Sierra
Forward Deployed Infrastructure Engineer
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About Sierra
At Sierra, we’re creating a platform to help businesses build better, more human customer experiences with AI. We are primarily an in-person company based in San Francisco, with growing offices in Atlanta, New York, London, Paris, Madrid, Munich, Singapore, Tokyo, and Sydney.
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 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.
About the Role
As a Forward Deployed Infrastructure Engineer at Sierra—and a founding member of this function—you will:
- Own the end-to-end lifecycle of customer deployments, while helping define how Sierra’s AI platform is deployed and operated across enterprise environments.
- Work directly with enterprise customers to architect, deploy, upgrade, and manage Sierra’s AI platform infrastructure—ensuring every deployment meets their security, compliance, and operational requirements.
- Establish standards, tooling, and processes that make deployments scalable and repeatable, and partner cross-functionally with Engineering, Product, Sales, and Customer Success.
- Define how Sierra scales some of its most complex customer engagements.
Responsibilities
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Owning Deployment Architecture
- Design and implement deployment strategies across customer environments, including VPC configuration, permissioning, networking, and infrastructure provisioning.
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Managing Infrastructure Lifecycle
- Execute initial deployments, ongoing upgrades, scaling, and incident support for some of Sierra’s most critical customers.
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Developing Deployment Standards
- Develop and maintain deployment runbooks, upgrade procedures, and automation tooling to ensure operations are repeatable and reliable.
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Collaborating Across Functions
- Partner with engineering teams to ensure Sierra’s platform is deployable and operable across diverse customer requirements.
- Work with customers' platform engineering, security, and DevOps teams to address infrastructure constraints and compliance requirements.
- Collaborate with Sales and Customer Success to scope infrastructure requirements during pre-sales and onboarding, translating customer needs into concrete deployment plans.
Requirements
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Experience:
- 4+ years in infrastructure, DevOps, platform engineering, or solutions architecture roles—with significant time spent on customer-facing deployment work.
- Deep experience with AWS services, Terraform, container orchestration, and cloud networking (VPCs, IAM, DNS, load balancing).
- Track record of managing deployments in customer-owned cloud environments, including navigating security reviews, compliance requirements, and change management processes.
- Ability to navigate ambiguity with enterprise stakeholders (from platform engineers to CISOs) and turn infrastructure conversations into actionable deployment plans.
- Strong operational instincts: thoughtful consideration of upgrades, rollbacks, monitoring, and failure modes from the beginning—not an afterthought.
- Comfortable working in a fast-moving environment, collaborating with engineering, product, and go-to-market teams.
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Education:
- Degree in Computer Science or a related field, or equivalent professional experience.
Nice-to-Haves
- Hands-on experience with Go services, GraphQL APIs, or LLM infrastructure in production environments.
- Past experience at an early-stage company where you built deployment operations, playbooks, and tooling.
- Familiarity with observability and incident management in distributed systems (Prometheus, Grafana, Datadog, or similar).
- Experience with CI/CD pipeline design, deployment automation, or infrastructure self-service tooling for enterprise customers.
Our Values
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Trust
- We build trust with our customers with 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 supporting one another, professionally and personally, creating an environment that enables all of us to do our best work.
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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.
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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 time to fix it. We are proud of the products we produce.
- We continuously self-reflect to continuously self-improve.
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Intensity
- We don’t have the luxury of patience. We play to win, caring deeply about our product being the best.
- When it isn’t, we fix it. When we fail, we talk about it openly and without blame, ensuring we succeed the next time.
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Family
- We know that balance and intensity are compatible and model this in our actions and processes.
- We are the best technology company for parents, supporting and respecting each other while celebrating our personal and professional achievements.
Benefits
We prioritise benefits that align with our values, including:
- 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
- Free lunch, snacks, and coffee to keep you energised
- Discretionary benefit stipend—flexibility to spend where it matters most
- Free alphorn lessons
These benefits may vary by region and are subject to change in alignment with compensation and benefit plans. Eligible full-time employees can also participate in Sierra’s equity plans according to applicable terms and policies.
Be You, With Us
We’re working to bring AI’s transformative power to every organisation in the world. To do so, we believe our diversity must reflect the diversity of our customers. We encourage representation of different skills and experiences, and we evaluate all applicants fairly, without regard to race, colour, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class.
Apply even if your experience doesn’t precisely match the job description—we’re here to build together.
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