Staff Software Engineer, Observability

Gusto

🔍 Observed

San Francisco, CA First seen 1 day, 4 hours ago Last seen 4 hours, 33 minutes ago Greenhouse

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Job Description

AI Summary

• Lead the design and evolution of Gusto's observability platform, including distributed logging, metrics, and tracing infrastructure using tools like Datadog and Kubernetes • Build AI-native capabilities to automatically detect anomalies, diagnose failures, and accelerate root cause analysis across the engineering organization • Require proven experience operating large-scale distributed systems in production, with strong fundamentals in systems, networking, cloud infrastructure (AWS/Kubernetes), and ideally logging platforms or time series databases • Partner with engineering teams to establish observability standards, mentor engineers, and drive reliability culture while creating developer-friendly dashboards and debugging tools • Competitive base pay, equity (RSUs), and comprehensive benefits; team locations in Denver, San Francisco, and New York

About Gusto

At Gusto, we're on a mission to grow the small business economy. We handle the hard stuff — payroll, health insurance, 401(k)s, and HR — so owners can focus on their craft and their customers. With teams in Denver, San Francisco, and New York, we support more than 500,000 small businesses nationwide and are building a workplace that reflects the people we serve.

All full-time employees receive competitive base pay, benefits, and equity (RSUs) — because everyone who helps build Gusto should share in its success. Offer amounts are determined by role, level, and location. Learn more about our Total Rewards philosophy.

AI is a fundamental part of how work gets done at Gusto. We expect all team members to actively engage with AI tools relevant to their role and grow their fluency as the technology evolves. AI experience requirements vary by role and will be assessed during the interview process.

Staff Observability Engineer

Gusto’s Reliability Engineering team enables our product teams to build impactful products by building secure, resilient, and accessible systems, using tools like AWS, Terraform, Datadog, and Kubernetes.

About Gusto

Gusto is a modern, online people platform that helps small businesses take care of their teams. On top of full-service payroll, Gusto offers health insurance, 401(k)s, expert HR, and team management tools. Today, Gusto offices in Denver, San Francisco, and New York serve more than 200,000 businesses nationwide.

Our mission is to create a world where work empowers a better life, and it starts right here at Gusto. That’s why we’re committed to building a collaborative and inclusive workplace, both physically and virtually. Learn more about our Total Rewards philosophy.

What You’ll Do

Shape the engineering organization standards around observability.
Own and evolve the observability platform, including distributed logging, metrics, and tracing infrastructure.
Build AI-native capabilities to automatically detect anomalies, diagnose failures, and accelerate root cause analysis.
Create powerful developer experiences through dashboards, notebooks, and interactive debugging tools.
Drive reliability automation with intelligent alerting, diagnostics, and incident response systems.
Partner across engineering teams to embed observability and reliability best practices.
Mentor engineers and influence reliability culture across the organization.

What We’re Looking For

Strategic systems thinker who identifies high impact opportunities and builds scalable solutions.
Experience operating large scale distributed systems in production, especially logging platforms or time series databases.
Strong fundamentals in systems, networking, and cloud infrastructure such as Kubernetes and AWS.
Thrive in ambiguous environments and roll up your sleeves to solve unscoped problems end to end.
Product mindset or full stack instincts and excited to build real tools engineers love to use.
Strong communicator who can align technical and non technical stakeholders.
Bonus if you have built or contributed to observability ecosystems such as OpenTelemetry or Prometheus

Required Experience

Have 8+ years of relevant industry experience building and operating large-scale observability or monitoring infrastructure
Experience implementing or operating observability platforms such as Datadog, Sentry, Splunk, or similar.
Have strong SWE coding proficiency in at least one of Ruby, Python, or TypeScript.

Preferred Experience

Cloud infrastructure experience (AWS preferred).
Infrastructure-as-Code, such as Terraform or Crossplane.
Container orchestration, such as Kubernetes.
Linux systems knowledge and shell proficiency.
Experience designing highly available and scalable systems.
Experience acting as an internal consultant or trusted advisor.

Our cash compensation amount for this role is targeted at $200,000-$230,000 /yr in Denver & most remote locations, and $230,000-$270,000 /yr for San Francisco, Seattle & New York. Final offer amounts are determined by multiple factors, including candidate experience and expertise, and may vary from the amounts listed above.

Gusto has physical office spaces in Denver, San Francisco, and New York City. Employees who are based in those locations will be expected to work from the office on designated days approximately 2-3 days per week (or more depending on role). The same office expectations apply to all Symmetry roles, Gusto's subsidiary, whose physical office is in Scottsdale.

Note: The San Francisco office expectations encompass both the San Francisco and San Jose metro areas.

When approved to work from a location other than a Gusto office, a secure, reliable, and consistent internet connection is required. This includes non-office days for hybrid employees.

Our customers come from all walks of life and so do we. We hire great people from a wide variety of backgrounds, not just because it's the right thing to do, but because it makes our company stronger. If you share our values and our enthusiasm for small businesses, you will find a home at Gusto.

Gusto is proud to be an equal opportunity employer. We do not discriminate in hiring or any employment decision based on race, color, religion, national origin, age, sex (including pregnancy, childbirth, or related medical conditions), marital status, ancestry, physical or mental disability, genetic information, veteran status, gender identity or expression, sexual orientation, or other applicable legally protected characteristic. Gusto considers qualified applicants with criminal histories, consistent with applicable federal, state and local law. Gusto is also committed to providing reasonable accommodations for qualified individuals with disabilities and disabled veterans in our job application procedures. We want to see our candidates perform to the best of their ability. If you require a medical or religious accommodation at any time throughout your candidate journey, please fill out this form and a member of our team will get in touch with you.

Gusto takes security and protection of your personal information very seriously. Please review our Fraudulent Activity Disclaimer.

Personal information collected and processed as part of your Gusto application will be subject to Gusto's Applicant Privacy Notice.

Skills

rust kubernetes go terraform typescript python aws

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Job Information

Company:
Gusto
Location:
San Francisco, CA
Job Type:
Internship
Work Location:
Remote
Experience Level:
Executive
Source:
Greenhouse
Status:
Active

Activity Score

78 /100

Likely Active (78)

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