Executive Assistant- CEO/CTO/COO

Pearl; West Hollywood (CA); Hybrid; USD 90,000 - 130,000; Full time

Benefits offered by this job

Stock options

Hybrid schedule

Uncapped PTO

Professional development

Job summary

Pearl is seeking a proactive Executive Assistant to support our CEO, CTO, and COO. You will own complex calendars, coordinate travel and events, prepare materials for board and leadership meetings, and manage the day-to-day operations of our West Hollywood office.

The ideal candidate anticipates needs, handles confidential information with discretion, and thrives in a fast-growing technology environment, partnering with executives and cross-functional teams.

Qualifications

• 5+ years as an Executive Assistant supporting C-level executives, preferably in high-growth tech or SaaS.
• Proven ability to manage calendars across multiple leaders and resolve conflicts.
• Experience coordinating domestic and international travel end-to-end.
• Strong written and verbal communication, with professional polish for external representation.
• Comfort with AI tools and automation to streamline day-to-day tasks.

Responsibilities

• Manage complex calendars across three executives, prioritizing meetings by business impact.
• Coordinate end-to-end domestic and international travel (flights, lodging, transport).
• Prepare agendas, briefing documents, and notes for leadership meetings and events.
• Act as gatekeeper between executives and internal/external stakeholders.
• Oversee day-to-day operations of the West Hollywood office and facilities.

Skills

Calendar management

Travel coordination

Executive communications

AI tools (Claude)

Multi-exec support

Discretion & judgment

Independent work

Tools

Google Workspace

Slack

Zoom

Expense & travel tools

Job description

About Pearl

Pearl is shaping the future of dentistry with a suite of AI solutions engineered to establish higher standards of quality and care for patients worldwide. Since 2019, our team has developed FDA-cleared computer vision capabilities for the interpretation of 2D and 3D dental imagery, industry-leading technology that clinicians, practice owners, labs, and insurers use to elevate the efficiency, accuracy, and consistency of dental care globally.

About Pearl

Pearl is shaping the future of dentistry with a suite of AI solutions engineered to establish higher standards of quality and care for patients worldwide. Since 2019, our team has developed FDA-cleared computer vision capabilities for the interpretation of 2D and 3D dental imagery, industry-leading technology that clinicians, practice owners, labs, and insurers use to elevate the efficiency, accuracy, and consistency of dental care globally.

The Role

We are seeking a proactive, detail-obsessed, and highly organized Executive Assistant to support Pearl's CEO, CTO, and COO. This role is the operational backbone of our executive team: you will own complex calendars, coordinate travel and events, prepare materials for board and leadership meetings, and keep three fast-moving executives focused on what matters most. You will also manage the day-to-day operations of our small West Hollywood office, keeping it running smoothly and welcoming for the team and visitors. The ideal candidate anticipates needs before they surface, handles sensitive information with absolute discretion, and thrives on bringing order to a dynamic, high-growth environment. This role requires exceptional judgment, ownership, and the ability to operate independently once expectations are clear.

Key Responsibilities

• Manage complex, ever-changing calendars across three executives, prioritizing meetings based on business impact and resolving conflicts proactively
• Coordinate domestic and international travel end to end, including flights, lodging, ground transportation, and detailed itineraries
• Prepare agendas, briefing documents, and follow-up notes for leadership meetings, customer visits, and industry events
• Serve as a gatekeeper and point of contact between executives and internal teams, customers, investors, and partners
• Plan and execute executive offsites, team events, and conference logistics
• Manage expense reports, invoices, and approvals for the executive team in a timely, accurate manner
• Draft, review, and polish executive communications, presentations, and correspondence
• Track action items and commitments across the executive team and follow up to ensure completion
• Handle confidential company, personnel, and financial information with complete discretion
• Manage day-to-day operations of our small West Hollywood office, including supplies, snacks, mail, vendors, and facilities requests
• Serve as the point of contact for building management and coordinate office access for employees and guests
• Greet and host visitors, and coordinate onsite meetings, lunches, and in-office events
• Identify and fix process gaps in how the executive office runs; own the fixes rather than waiting for direction
• Support special projects and cross-functional initiatives as assigned by the CEO, CTO, or COO

What You'll Need to Succeed

• 5+ years of experience as an Executive Assistant, with at least 5 years supporting C-level executives, ideally in a high-growth technology or SaaS environment
• Demonstrated fluency using AI assistants (e.g., Claude) to automate day-to-day tasks and set up recurring workflows
• Experience with office management or workplace operations a plus
• Proven ability to support multiple executives simultaneously and prioritize competing demands
• Exceptional written and verbal communication skills, with the polish to represent executives externally
• Advanced proficiency with Google Workspace, Slack, Zoom, and expense/travel tools; comfort learning new software quickly, including AI tools
• Impeccable attention to detail and follow-through
• High degree of discretion and sound judgment with confidential information
• Ability to work independently, anticipate needs, and flag issues before they become problems
• Calm, resourceful, and solutions-oriented under pressure in a fast-paced environment
• Based in the Los Angeles area, with the ability to work from our West Hollywood office 2-3 days per week

What we offer

• Competitive compensation and benefits
• Professional development and training opportunities
• Flexible, uncapped PTO
• Stock options
• Hybrid work model (2-3 days per week in our West Hollywood office)