Lead Software Engineer (remote)

In this role, you will lead the design, enhancement, and modernization of a point-of-sale platform—driving version upgrades, strengthening configuration frameworks, improving observability, and ensuring high availability and compliance across a distributed retail environment. This position is well-suited for engineers who excel in fast-paced retail environments, enjoy solving complex system challenges, and are motivated to deliver high-quality solutions at scale.

We are seeking a Lead Engineer with deep technical expertise in Oracle Xstore (POS & Back Office) and a strong focus on building scalable, resilient retail store systems. In this role, you will lead the design, enhancement, and modernization of a point-of-sale platform—driving version upgrades, strengthening configuration frameworks, improving observability, and ensuring high availability and compliance across a distributed retail environment.

This role serves as a key technical leader, partnering cross-functionally with architecture, security, infrastructure, operations, field support, and external vendors to deliver foundational improvements that enhance performance, reduce downtime, and support long-term platform sustainability.

This position is well-suited for engineers who excel in fast-paced retail environments, enjoy solving complex system challenges, and are motivated to deliver high-quality solutions at scale.

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Key Responsibilities

Core Platform Engineering & Modernization

• Lead development, enhancement, and lifecycle management of Oracle Xstore systems with a focus on stability, scalability, and maintainability.
• Drive platform upgrades, patching strategies, dependency modernization, and technical debt reduction through structured rollout plans.
• Enhance configuration management capabilities, including store-level overrides, multi-tenant considerations, and flexible configuration models.
• Design and implement foundational services, frameworks, and extensibility points to support broader engineering teams.

Compliance, Reliability & Global Enablement

• Support implementation of region-specific compliance requirements, including fiscalization, tax handling, receipt standards, and data privacy considerations.
• Collaborate with cross-functional teams to align with regulatory and operational requirements across multiple markets.
• Improve platform resilience, including startup reliability, failover handling, and recovery processes.

Observability & Operational Excellence

• Advance observability practices across the POS ecosystem, including logging, monitoring, tracing, health checks, and alerting.
• Develop tools and capabilities to improve diagnostics, troubleshooting, and automated recovery.
• Lead incident response efforts and post-incident reviews to improve system reliability and reduce resolution times.

Collaboration & Leadership

• Provide technical leadership and mentorship to engineering teams.
• Drive architectural decisions, promote best practices, and identify opportunities for foundational improvements.
• Partner across teams and with external vendors to support design reviews, implementations, and rollout strategies.

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Minimum Qualifications

• 7+ years of engineering experience, with strong expertise in Oracle Xstore (POS and Back Office), including customization and environment management.
• Demonstrated experience with platform upgrades, patching, migrations, and modernization initiatives.
• Deep understanding of retail POS operations, system workflows, and store-level constraints.
• Strong proficiency in Java, RESTful services, and integration patterns for distributed systems.
• Experience implementing observability solutions, including logging, monitoring, and alerting frameworks.
• Proven ability to lead complex technical initiatives involving multiple stakeholders.
• Strong communication skills and ability to collaborate across technical and operational teams.

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Preferred Qualifications

• Experience supporting international POS deployments with varying regulatory and compliance requirements.
• Knowledge of store networking, deployment models, and offline/failover strategies.
• Familiarity with performance optimization, system startup tuning, and large-scale rollout coordination.
• Experience with automation tools and scripting (e.g., PowerShell, Bash, Python).
• Background in modernizing legacy retail systems or building scalable platform frameworks.

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