Headquarters: Remote, United States

Director of Production Engineering 

Remote, United States

About this Position

Are you passionate about building the reliability, automation, and security foundations that let engineering teams move fast with confidence? At Legion, we are seeking a Director of Engineering, DevOps & SRE to lead the teams responsible for the availability, scalability, and security of our production environment. Our production infrastructure runs on AWS, leveraging services such as EKS, RDS, and a broad set of AWS-native technologies. You will partner closely with engineering and IT to build resilient systems, drive operational excellence, and ensure our platform meets the highest standards of security and compliance.

This is a hands-on leadership role where you'll spend ~20-30% of your time contributing directly to architecture, tooling, and incident response, and the rest driving vision, roadmap, and cross-team execution.

Responsibilities

• Hire and build a globally-distributed DevOps/SRE engineering team. Recruit, mentor, and manage engineers, and foster a culture of ownership, collaboration, and continuous improvement.
• Own the reliability and infrastructure roadmap for our AWS-based production environment, including EKS, RDS, and related AWS services, ensuring scalability, high availability, and cost efficiency.
• Lead the organization's security operations (SecOps) practice, including vulnerability management, threat detection, incident response, and remediation, to proactively identify and resolve security issues before they impact customers.
• Define and drive engineering OKRs for infrastructure reliability, automation, and security, and track progress against measurable outcomes.
• Champion observability and alerting best practices (e.g., Datadog), including automating alert triage and response to reduce mean-time-to-resolution.
• Solid understanding of agentic AI infrastructure and how AI agentic workflows apply to SDLC and DevOps processes (e.g., automated investigation, remediation, and PR-generation pipelines).
• Drive Infrastructure-as-Code, CI/CD, and automation practices to increase engineering velocity and reduce operational toil.
• Work closely with engineering and IT teams to align on infrastructure standards, access controls, tooling, and compliance requirements across the organization.
• Ensure the platform meets the highest standards of security, compliance, and data protection; implement and maintain robust security controls and audit-readiness.
• Lead and participate in the Incident Management on-call rotation, working with SRE and development teams to meet and exceed availability goals.
• Stay current on cloud, DevOps, and security best practices, and provide technical guidance and thought leadership to the broader engineering organization.

Required Qualifications

• 8-12 years of experience in DevOps, Site Reliability Engineering, or production infrastructure roles, including people management experience.
• Deep hands-on experience running production workloads on AWS, including EKS (Kubernetes), RDS, and other core AWS services (e.g., VPC, IAM, Lambda, S3).
• Demonstrated experience running security operations (SecOps) — vulnerability management, incident response, and remediation of production security issues.
• 5+ years of experience leveraging observability platforms (e.g., Datadog, Prometheus, Grafana) to drive reliability, performance, and alerting improvements.
• Strong experience with Infrastructure-as-Code (e.g., Terraform, CloudFormation) and CI/CD automation.
• Proficiency in at least one of Go, Python, or Bash, with day-to-day use of Git and test automation pipelines.
• Hands-on experie

Headquarters: Remote, United States

Chief Architect

Remote - US

Legion Technologies is building the AI-powered operating system for the hourly workforce. We are hiring a Chief Architect to serve as Legion’s most senior hands-on technical leader and to shape the technical foundation that will power the next decade of product innovation.

This is not a strategy-only or advisory role. The Chief Architect must live close to the code, go deep with engineering teams, challenge assumptions, write and review technical designs, make high-consequence architecture decisions, and help turn bold product ambitions into scalable, reliable production systems.

This person will own architecture and technical decision-making for the most complex parts of Legion’s Workforce Management platform, including AI, optimization, forecasting, scheduling, distributed systems, data platforms, real-time decisioning, enterprise scalability, security, compliance, and developer productivity.

The ideal candidate has built and scaled mission-critical software used by large enterprise customers, has deep technical credibility with senior engineers, and can operate fluidly between code-level decisions and long-term platform strategy. They are pragmatic, decisive, opinionated, and comfortable making hard tradeoffs when simplicity, scalability, reliability, or customer trust require it.

This role reports to the Head of Product, Engineering, and Support. This is an open role currently being filled on an interim basis by the CEO.

Responsibilities and Duties

Hands-On Architecture and Technical Decision-Making

Serve as Legion’s senior-most hands-on technical authority for complex architecture, system design, and platform evolution.

• Personally dive into code, design documents, production incidents, performance bottlenecks, and implementation tradeoffs to diagnose root causes and guide technical direction.
• Lead the hardest technical decisions across AI systems, optimization engines, distributed systems, data architecture, reliability, scalability, security, and platform modernization.
• Write prototypes, reference implementations, architecture decision records, technical specifications, and design patterns where needed to unblock teams and establish clear direction.
• Make high-consequence technical decisions with incomplete information, balancing correctness, simplicity, speed, scalability, reliability, cost, and long-term maintainability.
• Challenge architectural drift, unnecessary complexity, weak abstractions, and short-term decisions that create long-term platform risk.
• Partner directly with Staff, Principal, and senior engineering leaders in design reviews, code-level discussions, and implementation planning.

Platform Architecture and Technical Vision

• Define and own the long-term architecture for Legion’s AI-driven Workforce Management platform across application services, data infrastructure, ML systems, optimization engines, APIs, integration architecture, developer platforms, and enterprise-scale operations.
• Establish engineering-wide standards for system design, scalability, performance, reliability, extensibility, observability, security, and maintainability.
• Serve as the final architectural authority for major platform initiatives and technical decisions with long-term consequences.
• Identify opportunities to reduce complexity, improve system efficiency, accelerate engineering velocity, and unlock new product capabilities.
• Proactively surface technical debt, architectural risk, and platform constraints before they compound into customer, product, or engineering velocity issues.
• Create pragmatic migration pat