suite leaders within high-growth tech companies.
• Skilled in managing complex calendars across multiple stakeholders and time zones.
• Proficient in coordinating both domestic and international executive travel.
• Experienced in partnering with recruiting teams for executive or technical hiring processes.
• Strong project management capabilities with the ability to juggle multiple priorities.
• Excellent written and oral communication skills.
• High discretion and experience managing confidential information.
• Advanced use of Google Workspace, calendar management tools, travel coordination software, and modern collaboration platforms.

Preferred Experience

• Background in healthcare, fintech, or other regulated technology sectors.
• Experience supporting executives in venture-backed startups or rapidly scaling organizations.
• Familiarity with organizing executive offsites, customer events, or board meetings.
• Understanding of engineering, product, or technical teams, particularly in support of technical leadership.

Benefits and Workplace Environment

• Comprehensive benefits including unlimited paid time off, fully covered medical/dental/vision insurance, meal and wellness stipends, 401(k) matching, and stock options.
• Be part of a mission-driven, elite team committed to making a significant impact in healthcare.
• Opportunity for professional growth through collaboration with experienced leaders.
• Flexible hybrid work setup with two days per week onsite at the downtown San Francisco office (Monday and Wednesday).