Staff Software Engineer, Backend (Observability)

Description

The company offers a way for people to pay over time with no hidden fees.

The Observability team builds the platform engineers use to see how the company's systems behave and perform. It takes in more than 200 TB of metrics, logs, and traces per day from hundreds of services across over 80 Kubernetes clusters. When a checkout fails, this data is how engineers learn the cause.

Over the coming year the team is moving to wide events, where each request produces one event with full context, so debugging gets faster with less noise. The team is also adding log sampling and writing observability practices into agentic development and code review, so AI-written code arrives with good instrumentation.

This is a Staff Software Engineer role leading the team's technical direction. Most of your time is hands-on coding. You will set the roadmap, lead cross-functional projects, mentor a team of six engineers, and work closely with infrastructure and product teams.

Responsibilities

• You will own the design of the telemetry pipeline, weighing reliability, query speed, and cost at more than 200 TB per day.
• You will design log sampling approaches that cut volume and spend substantially while keeping the data engineers need during incidents.
• You will shape how observability fits into agentic development, so AI coding agents and code review flag missing instrumentation before code ships.
• You will set the team's technical strategy on a one-year horizon and connect it to high-impact business projects.
• You will work with product management, design, and analytics across the product lifecycle, making sure technical sustainability, risks, and trade-offs are understood and handled.
• You will multiply the team's impact by defining and promoting technical solutions and operating processes.
• You will take responsibility for the team's uptime and operations, putting in place monitoring, triage rotations, playbooks, policies, testing, and alerting to support routine upkeep and on-call work.
• You will build a culture of quality and ownership by setting code review and design standards, and promoting them beyond the team through writing and tech talks.
• You will grow people on the team through feedback, guidance, and by setting an example.

Requirements

• You have 8+ years of experience designing, building, and launching backend systems at scale in languages such as Python or Kotlin.
• You have a deep history of building highly available distributed systems with tools such as AWS, MySQL, Flink, and Kubernetes.
• You have built or run high-volume telemetry systems for metrics, logs, or traces, using tools such as OpenTelemetry, Kafka, and Terraform.
• You hold a well-reasoned view on modern observability practice, including structured and wide events, sampling, cardinality management, and SLOs.
• You have led a platform standard into use across many engineering teams through both tooling and outreach.
• You have delivered major features or system components, or retired existing functionality, through a written technical and execution plan. You write clear, high-quality code that others can understand and reuse.
• You are comfortable working with ambiguity and can move from low-level language details up to the architecture of large systems to see how they work.
• You have a strong record of collecting feedback from engineering and cross-functional peers and acting on it over time.
• You communicate clearly in speech and writing, supporting work with the company's global engineering team.

Conditions

Equity grade 7.

New hires usually start near the bottom of the pay range. Pay is set by location, experience, and job skills, using a clear and open structure.

Base pay is part of total compensation, which may also include monthly stipends for health, wellness, and tech, plus benefits such as fully subsidized medical, dental, and vision coverage for you and your dependents. You may also be eligible for equity from the parent company, the company Holdings, Inc.

Canada base pay range: $181,000 to $241,000 per year.

This is a remote role open only to people living in Alberta, British Columbia, Manitoba, New Brunswick, Newfoundland and Labrador, Nova Scotia, Ontario, Prince Edward Island, or Saskatchewan.

The company is remote-first. Most roles can be done from nearly anywhere in the country of employment, some need occasional in-person work at an office, and a few are office-based. All new hires are invited to an in-person onboarding.

Accommodations are available during interviews for candidates with disabilities, and for roles in San Francisco or Los Angeles, qualified applicants with arrest and conviction records are considered as required by law.

Benefits

• Health coverage costs you nothing, as the company pays 100% of premiums for you and your dependents.
• Monthly stipends cover your tech setup and let you pick health and wellness options that suit you.
• Flexible time off and generous holiday schedules give you room to rest.
• An employee stock purchase plan (ESPP) lets you buy company stock at a discount.