Sierra

Sierra, co-founded by Bret Taylor and Clay Bavor, works on conversational AI and enterprise agents. Two questions recur: how agent work gets billed, and how engineers get hired.

On 10 December 2024, Elliot Greenwald tied Sierra's pricing to completed outcomes rather than seats or usage: a resolved support conversation, a saved cancellation, an upsell. "If the conversation is unresolved, in most cases, there's no charge", and escalations generally carry no billing. Greenwald names the conflict facing legacy CX vendors: the more effective their AI becomes, the fewer contact center seats their clients need.

In April 2026, Bret Taylor, then Vijay Iyengar, Arya Asemanfar and Angie Wang, described Sierra's rebuilt engineering interview. The onsite runs plan, build (two solo hours with the candidate's own AI tools), review. The coding phone screen became a system design interview, on the argument that vibe coding is easy while scalable production is not. A debugging interview is being piloted: the candidate reviews a colleague's draft PR by iterating with coding agents. Sierra recruits for strengths rather than the absence of weaknesses, and debriefs now ask where a person will excel.

Bain & Company's May 2026 brief on cross-system labor lists Sierra under autonomous customer issue resolution, alongside Glean, GitHub Copilot and Cursor. The pricing argument and the hiring redesign rest on one premise: the unit of value is a finished outcome rather than a seat or an hour.