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AI & Machine Learning

Sierra is hiring. 188 roles are open right now.

Browse the openings below to see requirements, locations, and pay where available. Scoutify can fill in and send your application to the ones that match your search.

Posted (90d)114

INTERVIEW PREP

17 interview questions for Sierra (17 from real candidates)

See 17 interview questions

[01] HIRING NOW

See Sierra's current openings.

We update these listings as we find new roles and learn that others have closed.

Open roles

188

Posted (90d)

114

Posted range

—

Roles with the most current openings

Sales Engineer
36 roles
Sales
35 roles
Software Engineer
32 roles
Machine Learning Engineer
27 roles
AI / LLM Engineer
25 roles

[02] OPEN ROLES

Apply to Sierra now.

Live roles pulled from Sierra's career page. Open one to see the full description, location, and pay, then let Scoutify apply for you, or apply on Sierra's site yourself.

Location

Type

The 20 most recent roles out of 188 open roles

Let Scoutify apply to Sierra for you.

Applying by hand takes about 10 minutes per role. Scoutify fills in and sends the application for you when a role matches your search.

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[03] VISA SPONSORSHIP

Hiring international candidates.

Sierra has a documented USCIS H-1B petition history.

Sponsors H1B · USCIS-confirmed petitioner

Source: USCIS H-1B Employer Data Hub. Classifications: yes (5+ approvals), conditional (1-4), no (0).

[04] WHERE THEY'RE HIRING

Where Sierra is hiring.

These are the cities named in current job listings. A role can appear in more than one city. Remote roles may also appear in these cities and can have location requirements.

Top cities by open roles

San Francisco, California
83 roles
London, England, GB
16 roles
Toronto, Ontario, CA
14 roles
Singapore, SG
9 roles
New York City, New York
6 roles
Sydney, New South Wales, AU
3 roles
Madrid, Madrid, ES
2 roles
Tokyo, Tokyo, JP
2 roles

Remote: 23 positions

+2 more locations

[05] OFFICES

Where Sierra works.

Sierra office locations

© Mapbox © OpenStreetMap

We've mapped a Sierra office at 1090 Don Mills Road Suite 300, Toronto, ON M3C 3R6, so you know where you'd report before you apply.

Office data © OpenStreetMap contributors

[06] LAYOFF HISTORY

What past rounds looked like.

Sierra has had 1 reported layoff round on public record since 2020. We list these because candidates routinely tell us they wish they had known before applying. Context, not a verdict.

Reported rounds

1

Headcount cut

115

Most recent

Nov 16, 2023

115 roles

Source

Source: Layoffs.fyi, public record

[07] IN THE NEWS

Sierra in the headlines.

Recent press coverage, pulled from Google News. Worth a scan before an interview or a cold email: funding rounds, launches, and leadership changes are the fastest way to sound current.

Conserving Sierra Leone’s western chimpanzees: Interview with Tacugama’s Willie Tucker - news - Mongabay

news - Mongabay
3 months ago

Sierra Club Reaches Settlement with Three Santa Barbara Companies over Harmful Runoff to East Beach

The Santa Barbara Independent
3 months ago

Source: Google News. Last 12 months.

[08] FROM THE POSTINGS

What the job postings tell us.

These details come from the linked postings. Benefits and working arrangements can differ by role and location.

Eligible full-time employees can participate in Sierra's equity plans, subject to the terms of the applicable plans and policies.

Source posting

Sierra encourages candidates to apply even if their experience does not precisely match the job description.

Source posting

Sierra's Enterprise Account Executive posting lists building sales teams and sales motions from scratch as a plus.

Source posting

Sources reviewed 2026-10-19.

[09] ABOUT

What Sierra does.

Sierra is creating a platform to help businesses build better, more human customer experiences with AI. It was co-founded by Bret Taylor and Clay Bavor.

[11] INTERVIEW PREP

Going through their loop?

Review the skills in Sierra's job descriptions, practice relevant exercises, and explore any available candidate-reported questions.

[12] HOW TO APPLY

Your resume lands in Ashby.

Sierra uses Ashby for applications. Follow the job link to complete the employer’s form and review its requirements.

Scoutify checks Sierra's career page for new listings.

Ashby is one of the career sites where Scoutify's AI auto apply works, so Sniper can submit your application to a matching Sierra role minutes after it posts. Sniper sends one application per posting, and the employer's confirmation email for most applications lands in Scoutify Mail.

ATS identified from the application URLs on Sierra's recent postings

[15] FAQ

Questions people ask about Sierra.

Not covered here? Email support@scoutify.com.

Is Sierra hiring?

Scoutify currently lists 188 open roles at Sierra. Follow the job links to check requirements and apply on the employer's career site.

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