Senior Executive Assistant

Handshake was founded on a simple belief that everyone deserves a path to a great career, regardless of where they went to school or who they know. Today, we power 25 million job seekers, 1 million+ employers, and 1,600 educational institutions.

In 2025, we started Handshake AI and built the fastest-growing AI data business in history. We work directly with frontier AI lab researchers to create evaluations, publish benchmarks, and push the boundary of data. We’ve grown from $0 to ~$1B run rate and pay ~$60M to over 30K individuals every month.

Handshake is seeking a highly organized, proactive, and strategic Senior Executive Assistant to support three C-level executives. This role is critical to ensuring our leaders operate efficiently and effectively, enabling them to focus on driving the business forward.

The ideal candidate thrives in a fast-paced environment, exercises exceptional judgment and discretion, anticipates needs before they arise, and seamlessly manages competing priorities. In addition to providing executive support, this individual will serve as a trusted partner across the organization, helping coordinate key initiatives, drive operational excellence, and foster a positive employee experience.

This position is based in downtown San Francisco and requires an in-office presence five days per week (Monday–Friday).

• Complex calendar management and internal and external meeting coordination across three C-level executives, balancing competing priorities and maximizing executive effectiveness.

• Schedule internal and external meetings; follow up with guests to confirm attendance and help compile and prepare meeting materials.

• Assist with booking travel, including airline and hotel, and ground transportation arrangements, and prepare detailed itineraries for executives.

• Manage expenses and expense reporting for executive leaders.

• Act as a strategic partner to executives by anticipating needs, proactively solving problems, and identifying opportunities to improve efficiency and streamline operations.

• Support special projects and cross-functional initiatives on behalf of executive leaders, tracking key deliverables, deadlines, and follow-up items.

• Plan team events, offsites, and annual week-long onsite while maintaining a strong pulse on culture and team morale.

• Act as the team expert and go-to person for matters related to supported leaders and departments.

• Work closely with the recruiting team to coordinate interviews between executives, team members, and candidates, ensuring a seamless candidate experience.

• Serve as a welcoming representative of Handshake for executive guests, candidates, partners, and other visitors to the San Francisco office, ensuring a polished and professional experience.

• Coordinate meeting logistics, room setup, and executive hospitality for leadership meetings and key visitors.

• Keep relevant stakeholders informed and ensure information is effectively communicated throughout teams and the broader organization. Identify communication gaps and escalate issues when appropriate.

• Leverage technology, AI-powered tools, and process improvements to increase efficiency, automate routine tasks, and enhance executive support workflows.

• Exercise exceptional judgment and discretion while handling confidential business, personnel, and organizational matters.

• Collaborate closely with the broader Executive Assistant team, sharing best practices and providing support as needed.

• 5+ years of Executive Assistant experience supporting senior executives, preferably within a high-growth technology company or similarly fast-paced environment.

• Proven experience supporting multiple senior leaders simultaneously with exceptional attention to detail and prioritization skills.

• Outstanding verbal and written communication skills.

• Exceptional organizational and project management abilities with a strong bias toward action.

• Demonstrated ability to exercise sound judgment, maintain confidentiality, and navigate sensitive situations with discretion.

• High emotional intelligence and strong interpersonal skills, with the ability to build trust and influence across all levels of the organization.

• Resourceful, adaptable, and comfortable operating in ambiguity.

• Experience planning complex travel, offsites, team events, and executive meetings.

• Strong proficiency in Google Workspace and collaboration tools such as Slack, Zoom, Workday, and modern productivity platforms.

• Experience leveraging AI and automation tools to improve efficiency and streamline administrative workflows is a plus.

• Team-oriented mindset with a willingness to collaborate, share best practices, and support fellow members of the Executive Assistant team.

• Passion for problem-solving, continuous improvement, and delivering exceptional support.