[Remote] Principal Site Reliability Engineer

Note: The job is a remote job and is open to candidates in USA. Upstart is a leading AI lending marketplace on a mission to reduce the cost and complexity of borrowing for all Americans. They are seeking a Principal Site Reliability Engineer to lead the SRE team in ensuring the reliability and observability of their production systems while driving best practices and collaborating with cross-functional teams to enhance operational excellence.

Responsibilities

• Lead the definition, advocacy, and adoption of SRE principles across engineering teams
• Partner with leadership to shape long-term reliability, resiliency, and observability strategies
• Champion distributed tracing, real user monitoring (RUM), and key performance metrics such as Largest Contentful Paint (LCP) to improve system visibility and user experience
• Build and scale self-healing systems to minimize manual intervention and reduce downtime
• Drive enterprise-wide improvements to incident response processes, including those related to Machine Learning systems
• Collaborate closely with Development Productivity and Quality teams to improve engineering velocity without sacrificing reliability
• Influence technical and operational roadmaps through data-driven insights and hands-on technical contributions
• Own and deliver cross-functional initiatives from concept through execution, applying program management skills to align stakeholders and achieve results

Skills

• Bachelor's degree in Computer Science, Engineering, or Mathematics, or a related field (or its equivalent) + 8 years of experience
• Combined experience with both Software Engineering and Site Reliability Engineering, with a balanced background in both disciplines
• Proven track record as an SRE thought leader and evangelist, driving adoption of reliability best practices across organizations
• Strong communication and mentoring skills to influence engineers across disciplines
• Proficiency in Python, Go, JavaScript/TypeScript
• Proficiency with Infrastructure as Code (Terraform, CDK, CloudFormation, etc.)
• Experience building internal tooling from scratch in agile development environments
• Expertise with observability, distributed tracing, RUM, LCP, and performance monitoring tools (e.g., Datadog, Prometheus)
• Experience with on-call and incident management, including large-scale or ML-related incidents
• Strong background in automation and building self-healing systems
• Hands-on experience with LLM/GenAI to improve SRE efficiency and processes
• Program management skills, including the ability to propose innovative solutions, influence leadership, improve processes, and drive cross-functional projects to completion
• Experience with service mesh
• Full stack development skills
• Experience building or extending observability platforms
• Background in Development Productivity or Quality Platforms
• Experience in high-scale SaaS, microservice-oriented cloud environments

Benefits

• Target bonuses
• Equity compensation
• Generous benefits packages (including medical, dental, vision, and 401k)
• Competitive compensation, including base pay, bonus opportunities, and annual equity grants that vest quarterly
• Retirement benefits to help you plan for the future, including a 401(k) or Group Retirement Savings Plan with a company match of $2 for every $1 contributed, up to $15,000 annually (USD in the US, CAD in Canada)
• Employee Stock Purchase Plan (ESPP) with discounted stock purchase options for eligible employees (US only)
• Comprehensive health coverage designed to support you and your family, including medical, dental, vision, and wellness resources for US and supplemental health coverage for Canada.
• Health Savings Account contributions from Upstart for eligible plans (US only)
• Income protection benefits, including life insurance and disability coverage for added financial security
• Paid time off, sick leave, and company holidays, in line with local requirements
• Paid family and parental leave to support caregiving and major life moments (duration varies by country)
• Family-centered benefits to support fertility, parenthood, and caregiving needs
• Employee Assistance Program (EAP) offering mental health support and life-centered resources
• Financial wellness resources, including access to financial planning tools and a financial concierge service (US Only)
• Annual wellness allowance to support your physical and emotional well-being and personal development, based on what matters most to you
• Annual productivity allowance to invest in relevant tools and resources you need to do your best work, no matter where you work from
• Connection and community through team events, a

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