Associate Site Reliability Engineer

The FreedomPay Commerce Platform is the technology of choice for many of the largest companies across the globe in retail, hospitality, lodging, gaming, sports and entertainment, foodservice, education, healthcare and financial services. FreedomPay’s technology has been purposely built to deliver rock solid performance in the highly complex environment of global commerce. The company maintains a world-class security environment and was first to earn the coveted validation by the PCI Security Standards Council against Point-to-Point Encryption with EMV standard in North America. FreedomPay’s robust solutions across payments, security, identity and data analytics are available in-store, online and on-mobile and are supported by rapid API adoption. The award winning FreedomPay Commerce Platform operates on a single, unified technology stack across multiple continents allowing enterprises to deliver a consistent, repeatable experience on a global scale. FreedomPay is a fast paced, high growth company with a great culture with competitive benefits and compensation with a business casual atmosphere.

FreedomPay is seeking an experienced Senior Site Reliability Engineer to help ensure the highest possible availability and resiliency of a rapidly growing global payment platform. This full-time salaried position builds on a strong foundation of observability, incident response, and support experience across the development lifecycle — and pushes it forward with AI-driven operations and automation at its core. The right candidate finds real satisfaction in eliminating manual toil, treats every recurring task as an automation opportunity, and is eager to apply modern AI tooling to detect, diagnose, and resolve issues faster than ever before.

About the Role

You'll join a team focused on improving platform reliability and reducing operational overhead through automation and AI-driven tooling. This role provides hands-on exposure to modern observability platforms, cloud technologies, incident response processes, and AI-assisted engineering practices.

We're looking for someone who

• Enjoys solving technical problems and learning new technologies.
• Seeks opportunities to automate repetitive work.
• Has experience using AI tools to improve productivity and troubleshooting.
• Is excited about building a career in Site Reliability Engineering, Platform Engineering, or Cloud Operations.

This position participates in an on-call rotation with mentorship and support from senior team members.

Primary Responsibilities

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• Learn and develop a strong understanding of FreedomPay's platform and application ecosystem.
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• Work directly with development teams to integrate observability into FreedomPay products as they are being built.
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• Implement AI tools to accelerate troubleshooting, documentation, reporting, and automation development.
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• Support monitoring improvements through alert tuning, dashboard development, and observability enhancements.
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• Build and maintain automation scripts and workflows that reduce manual operational effort.
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• Investigate alerts, identify root causes, and collaborate with senior engineers on remediation efforts.
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• Troubleshoot scheduled jobs, integrations, and data-processing issues.

AI Enablement & Automation

AI and automation are core components of how our engineering teams operate. In this role, you will

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• Use AI-assisted development tools such as Claude, ChatGPT, Azure AI services, or similar technologies to improve productivity.
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• Build agents that will create and maintain observability standards across multiple development teams and applications.
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• Apply AI tools to investigate incidents, analyze logs, and accelerate root-cause analysis.
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• Experiment with AI-powered observability capabilities such as anomaly detection and intelligent alerting.
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• Learn best practices for responsible AI usage in a highly regulated payment-processing environment.
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• Contribute to a culture of continuous improvement through automation, AI experimentation, and knowledge sharing.

Required Background and Experience

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• Bachelor's degree in Computer Science, Information Technology, Engineering, or a related field, or equivalent practical experience.
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• 1-3 years of technical experience in software engineering, cloud operations, infrastructure support, DevOps, platform operations, or a related discipline.
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• Strong desire to learn new technologies and continuously develop technical skills.
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• Demonstrated interest in AI, automation, scripting, or cloud technologies.
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• Strong analytical and problem-solving skills.
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• Excellent communication and collaboration skills.
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• Ability to work effectively in a fast-paced environment and manage multiple priorities.

Required Technical Skills

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• Familiarity with monitoring or observability platforms such as Dynatrace, Datadog, New Relic, Splunk, or similar tools.
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• Experience using AI-powered productivity, coding, or troubleshooting tools.
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• Basic scripting experience with Python, PowerShell, or another programming language.
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• Foundational SQL knowledge.
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• Basic understanding of networking concepts including DNS, HTTP/HTTPS, TCP/IP, and load balancing.
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• Familiarity with cloud platforms such as Azure, AWS, or Google Cloud.
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• Understanding of software development lifecycle concepts and modern application architectures.

Preferred Technical Skills and Experience

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• Internship, coursework, or hands-on experience related to cloud infrastructure, DevOps, SRE, or platform operations.
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• Experience using Git, CI/CD pipelines, or Infrastructure as Code tools.
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• Exposure to containers and Kubernetes.
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• Experience building small automations, scripts, or AI-powered workflows.
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• Familiarity with Azure AI Foundry, Claude, ChatGPT, or similar AI technologies.
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• Experience supporting customer-facing or transaction-processing systems.