Strategic Senior Executive Assistant to C‑Level Leaders

Cypress HCM; San Francisco (CA); On-site; USD 120,000 - 180,000; Full time

Job summary

Cypress HCM in San Francisco seeks an exceptional Executive Assistant to support multiple executives in a fast-growing company. This highly visible role requires proactive, business-minded professionalism who can operate independently with minimal direction and maintain discretion.

The ideal candidate has executive support experience at the highest levels, exercises sound judgment, and can manage complex calendars across global time zones, coordinate meetings and governance activities, and

Qualifications

• 8+ years of Executive Assistant experience supporting C-level executives.
• Experience in fast-paced, high-growth environments.
• Ability to operate independently with minimal direction.

Responsibilities

• Serve as a strategic partner to executives, proactively anticipating needs and ensuring efficient execution of priorities.
• Manage highly complex and sensitive calendars across multiple global time zones, balancing competing priorities while partnering with senior leaders and EAs across the organization.
• Prioritize and manage multiple competing demands with a strong sense of urgency and a consistently proactive, one-step-ahead approach.
• Handle highly confidential information with discretion and professionalism.
• Coordinate and execute leadership team meetings, operating reviews, planning sessions, and strategic discussions.
• Prepare presentation materials, templates, agendas, and supporting documentation for executive, Board, and leadership meetings.
• Capture meeting notes, track action items, monitor deliverables, and follow up on commitments and OKRs.
• Partner with internal and external stakeholders to coordinate Board meetings and governance-related activities, ensuring deadlines and deliverables are met.
• Create, document, and continuously improve workflows, processes, and operating mechanisms that increase organizational efficiency and executive effectiveness.
• Identify process gaps and recommend scalable solutions that improve communication, coordination, and operational effectiveness as the company grows.
• Provide administrative support to executives and selected members of the strategic finance leadership team.
• Manage expense reporting, including international and multi-currency expenses.
• Support team drives, contact management systems, organizational records, and administrative processes.
• Partner closely with the CEO's Executive Assistant and broader Executive Assistant community to ensure alignment across executive priorities and company initiatives.
• Serve as an active and visible leader within the Executive Assistant community by building strong partnerships, sharing best practices, and contributing to a culture of excellence across the executive support organization.

Skills

Executive presence

Communication skills

Relationship-building

Organizational skills

Decision making / business judgment

Job description

Cypress HCM in San Francisco seeks an exceptional Executive Assistant to support multiple executives in a fast-growing company. This highly visible role requires proactive, business-minded professionalism who can operate independently with minimal direction and maintain discretion.

The ideal candidate has executive support experience at the highest levels, exercises sound judgment, and can manage complex calendars across global time zones, coordinate meetings and governance activities, and