Executive Assistant

Sesame

$100K — $120K *
Business Services
8 - 10 years of experience
Job Overview by Ladders

Qualifications

  • 10+ years of experience supporting C-suite executives in high-growth startups
  • Proven ability to provide strategic support beyond calendar management
  • Exceptional judgment and problem-solving skills
  • Strong organizational skills with keen attention to detail
  • Excellent interpersonal and communication skills
  • Ability to thrive in dynamic, ambiguous environments and multitask effectively
  • Expertise in Google Workspace, Slack, and other productivity tools
  • Highly educated background preferred, particularly with startups

Responsibilities

  • Manage the CEO's complex calendar and optimize time efficiency
  • Prepare meeting materials, draft agendas, and anticipate scheduling conflicts
  • Serve as a trusted partner to strengthen executive productivity
  • Act as primary contact for stakeholders, maintaining professionalism
  • Plan and manage detailed travel itineraries with proactive issue resolution
  • Handle sensitive information with discretion and professionalism
  • Support seamless business operations in partnership with the Office Manager
  • Assist in driving project initiatives through cross-functional collaboration

Benefits

  • 401 (k) max employer match of 3.5%
  • 100% employer-paid health, vision, and dental coverage for employee and dependents
  • Unlimited PTO and sick time
  • Flexible spending account with employer matching up to $1,650/year
  • Access to Guardian Employee Assistance Program (EAP)
  • Competitive stock options to share in company success
Full Job Description
About the Role

We're looking for a sharp, proactive Executive Assistant to support our CEO and Head of Operations. As a key partner to leadership, you'll manage complex schedules, coordinate high-level communications, and ensure seamless operations in a fast-moving environment. The ideal candidate thrives under pressure, anticipates needs before they arise, and builds strong relationships across teams and external partners. If you're highly organized, adaptable, and excel at making things run smoothly, we want to hear from you!

Key Competencies:
  • Highly Autonomous: Able to navigate complex, ambiguous situations with minimal direction or hand-holding.
  • Proactive & Agile: Stays steps ahead of the executives and the team; pivots seamlessly when priorities shift to ensure everyone remains aligned and on track.
  • Strong Academic/Intellectual Foundation: Highly educated, with critical-thinking skills to process information quickly and strategically.
  • Adaptive Communicator: Highly adaptable to varying situational dynamics, diverse working styles, and cross-functional backgrounds.
  • Strategic Relationship Builder: Focuses on cultivating deep, meaningful relationships across the organization rather than just managing transactional interactions.
Responsibilities:
  • Calendar & Scheduling: Manage the CEO's complex calendar, coordinate meetings, prioritize appointments, and optimize time efficiency.
  • Meeting Preparation & Operational Foresight: Organize materials, draft agendas, and ensure all necessary information is readily available. Anticipate scheduling conflicts and proactively implement solutions before they impact leadership.
  • Executive Partnership: Serve as a trusted partner to executive leadership, helping maximize efficiency, productivity, and organizational effectiveness.
  • Communication Management: Act as a primary point of contact for internal and external stakeholders, handling communications with professionalism, discretion, and sound judgment.
  • Travel Coordination: Plan and manage detailed travel itineraries, including flights, accommodations, and logistics, proactively addressing any issues.
  • Confidentiality & Professionalism: Handle sensitive information with the utmost discretion and professionalism.
  • Operational Support: Partner with the Office Manager to ensure seamless executive support and business operations.
  • Project Assistance: Support key initiatives by collaborating with cross-functional teams to drive efficiency and execution.
Required Qualifications:
  • 10+ years of experience supporting C-suite executives, founders, and senior leadership teams, particularly in high-growth startup environments.
  • Proven track record of providing strategic executive support beyond traditional calendar management.
  • Demonstrated ability to anticipate needs, exercise sound judgment, and independently solve problems.
  • Exceptional organizational skills with meticulous attention to detail and follow-through.
  • Strong interpersonal and communication skills to build rapport across teams and with external partners.
  • Comfortable operating with ambiguity and adapting quickly in a dynamic environment. Ability to multitask in a fast-paced environment with shifting priorities.
  • Expert user of Google Workspace, Slack, and modern business productivity tools.
  • A highly educated background preferred, with a focus on supporting startups.
  • Experience in project management is a plus.

Location: Full-time in-office with flexibility in San Francisco, CA or New York City, NY.

Full-time Employee Benefits:
  • 401 (k) max employer match: 3.5% of compensation
  • 100% employer-paid health, vision, and dental benefits for you and your dependents
  • Unlimited PTO and sick time
  • Flexible spending account with employer matching up to $1,650/year (medical FSA)
  • Guardian Employee Assistance Program (EAP)
  • Opportunity to share in the company's success with competitive stock options

Benefits do not apply to contingent/contract workers.

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