Sierra

Software Engineer, Agent - Retail

Sierra
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3 hours ago
Toronto, Canada +3 moreSenior
H1B sponsor

Responsibilities

  • Design and deliver performant, reliable, intuitive AI agents for production retail environments.
  • Own the full Agent Development Life Cycle from pilot and deployment through continuous iteration.
  • Partner directly with enterprise and startup customers to understand business challenges and build AI-agent solutions.
  • Prototype tools and features, surface customer needs, and collaborate with research, product, and platform teams to evolve Sierra’s platform.
  • Build commerce capabilities spanning order management, fulfillment, returns, warranties, product discovery, checkout, payment, and order placement.
  • Develop systems that support high-volume, global traffic across web, app, phone, and in-store channels.

Requirements

  • Experience building and scaling end-to-end production systems.
  • Strong technical problem-solving skills in fast-changing and ambiguous environments.
  • Builder and tinkerer mindset with high agency and the ability to ship creative solutions.
  • Comfort working directly with customers to understand needs and solve real-world problems.
  • Excellent communication skills across technical and non-technical audiences.
  • Excitement about retail and helping major brands build customer loyalty.
  • Preferred: experience building or deploying AI/LLM systems in production.
  • Preferred: founder or founding-engineer experience.
  • Preferred: familiarity with evaluation frameworks, agent tooling, RAG pipelines, and prompt engineering.
  • Preferred: experience with React, TypeScript, and/or Go.
  • Preferred: experience interfacing with customers or leading technical projects with external stakeholders.

Benefits

  • Flexible unlimited paid time off.
  • Medical, dental, and vision benefits for employees and families.
  • Life insurance and disability benefits.
  • Retirement plan dependent on country of employment.
  • Parental leave.
  • Fertility and family-building benefits through Carrot.
  • Lunch, snacks, and coffee provided.
  • Discretionary benefit stipend.
  • Free alphorn lessons.
  • Equity plan participation for eligible full-time employees.
  • Primarily in-person work based in San Francisco, with offices across North America, Europe, and Asia.
Sierra

About Sierra

1,001-5,000 employees

Sierra builds an enterprise conversational AI platform that powers customer service and other customer-facing interactions for large organizations. The company sells SaaS and deployed solutions that integrate with enterprise systems and meet security and compliance requirements. Headquartered in San Francisco with offices across North America, Europe, and Asia-Pacific, Sierra was co-founded by Bret Taylor and Clay Bavor, longtime leaders at Salesforce, Facebook, and Google.

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