Executive Assistant, Sales & Agent Development

Sierra•New York, NY

2d•$130,000 - $170,000•Onsite

About The Position

Sierra is hiring an Executive Assistant to provide comprehensive, high-touch support to several customer-facing leaders across its Sales and Agent Development organization. The role manages complex calendars, meetings, travel, expenses, customer engagements, and executive briefings while balancing internal priorities and customer commitments. It also partners with leaders and teams to prepare meetings, coordinate follow-ups, support recruiting and team operations, and plan events such as off-sites, hackathons, and team travel. The Executive Assistant collaborates with other Executive Assistants and cross-functional partners, builds relationships across product, engineering, and operations, and establishes administrative systems for a rapidly scaling organization. The role requires independent judgment, discretion with sensitive information, and the ability to work on-site in San Francisco four days per week. Sierra is a customer-facing AI platform company with a primarily in-person culture and offices across North America, Europe, and Asia. Its stated values are Trust, Customer Obsession, Craftsmanship, Intensity, and Family.

Requirements

At least 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 professionalism, responsiveness, and sound judgment when interacting with customers and external stakeholders.
Exceptional attention to detail and a proactive mindset.
Excellent organizational and time-management skills, including the ability to shift priorities quickly while remaining accurate and proactive.
Ability to operate independently, anticipate needs, and make sound judgment calls on behalf of leadership.
Strong relationship-building skills and ability to partner effectively with cross-functional teams and external stakeholders.
High integrity and discretion when handling confidential or sensitive information.
Advanced proficiency with Google Workspace and Slack, and ability to learn new tools quickly.
Willingness and ability to work on-site in San Francisco four days per week.

Nice To Haves

Experience in a fast-growing, in-person start-up environment.
Experience working with C-suite executives.
Experience working within a dual, floating, or team-based Executive Assistant structure.
Experience managing complex travel, executive events, and high-touch on-site logistics.

Responsibilities

Provide comprehensive, high-touch executive support to several customer-facing leaders in Sales and Agent Development.
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 they are prepared and executed thoughtfully.
Anticipate scheduling conflicts, changing needs, and competing priorities; resolve issues independently and keep commitments moving forward.
Coordinate domestic and international travel, including itineraries, accommodations, agendas, logistics, and preparation.
Prepare meeting materials and agendas, track action items, and coordinate follow-ups with leaders and their teams.
Collaborate with Executive Assistants and cross-functional partners to coordinate priorities and organizational alignment.
Build working relationships with teams across product, engineering, operations, and other functions.
Support recruiting coordination, team operations, and other administrative needs.
Plan and execute team events, including leadership meetings, off-sites, hackathons, and team travel.
Establish and continuously improve administrative systems and processes for multiple leaders and a rapidly scaling organization.
Handle sensitive information, technical roadmaps, personnel matters, and strategic communications with confidentiality and discretion.

Benefits

Flexible (unlimited) paid time off.
Medical, dental, and vision benefits for the employee and family.
Life insurance and disability benefits.
Retirement plan dependent on country of employment.
Parental leave.
Fertility and family building benefits through Carrot.
Lunch, snacks, and coffee.
Discretionary benefit stipend.
Free alphorn lessons.
Eligible full-time employees can participate in Sierra's equity plans, subject to applicable plan terms and policies.