Staff Software Engineer, AI Platform

Sentry; San Francisco (CA); On-site; USD 240,000 - 400,000; Full time

Benefits offered by this job

Commuter Stipend

Professional Development

Flexible PTO

Charitable Matching

Yoga breaks

Company match program

Job summary

Sentry is seeking a Staff engineer to evolve its AI debugger, Seer, and to decide how AI systems should grow as models evolve. You will lead end-to-end AI initiatives, work with developers and product teams, and deploy in production while continuously debugging and improving performance.

You will shape how agents obtain context, use tools, and determine completion, building evaluation frameworks to validate improvements fast and cost-effective.

Qualifications

• Shipped an LLM-backed system and can explain what broke.
• Strong opinions on agent design and have changed at least one in the last year.
• Trained or fine-tuned models when appropriate and know when not to.
• Proficient in production Python.
• Led work across multiple engineers and teams with design docs that are read.

Responsibilities

• Build state-of-the-art agentic AI systems to triage, debug, and solve real production issues.
• Set technical direction for how agents get context, use tools, and decide when they're done.
• Build evals to measure model/prompts impact quickly for adoption.
• Decide when to use frontier vs smaller/trained models as cost/capability shift.
• Leverage Sentry’s dataset of errors, spans, and profiles.
• Own major AI initiatives end to end with developers and product teams.

Skills

LLM-backed systems

Agent design

Production Python

Cross-team leadership

Technical documentation

Job description

Software runs the world and the pace is faster than ever. Sentry helps developers fix errors and performance issues before users notice, so teams can spend less time firefighting and more time building.

Trusted by 200,000+ organizations, Sentry is today’s application monitoring standard and our team is building its AI-native future.

About the role

Sentry already sees the moment software breaks: the error, the trace, the replay, the commit that caused it. Seer, our AI debugger, uses all of that to figure out what went wrong and how to fix it. We're looking for a Staff engineer to help decide how that system should evolve as models improve every few months. Some of what we build today will be obsolete by next spring. Part of the job is knowing which parts, and building the rest to last.

In this role you will

Build state-of-the-art agentic AI systems to triage, debug, and solve real production issues

Set technical direction for how our agents get context, use tools, and decide when they're done

Build the evals that tell us whether a new model or prompt actually helped, fast enough that people use them

Decide when to use a frontier model, a smaller one, or one we trained, and revisit that as cost and capability shift

Leverage Sentry’s novel (and massive) dataset of errors, spans, and profiles

Own major AI initiatives end to end, alongside the developers and product teams shipping them

Run what you ship in production and debug it with Sentry

You’ll love this job if you

Are driven by impact and enjoy working on high-stakes, high-visibility projects

Enjoy building things. You will have the opportunity to join the AI/ML team as one of its foundational members

Thrive in cross-functional teams and enjoy building features alongside developers and product teams

Qualifications

You've shipped an LLM-backed system people depended on, and can tell us what broke

You have strong opinions on agent design and have changed at least one in the last year

You've trained or fine-tuned models when it was the right call, and you know when it isn't

You write solid production Python

You've owned a system or component and led work across multiple engineers and teams, with a design doc people actually read

You write clear technical documentation, mentor other engineers, and present to technical audiences

The base salary range (or hourly wage range, if applicable) that Sentry reasonably expects to pay for this position is $240,000 to $400,000. A successful candidate’s actual base salary (or hourly wage) amount will be determined by a variety of relevant factors including, without limitation, the candidate’s work location, education, work and other relevant experience, skills, and job-related knowledge. A successful candidate will be eligible to participate in Sentry’s employee benefit plans/programs applicable to the candidate’s position (including incentive compensation, equity grants, paid time off, and group health insurance coverage). See Sentry Benefits for more details about the Company’s benefit plans/programs.

Equal Opportunity at Sentry

Sentry is committed to providing equal employment opportunities to its employees and candidates for employment regardless of race, color, ancestry, religion, sex, national origin, sexual orientation, age, citizenship, marital status, disability, gender identity, veteran status, or other legally-protected characteristic. This commitment includes the provision of reasonable accommodations to employees and candidates for employment with physical or mental disabilities who require such accommodations in order to (a) perform the essential functions of their jobs, or (b) seek employment with Sentry. We strive to build a diverse team, with an inclusive culture where every teammate can thrive. Sentry is an open-source company because we believe that everyone, everywhere, should have the ability and tools to make great software. Software should be accessible. That starts with making our industry accessible.

• Invest in your future with company match!
  (USandCanadaonly)
• Because you can never be too prepared.
• Commuter Stipend
• You shouldn't have to pay to get to work.
• Professional Development Stipend
• Keep your skills sharp. You'll need them.
• Stay healthy, stay happy, do
  yoga or something.
• Charitable Matching Program
• You're a good person. We like that.
• Flexible PTO
• You work, we pay. You take time off, we still pay.