Executive Assistant

Cypress HCM; Menlo Park (CA); Hybrid; USD 120,000 - 180,000; Full time

Job summary

Cypress HCM is seeking an experienced Executive Assistant to provide flexible administrative and operational support across its Product organization. This floater role supports multiple executives, with a focus on Directors and Senior Directors and occasional VP-level work.

The position requires adaptability, proactive organization, and the ability to learn different executive preferences quickly. Hybrid work with onsite presence in Menlo Park, with potential for up to 5 days onsite based on

Qualifications

• Approximately 10 years of executive administrative support experience.
• Experience supporting multiple executives simultaneously in floater/shared environments.
• Experience supporting Directors, Senior Directors, or VP-level leadership.
• Background in a mid-to-large technology company, preferably fast-growing.
• Adapt quickly to changing structures, priorities, and executive preferences.
• Strong calendar management, travel coordination, expense reporting, and meeting organization skills.

Responsibilities

• Provide administrative and executive support to multiple leaders across the Product organization.
• Manage complex calendars, schedule meetings, coordinate competing priorities, and optimize executive time.
• Coordinate domestic and international travel, expense reporting, and other executive needs.
• Provide temporary coverage for executive assistants during vacations, leaves, and peak workload periods.
• Learn individual executive preferences and team processes quickly when transitioning between assignments.
• Coordinate team meetings, product reviews, leadership meetings, and steering committees.
• Build trackers, meeting schedules, and tools to improve prioritization and efficiency.
• Partner with Product Managers, Engineers, Customer Experience, and cross-functional stakeholders.
• Streamline administrative processes, improve meeting effectiveness, and anticipate executive needs.
• Organize team events, maintenance of shared folders, and interview logistics.
• Use AI tools and productivity workflows to summarize meetings and track action items.

Skills

Executive support

Calendar management

Travel coordination

Cross-functional collaboration

Organizational skills

Discretion

Job description

Work Arrangement

Hybrid, currently 3 days onsite per week. Must be flexible to work onsite up to 5 days per week depending on executive schedules.

Job Description

We are seeking an experienced Executive Assistant to provide flexible administrative and operational support across its Product organization. This role will serve as an administrative floater, supporting approximately three executives at a time, with a maximum of four.

You will primarily support Directors and Senior Directors, with occasional VP-level support. Assignments may vary from a few days to several months depending on business needs, executive coverage, team transitions, and changing priorities.

The ideal candidate is adaptable, proactive, highly organized, and comfortable stepping into unfamiliar teams and learning different executive preferences quickly. This person should be able to manage traditional executive administrative responsibilities while also supporting operational activities that help Product teams work more efficiently.

Responsibilities

• Provide administrative and executive support to multiple leaders across our Product organization.
• Manage complex calendars, schedule meetings, coordinate competing priorities, and proactively optimize executive time.
• Coordinate domestic and international travel, expense reporting, and other executive administrative needs.
• Provide temporary coverage for executive assistants during vacations, leaves, hiring transitions, and periods of increased workload.
• Quickly learn individual executive preferences, team processes, and business priorities when transitioning between assignments.
• Coordinate team meetings, Product reviews, business reviews, steering committees, and leadership meetings.
• Build and maintain trackers, meeting schedules, and organizational tools to improve prioritization and operational efficiency.
• Partner with Product Managers, Engineers, Customer Experience teams, and other cross-functional stakeholders.
• Help streamline administrative processes, improve meeting effectiveness, and anticipate the needs of supported executives.
• Organize team events, maintain shared folders and documentation, and coordinate visitor and interview logistics.
• Use AI tools and productivity workflows to streamline communications, summarize meetings, track action items, and improve administrative efficiency.

Qualifications

• Approximately 10 years of relevant executive administrative support experience preferred.
• Demonstrated experience supporting multiple executives simultaneously, ideally in a floater, backup, or shared-support environment.
• Experience supporting Directors, Senior Directors, or VP-level leadership.
• Background in a mid-to-large technology company, preferably within a fast-growing or evolving organization.
• Proven ability to adapt quickly to changing organizational structures, priorities, and executive preferences.
• Experience supporting Product, Engineering, Customer Experience, or other cross-functional business teams preferred.
• Strong operational and project coordination skills beyond traditional administrative responsibilities.
• Excellent calendar management, travel coordination, expense reporting, and meeting organization skills.
• Strong judgment, communication, discretion, attention to detail, and interpersonal skills.
• Demonstrated employment stability and the ability to build productive long-term working relationships.
• Comfortable working onsite in Menlo Park 3 days per week, with flexibility to increase to 5 days depending on executive schedules.