Strategic Executive Assistant for Sales & Agent Development

Sierra; New York (NY); On-site; USD 90,000 - 150,000; Full time

Benefits offered by this job

Unlimited PTO

Medical, dental, vision benefits

Life insurance and disability benefits

Retirement plan (country dependent)

Parental leave

Equity plans subject to policy

Job summary

Sierra is seeking an experienced Executive Assistant to support multiple senior leaders at a fast-growing, in-person company. The role requires coordinating complex calendars, travel, and meetings across teams, ensuring flawless executive operations and confidential handling of sensitive information.

You will partner with product, engineering, and operations, facilitating efficient meetings, materials, and follow-ups while maintaining high standards of professionalism and responsiveness.

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.
• Exceptional attention to detail and a proactive mindset, with a commitment to creating polished and seamless experiences for leaders, customers, and internal partners.
• Excellent organizational and time-management skills, with the ability to shift priorities quickly while remaining accurate and proactive.
• Proven ability to operate independently, anticipate needs, and make sound judgment calls on behalf of leadership.
• Strong relationship-building skills and the 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, 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

Google Workspace

Slack

On-site coordination

Tools

Google Workspace

Slack

Job description

Sierra is seeking an experienced Executive Assistant to support multiple senior leaders at a fast-growing, in-person company. The role requires coordinating complex calendars, travel, and meetings across teams, ensuring flawless executive operations and confidential handling of sensitive information.

You will partner with product, engineering, and operations, facilitating efficient meetings, materials, and follow-ups while maintaining high standards of professionalism and responsiveness.