Sierra

Enterprise AI Agents — Founded by Bret Taylor

The consensus on Sierra: in-person-first culture with elite founders and one of the fastest revenue ramps in enterprise SaaS history — strong equity at a $15B valuation, but expect a demanding pace.

San Francisco
Headquarters
~500
Employees
$150M+
ARR
~$15B
Valuation
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Culture Overview

What it's really like to work at Sierra

Sierra is building enterprise AI agents, founded in 2023 by Bret Taylor (ex-Salesforce co-CEO) and Clay Bavor (ex-Google VP). The company crossed $100M ARR in roughly seven quarters and reported $150M+ ARR in early 2026, on the back of a $950M Series E that valued Sierra at $15B. The culture is in-person-first, engineering-driven, and fast-moving, with elite founders who have proven track records in building world-class products.

Glassdoor Ratings

Sierra Glassdoor Ratings & Employee Reviews

4.0
Overall Glassdoor Score
Based on 13 reviews — limited volume
Culture & Values4.0
Work-Life Balance3.5
Compensation & Benefits4.2
Career Opportunities3.8
Senior Management4.0
Overall Rating4.0
Employee Review Themes

Working at Sierra: Pros & Cons

What employees love

  • Founded by Bret Taylor (ex-Salesforce co-CEO) — elite leadership
  • Crossed $100M ARR in ~7 quarters and continued scaling to $150M+ ARR in early 2026
  • Elite founders with proven track records
  • Strong equity at $15B valuation (May 2026 Series E)

What could be better

  • Primarily in-person culture — remote not the default
  • Rapidly scaling org means roles evolving fast
  • In-person-first culture
  • Competitive intensity may not suit everyone
Engineering Culture

How the engineering team works

Tech Stack

PythonTypeScriptAI/ML

Product

Enterprise conversational AI agents that handle customer interactions across industries. Trusted by leading brands for customer experience automation.

AI & ML

Building conversational AI agents powered by large language models, with enterprise-grade reliability and safety. Learn more →

Team Structure

~500 employees with engineering-driven culture. In-person collaboration in San Francisco. Fast-moving teams with strong equity incentives and learning opportunities.

Open Positions

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