Sierra
Conversational AI & Agentic Platforms / Enterprise Generative AI SaaS / Customer Experience & Automation Tools / Developer-First AI Infrastructure San Francisco, California / United States / Remote
Sponsored
About Sierra
Sierra (operating under sierra.ai, legally Sierra Technologies, Inc.) is the premier, enterprise-grade autonomous AI agent platform, conversational intelligence pioneer, and generative AI orchestration powerhouse engineered to act as the definitive, brand-aligned customer experience and transaction resolution layer for global enterprises. Co-founded in 2023 by tech luminaries Bret Taylor (former co-CEO of Salesforce, CTO of Facebook, and Chairman of the Board at OpenAI) and Clay Bavor (former Google Vice President leading Google Workspace and AR/VR initiatives), the company completely eliminates the severe limitations of traditional conversational bots—where legacy chat setups rely on static decision-trees, struggle with open-ended natural language, and fail to carry out real, multi-step back-office transactions—by deploying a sophisticated, enterprise-ready Agent OS. Moving far beyond passive FAQ responders or basic keyword matching widgets, Sierra natively unifies deep, multi-turn reasoning engines, strict goal-oriented behavior scripting, real-time enterprise system-of-record integrations (such as Salesforce, Shopify, and Zendesk), and active policy governance modules into a high-availability, compliance-first platform. Operating with massive commercial velocity, its brand-native AI agents are trusted by household names like Sonos, SiriusXM, WeightWatchers, ADT, Casper, and Chubbies to handle complex customer support, billing inquiries, and service modifications autonomously. Highlighting its category-defining momentum and meteoric growth trajectory, the company closed a monumental $950 million Series E financing round in May 2026 led by Tiger Global and Google's GV, with heavy-tier participation from Sequoia Capital, Benchmark, Thrive Capital, and Greenoaks Capital, catapulting its market valuation to an astronomical $15.8 billion. Under the hood, its technology core utilizes its proprietary \"Constellation\" architecture—a multi-layered model structure that leverages a primary LLM (utilizing models from OpenAI, Anthropic, and Meta) paired with secondary supervisor models to monitor response appropriateness—designed to execute complex API transactions with millisecond-level orchestration latency. What sets Sierra apart is its uncompromising dedication to replacing fragile, script-bound chatbots with absolute conversational predictability, dynamic transaction resolution, and rigorous data compliance (SOC 2, HIPAA, GDPR, and CCPA); by bridging the gap between performance-intensive frontier model intelligence and high-level enterprise business logic, the company remains a definitive cornerstone of modern algorithmic customer operations and global generative AI transformation.

Inside look: Remote culture and values at Sierra
Founded In2023
Company Size501 - 1000 Employees
IndustryConversational AI & Agentic Platforms / Enterprise Generative AI SaaS / Customer Experience & Automation Tools / Developer-First AI Infrastructure
Open Positions11 Roles
Shopify Growth Developer (CRO), DTC Wellness Brand
Remote (Brazil)
$50k – $100k USD per year, DOE
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Backend Engineer, AI Integrations
Remote (Brazil)
$60k - $100k annually
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Director of Public Sector Sales
Remote (United States(San Francisco, New York City), Canada)
Salary Not Disclosed
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Lead AI Engineer
Remote (Brazil)
$70k – $120k USD
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GTM Technical Expert – Public Sector (Federal/State) at Sierra
Remote (United States(San Francisco, New York City), Canada, Gabon)
Salary Not Disclosed
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Enterprise Sales Leader (Regional)
Remote (United States(San Francisco, New York City), Canada, Gabon)
Salary Not Disclosed
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Enterprise Account Executive
Remote (Canada)
Salary Not Disclosed
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Enterprise Sales Lead (AI Platform)
Remote (United States(San Francisco, New York City), Canada, Gabon)
Salary Not Disclosed
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Enterprise Sales Representative
Remote (United States(San Francisco, New York City), Canada, Gabon)
Salary Not Disclosed
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Enterprise Sales Representative
Remote (Canada)
Salary Not Disclosed
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Senior Software Engineer (AI & Robotics)
Remote (Brazil)
$100k – $150k base, plus equity
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Benefits and perks at Sierra
Learn about the 4 benefits and perks Sierra offers its remote employees.
🏥
Health & Medical
Comprehensive medical, dental, and vision coverage for you and your dependents.
🏡
Flexible Working
Work from anywhere with flexible hours that fit your personal lifestyle.
💻
Home Office Setup
Generous stipend to set up a comfortable and productive remote workspace.
🧘
Wellness Perks
Allowances for gym memberships, mental health apps, and overall wellbeing.
Salary ranges at Sierra
Estimated compensation ranges based on 4 active job postings.
Highest Compensation
$150k/yr
Data Availability
36%
of open roles have disclosed salaries.
Salary ranges by position
Min Max
$50k – $100k USD per year, DOE
$60k - $100k annually
$70k – $120k USD
$100k – $150k base, plus equity
$0$150k+