Executive Assistant, Sales & Agent Development

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. Our co-founders are Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace. 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 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. EVEN BETTER... - 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. OUR VALUES - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work. - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it. - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve. - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time. - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We a