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Salary
$230k – $390k per year
Location
In office (San Francisco)
Employment
Full-Time
Overview
Company
Impact
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Sierra, formerly known as Sierra Trading Post, is a major American off-price retailer operated by The TJX Companies. The company offers a wide selection of discounted activewear, outdoor recreation gear, footwear, apparel, and home goods from top name brands.

About us

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 do

The Payments Infrastructure team builds the trust boundary between a live conversation and the rest of Sierra: sensitive data enters through a customer's voice or chat, leaves as a token, and the agent never sees the plaintext in between. Doing this well means weaving four hard domains together at once: LLMs, payments, infrastructure, and voice. Done right, it unlocks seamless, compliant payments for every Sierra agent and the people who use them. It's already one of the highest-containment features Sierra ships: when an agent can take a payment, the conversation keeps going instead of transferring to a person, so the agent resolves everything around it too. The platform is PCI DSS Level 1, on Visa's Global Registry, and carries cardholder data across millions of payment lifecycle events for enterprise customers.

  • Design the secure-capture protocol every channel sits behind, so the payment feels like one continuous conversation to the person on the other end, while telephony providers, contact-center platforms, embedded chat, and Sierra's own voice stack all present a single event lifecycle to agent code, no matter how different each customer's stack is.

  • Build and extend the tokenization platform: per-token envelope encryption with a unique data key per token, so a single compromised decrypt exposes one token at most.

  • Own the security perimeter around the cardholder-data environment, so what each system can reach is enforced by infrastructure rather than convention, and auditable by design.

  • Build deterministic, auditable detection in the agent's hot path that catches the cardholder data general-purpose models miss, and help design the purpose-built detection model that comes next. No LLM, including any we build ourselves, ever sees plaintext cardholder data.

  • Make payments something other engineers can use without becoming compliance experts: drive the platform toward processor-agnostic charging, self-serve onboarding, and single-tenant deployments, so a team can add payments to an agent without a payments infrastructure engineer in the loop.

  • Set technical direction across the team's hardest problems, get the abstractions right so we solve each one once rather than per customer, and raise the bar for the engineers around you.

What you'll bring

  • 7+ years building backend, platform, or infrastructure systems, with a track record of shipping and operating high-reliability services in production at a strong engineering organization.

  • A deep security instinct. You design as though every component will eventually be compromised, and you reason naturally about blast radius, least privilege, and making bad states impossible rather than reacting to them.

  • Fluency in a systems language (we use Go) and comfort owning critical distributed systems end to end, from design through production and on-call.

  • A record of setting technical direction on ambiguous, high-stakes problems, and getting the abstractions right so they hold up across teams and customers.

  • A generalist's instinct. You build clean abstractions and protocols over messy, inconsistent external systems, and you're never satisfied solving a problem once per customer.

  • Degree in Computer Science or a related field, or equivalent professional experience.

Even better…

  • Experience in a regulated or sensitive-data domain such as payments, PCI, tokenization, key management, or healthcare and PHI.

  • Depth in one of our core areas: applied cryptography and key management; voice, telephony, or real-time media pipelines; or cloud security and network isolation.

  • Experience building platforms other engineering teams build on, such as internal protocols, SDKs, and self-serve developer services.

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 are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.

What we offer

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 us

We'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.

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