Executive Assistant, Sales & Agent Development

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ABOUT US Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia. We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do. Sierra was co-founded by Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/ who first met while working together at Google over 20 years ago. Bret currently serves as Chairman of the Board of Open AI. Previously, he was co-CEO of Salesforce and CTO of Facebook. Clay spent 18 years at Google, where he most recently led Google Labs. WHAT YOU'LL DO - 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. WHAT YOU'LL BRING - 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

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