Staff Software Engineer, Observability

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About Gusto

At Gusto, we're on a mission to grow the small business economy. We handle the hard stuff—like payroll, health insurance, 401(k)s, and HR—so owners can focus on their craft and customers. With teams in Denver, San Francisco, and New York, we’re proud to support more than 400,000 small businesses across the country, and we’re building a workplace that represents and celebrates the customers we serve. Learn more about our Total Rewards philosophy.

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.