At Sierra, we’re building a platform to enable every company in the world to build better, more human customer experiences with AI. We partner with industry leaders such as SoftBank, Uber, Rivian, CLEAR, and Sutter Health. 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 Family. 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 and Clay Bavor. 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 doAs an Executive Assistant supporting the Office of the Co-Founders at Sierra, you will provide a wide range of strategic and administrative support to our Co-Founders and their teams.
Play a pivotal, high-trust role in a dynamic, fast-paced environment. You’ll partner closely with the existing executive support team to execute complex logistics, travel, meetings, events, and special projects with precision and foresight.
Act as a second assistant to our Co-Founders, coordinating complex travel, running logistics for all onsite meetings, helping the team with projects (large trip planning, events, etc) and generally be ready and able to jump in when extra support is needed.
Anticipate needs, identify potential issues, and proactively develop solutions that keep priorities and commitments moving forward.
Serve as a trusted liaison to internal teams, vendors, and external partners, building strong relationships while safeguarding the priorities of the Office of the Co-Founders.
Plan and execute leadership travel, team off-sites, executive dinners, on-site meetings, and other internal or personal events as needed.
Take ownership of evolving requests and projects, remaining flexible and ready to provide additional support wherever it is most needed.
Handle sensitive information and materials with the utmost confidentiality, discretion, and sound judgment.
3+ years of experience in executive support or a similar high-level administrative role.
Willingness and ability to work on-site in San Francisco up to five days per week, including consistent presence when the co-founders are on-site.
Exceptional attention to detail and an anticipatory, white-glove service mindset, with the ability to operate independently and deliver polished, seamless support with limited direction.
Exceptional organizational and time-management skills, with the ability to manage competing priorities accurately in a fast-paced environment.
Proven ability to partner effectively with senior executives, cross-functional teams, vendors, and external stakeholders.
Advanced proficiency with Google Workspace and Slack, along with the ability to learn new tools quickly.
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.
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 are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.
We want our benefits to reflect our values and offer the following to full-time employees:
Flexible (unlimited) paid time off
Medical, dental, and vision benefits for you and your family
Life insurance and disability benefits
Retirement plan dependent on country of employment
Parental leave
Fertility and family building benefits through Carrot
Lunch, as well as delicious snacks and coffee to keep you energized
Discretionary benefit stipend giving people the ability to spend where it matters most
Free alphorn lessons
These benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.
Be you, with usWe're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class.
Skills Required
- 7+ years of Executive Assistant or similar experience
- Ability to build relationships and partner effectively with cross-functional teams and external partners
- Excellent time management skills and ability to shift tasks and priorities quickly
- Ability to anticipate executive needs proactively
- Ability to organize, analyze, and prioritize executive workflows, including interpreting data
- Ability and willingness to work in the San Francisco office four days per week
- Willingness and ability to travel as needed, estimated at twice per quarter
- Experience in a fast-growing, in-person startup environment
- Advanced proficiency with Google Suite and Slack
Sierra Compensation & Benefits Highlights
The following summarizes recurring compensation and benefits themes identified from responses generated by popular LLMs to common candidate questions about Sierra and has not been reviewed or approved by Sierra.
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Healthcare Strength — Health coverage is described as top-tier medical, dental, and vision, alongside life insurance. These protections are highlighted consistently in company materials.
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Parental & Family Support — Parental leave is described as generous, with fertility and family-building benefits noted (e.g., via Carrot). These offerings emphasize support for families across life stages.
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Flexible Benefits — An annual discretionary stipend can be used for personal needs like equipment, childcare, or a phone plan. Food and onsite comfort perks such as lunch, snacks, and coffee are also included.
Sierra Insights
What We Do
Sierra is the conversational AI platform for businesses. We help companies elevate their customer experience with AI








