[Remote] Sr. Site Reliability Engineer

Note: The job is a remote job and is open to candidates in USA. FreedomPay is a fast paced, high growth company providing a global payment platform technology. They are seeking an experienced Senior Site Reliability Engineer to ensure the highest possible availability and resiliency of their platform, focusing on observability, incident response, and automation.

Responsibilities

• Build and maintain a comprehensive understanding of the platform and custom application stack
• Implement, maintain, and continuously improve observability strategies and metrics that ensure complete system health for numerous complex products throughout all stages of the development lifecycle, up to and including production
• Continuously identify automation opportunities and follow through to successful implementation, applying AI-assisted tooling to accelerate development and reduce manual effort
• Design, build, and maintain automated remediation and self-healing workflows that detect, triage, and resolve common failure modes with minimal human intervention
• Leverage AI/ML-driven observability — anomaly detection, alert correlation, and intelligent noise reduction — to surface issues earlier and shorten time to detection
• Use AI-assisted analysis to accelerate root-cause investigation, enrich incident context, and generate first-draft postmortems and runbooks for human review
• Handle escalations and collaborate effectively with other team members to quickly determine the root cause of any type of service degradation
• Implement, maintain, and continuously improve incident response procedures and other operational documentation, automating documentation generation and upkeep wherever practical
• Assist with troubleshooting and remediation of failed scheduled jobs and data-related concerns
• Champion responsible, secure adoption of AI tooling across the SRE function — sharing patterns, prompts, and automations that raise the productivity of the whole team
• Apply AI-assisted development and operations tools — including Anthropic (Claude), OpenAI (Codex), and Azure AI services (Foundry, Azure SRE Agent) and the agentic workflows built on them — to write, review, and accelerate automation and infrastructure code
• Build and integrate automation that turns repetitive operational work into codified, repeatable, and self-service workflows
• Use AIOps and ML-driven observability capabilities within the APM stack for anomaly detection, predictive alerting, and alert correlation
• Develop and refine prompts, agents, and integrations that connect monitoring, ticketing, and remediation systems into faster end-to-end response loops
• Evaluate emerging AI tooling for reliability and operations use cases, and advocate for adoption where it delivers measurable improvements in toil reduction, MTTR, or availability
• Ensure all AI and automation usage adheres to FreedomPay’s security, privacy, and PCI obligations — keeping sensitive data appropriately protected and human review in place for high-impact actions

Skills

• BS degree in Computer Science or equivalent, or equivalent years of relevant experience
• Minimum of 5 years of hands-on technical experience in highly available, high-throughput, web-based technology environments
• Demonstrated history of self-directed learning — someone who independently seeks out knowledge, builds new skills without being told to, and doesn't wait for formal training to close gaps
• Next-level problem-solving abilities and a strong bias toward practical, proven solutions
• A track record of identifying and eliminating manual toil through automation
• Excellent communication and organizational skills, with a strong sense of ownership and service
• Expert-level proficiency in an enterprise APM platform and its AI/ML-driven (AIOps) capabilities; Dynatrace experience strongly preferred, though deep expertise in comparable tools such as Datadog or New Relic where readily transferable
• Hands-on experience with AI-assisted development and automation tools — such as Anthropic (Claude), OpenAI (Codex), and Azure AI services (Foundry, Azure SRE Agent) — and a demonstrated ability to apply them to real operational and engineering work
• Proficiency in scripting and automation — PowerShell and/or Python — to build tooling and remediation workflows
• Strong SQL / T-SQL skills
• Solid understanding of core networking concepts: DNS, HTTP/HTTPS, load balancing, and TCP/IP routing and switching
• Working knowledge of modern technology infrastructure including container orchestration, IaaS/PaaS cloud services, Azure, and VMware
• Working knowledge of application development processes
• Proven track record of successfully implementing SLI/SLOs and fostering their adoption across an organization
• Experience implementing enterprise incident management practices
• Experience building AIOps or ML-driven automation into production observability and incident response
• Azure Kubernetes Service (AKS) and broader container orchestration experience
• Windows Server (IIS) administration
• PagerDuty Process Automation (formerly Rundeck) or comparable runbook automation platforms
• Comprehensive experience supporting real-time transaction processing applications
• PCI policies and best practices

Benefits

• Medical, prescription, dental and vision coverage
• Life Insurance
• Retirement Plans with company match
• Commission sharing plan
• Flexible hybrid working environment
• Great parental and other leave programs

Company Overview