OnsiteBret Taylor's enterprise AI company just raised $950M. They have 129 roles to fill.
The opportunity
- ✓129 open roles — #2 on Employbl by open headcount
- ✓$950M Series E closed May 2026
- ✓Founded 2023 by Bret Taylor and Clay Bavor
- ✓Enterprise AI agents deployed at WeightWatchers, SiriusXM, Sonos
- ✓Total funding exceeds $1.5B — one of the most-funded AI startups of the cycle
Currently hiring
Software engineers (AI platform, infrastructure, integrations)ML engineers and researchersEnterprise account executivesSolutions engineersCustomer success managersProduct managers
129 open roles as of June 2026 — #2 on Employbl by open headcount. The hiring push began immediately after the May 2026 Series E close.
Common misconception
Q: Who are the founders?
A: Bret Taylor (co-CEO of Salesforce 2021–2023, Twitter board chairman, co-creator of Google Maps and FriendFeed) and Clay Bavor (built Google VR, led Google Labs). The founding team is as credentialed as any in enterprise software history.
Q: Who are Sierra's customers?
A: Enterprise companies using Sierra agents for customer service operations. Published customers include WeightWatchers, SiriusXM, and Sonos. Sierra targets large organizations with high-volume customer interaction workflows.
Q: What's the engineering culture like?
A: Small teams, high autonomy, extremely high bar. Sierra is still small relative to its valuation — meaning early employees have significant ownership of product direction. They hire for people who operate effectively in ambiguity and build from first principles.
Q: What roles are they hiring for?
A: 129 open roles across engineering, product, go-to-market, and operations. Software engineers (AI/ML, platform, infrastructure), enterprise sales, solutions engineers, and customer success roles dominate current openings.
Q: What does the equity situation look like?
A: Sierra raised its Series E at a multi-billion dollar valuation in May 2026. Pre-IPO equity at this stage carries meaningful upside for strong performers joining now.
Tech stack
PythonTypeScriptLLMs (frontier + proprietary models)Cloud infrastructure (AWS/GCP)Agentic orchestration frameworks
Customers
WeightWatchersSiriusXMSonosEnterprise companies across retail, media, and consumer services
Funding
$950M Series E closed May 2026, bringing total funding to over $1.5B. The round was led by Sequoia and valued Sierra at over $4B. Capital is being deployed into product development, enterprise sales expansion, and international growth.
Backed by
Sequoia CapitalBenchmarkThrive CapitalGreenoaks Capital
Perks
Competitive salary and equity at pre-IPO valuationComprehensive health, dental, and vision insuranceCentral San Francisco officeCatered meals401kGenerous PTOParental leave
Culture
High-performance culture shaped by founders who built at the highest levels of Salesforce and Google. Small team size means high individual ownership. Bias toward action, technical depth, and building enterprise software that actually works in production. San Francisco in-office culture with a strong emphasis on in-person collaboration.
