Strategic Executive Assistant to Sales Leaders (On-Site SF)

sierra.ai; New York (NY); On-site; USD 90,000 - 130,000; Full time

Benefits offered by this job

Flexible PTO

Medical, dental, and vision benefits

Life insurance

Retirement plan

Parental leave

Job summary

Sierra is the leading platform for customer-facing AI agents, with offices in San Francisco and across North America. This Executive Assistant role supports multiple senior leaders, managing calendars, travel, and communications to ensure seamless operations.

You will partner with cross-functional teams, coordinate meetings and briefings, and handle confidential information with discretion in a fast-paced, in-person environment.

Qualifications

• 5+ years of Executive Assistant or similar strategic support experience.
• Demonstrated ability to support multiple customer-facing senior leaders simultaneously while adapting to different communication styles, priorities, and working preferences.
• Experience supporting technical, product, or engineering leaders in a fast-paced environment.
• Strong customer orientation and the ability to interact with customers and external stakeholders with professionalism, responsiveness, and sound judgment.
• Advanced proficiency with Google Workspace and Slack, along with the ability to learn new tools quickly.
• Willingness and ability to work on-site in San Francisco four days per week.

Responsibilities

• Serve as a trusted partner to several customer-facing leaders across Sierra’s Sales and Agent Development organization, providing comprehensive, high-touch executive support.
• Proactively manage complex calendars, meetings, travel, and expenses across multiple leaders, balancing internal priorities with customer commitments.
• Coordinate customer meetings, executive briefings, and external engagements, ensuring each interaction is thoughtfully prepared and executed.
• Anticipate scheduling conflicts, changing needs, and competing priorities, resolving issues independently and keeping commitments moving forward.
• Coordinate domestic and international travel, with careful attention to itineraries, accommodations, agendas, logistics, and preparation.
• Partner with leaders and their teams to make meetings effective by preparing materials, developing agendas, tracking action items, and coordinating follow-ups.
• Collaborate closely with Executive Assistants and cross-functional partners across Sierra to coordinate priorities and ensure alignment across the organization.
• Build strong working relationships with teams across product, engineering, operations, and other functions.
• Support recruiting coordination, team operations, and other administrative needs as the organization grows.
• Plan and execute team events, including leadership meetings, off-sites, hackathons, and team travel.
• Establish and continuously improve administrative systems and processes that support multiple leaders and a rapidly scaling organization.
• Handle sensitive information, technical roadmaps, personnel matters, and strategic communications with confidentiality and discretion.

Skills

Executive support

Calendar management

Travel coordination

Stakeholder management

Cross-functional collaboration

Attention to detail

Time management

Independent decision making

Relationship building

Discretion with confidential info

Google Workspace

Slack

On-site coordination SF

Tools

Google Workspace

Slack

Job description

Sierra is the leading platform for customer-facing AI agents, with offices in San Francisco and across North America. This Executive Assistant role supports multiple senior leaders, managing calendars, travel, and communications to ensure seamless operations.

You will partner with cross-functional teams, coordinate meetings and briefings, and handle confidential information with discretion in a fast-paced, in-person environment.