Sr. Executive Assistant

Cypress HCM; Menlo Park (CA); On-site; USD 90,000 - 140,000; Full time

Job summary

Cypress HCM is seeking an exceptional Executive Assistant to support multiple executives in a fast-paced, high-growth environment. This role requires proactivity, strong business judgment, and the ability to operate independently with minimal direction.

The ideal candidate has executive support experience at the highest levels, exercises discretion, and demonstrates ownership. They will handle confidential information and drive alignment across the executive team as the company scales.

Qualifications

• 8+ years of Executive Assistant experience supporting C-level executives.
• Experience in fast-paced, high-growth environments.
• Ability to act with discretion and ownership.
• Strong judgment and decision-making when guidance is unavailable.
• Experience supporting growth, IPO readiness, or public company operations preferred.

Responsibilities

• Serve as a strategic partner to executives, proactively anticipating needs and ensuring efficient execution of priorities.
• Manage calendars across multiple global time zones with senior leaders and Executive Assistants.
• Coordinate leadership team meetings, operating reviews, planning sessions, and strategic discussions.
• Prepare presentation materials, templates, agendas, and 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 activities.
• Create, document, and improve workflows to increase organizational efficiency and executive effectiveness.
• Identify process gaps and recommend scalable solutions as the company grows.

Skills

Executive support

Calendar management

Discretion

Stakeholder management

Board coordination

Job description

Seeking an exceptional Executive Assistant to support multiple executives. This is a highly visible role requiring a proactive, business-minded professional who thrives in a fast-paced, high-growth environment and can operate independently with minimal direction.

The ideal candidate brings executive support experience at the highest levels, exercises exceptional judgment, and consistently operates with professionalism, discretion, and a strong sense of ownership. They are comfortable making informed decisions and moving work forward when executive guidance is unavailable, using sound business judgment and a deep understanding of organizational priorities.

Responsibilities

Executive Support

• 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 closely with senior leaders and Executive Assistants 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 the utmost discretion and professionalism.

Meeting & Business Operations

• 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.

Team & Administrative Support

• 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.

Qualifications

• 8+ years of Executive Assistant experience supporting C-level executives, Presidents, COOs, founders, or senior finance leaders.


• Experience supporting senior executives in investment banking, private equity, venture capital, public company finance organizations, management consulting, or high-growth technology companies.


• Proven ability to operate with the pace, precision, responsiveness, and attention to detail expected in demanding financial services or executive environments.


• Demonstrated ability to make sound decisions, navigate ambiguity, and move work forward independently when executive guidance is unavailable.


• Experience supporting organizations through significant growth, transformation, IPO readiness, or public company operations strongly preferred.


• Proven ability to influence stakeholders, drive accountability, and achieve outcomes across functions and levels of seniority without direct authority.


• Strong executive presence and demonstrated success interacting with senior executives, Board members, investors, auditors, and external partners.


• Exceptional communication, organizational, and relationship-building skills.


• Process-oriented mindset with a track record of identifying inefficiencies and implementing scalable solutions.


• Comfortable working with urgency and occasional needs outside traditional business hours.

What Success Looks Like

• Executive schedules, meetings, travel, communications, and stakeholder interactions run seamlessly despite changing priorities and limited executive availability.


• Scalable processes, operating rhythms, and support mechanisms are implemented to support the company's continued growth and future public company needs.


• Strong partnerships are established across the executive team, Board stakeholders, and the Executive Assistant community.


• The Executive Assistant is viewed as a trusted advisor, effective operator, and highly credible representative