Manager, Site Reliability Engineering

Manager, Site Reliability Engineering

Office - Chicago

DriveWealth is on a mission to make investing easier. We believe that everyone should have the ability to control their financial future, and that access to financial markets should not be limited by geography, wealth, or legacy systems. We are a global B2B financial technology organization dedicated to democratizing access to financial independence around the world. Our mission is realized through an API-based platform, empowering our partners to offer seamless investing and trading experiences to clients worldwide, all from their mobile devices. Our technology provides partners with a modern, extensible toolkit, enabling traditional investment workflows and innovative techniques like fractional share ownership. DriveWealth has evolved into a global platform offering trading of US equities, mutual funds, ETFs, fixed income, and options.

There's never been a better time to build a category-defining business and there has rarely been a team better positioned for this opportunity. Our culture blends the pace and agility of a fintech start-up with the impact, stability, and discipline of Wall Street. We encourage creativity and experimentation while ensuring institutional-grade execution and regulatory compliance in everything we do. Join us and help build the future of global investing!

About The Role

As the Manager of Site Reliability Engineering, you'll lead a team of SRE Automation Engineers while remaining a hands-on technical authority for our Brokerage-as-a-Service platform. This isn't a purely people-management seat, you're expected to bring the same principal-level SRE depth to automation design and engineering as an individual contributor, while also building the team, setting technical direction, and developing your engineers' careers.

This role is centered on reducing manual toil through engineering, applying Google's SRE principles: SLOs, error budgets, blameless postmortems, and systematic toil reduction, adapted to a regulated brokerage environment. You'll carry two responsibilities at once: driving the automation agenda, building and orchestrating workflows in Rundeck and Airflow to eliminate repetitive work, and growing your team of SRE Automation Engineers into a high-functioning automation practice. You'll guide the design of internal SRE platforms, automate complex workflows, and ensure our Kubernetes-based and colo ecosystems can handle the demands of global financial markets, while owning the people side of the team: mentorship, performance, and growth, and the day-to-day management of the team's Jira board. While this role includes participation in on-call rotations supporting our 24/7 global operations, your primary mission is to build systems that make manual intervention obsolete, and a team capable of sustaining that mission.

What You'll Do

• Team Leadership & Development: Manage, mentor, and grow a team of SRE Automation Engineers—setting technical direction, running 1:1s, owning performance management and career development, and managing the team's Jira board to prioritize and track sprint work.
• Engineering & Automation: Lead the design and development of internal tooling and automation—including Rundeck and Airflow-based orchestration—to eliminate repetitive manual toil and improve developer velocity, staying hands-on with the most complex, highest-leverage automation work yourself.
• SRE Practice & Governance: Adapt Google's SRE principles to our environment—defining SLIs, SLOs, and error budgets, and using them to guide engineering and operational priorities.
• Infrastructure as Code: Set architectural standards for modular, reusable IaC using Terraform and oversee GitOps workflows via ArgoCD.
• Platform Governance: Review software architecture and Kubernetes metrics to ensure high availability, capacity planning, and cost-optimization across AWS regions, and hold the team accountable to those standards.
• Incident Engineering: Lead incident response for critical events, drive complex root-cause analysis (RCA), and champion a blameless post-mortem culture across the organization.
• Collaboration & Stakeholder Management: Partner with engineering leadership to align SRE priorities with business goals, and foster adoption of new tools, security standards, and reliability best practices across teams.

You Bring

• People Leadership: Prior experience managing or leading SRE/DevOps engineers, ideally in a fintech or highly regulated environment. Able to flex between hands-on principal-level engineering and coaching and developing a team.
• Google SRE Fundamentals: Working knowledge of Google's SRE practices—SLIs/SLOs, error budgets, toil reduction, and blameless postmortems—and experience adapting them to a regulated environment.
• Linux & Networking Mastery: Proficient in Linux administration with a deep understanding of the TCP/IP stack, OSI model, DNS, and network troubleshooting.
• FinTech Background: Experience working in highly regulated financial environments or with FIX/API connectivity.
• Production Kubernetes: Hands-on experience managing production-grade clusters, including RBAC, autoscaling, Helm, and multi-cluster patterns.
• Cloud Native Expertise (AWS): Strong grasp of AWS core services, security, and high-availability patterns. Proficiency with boto3 and AWS CLI for automation.
• Modern CI/CD & GitOps: Experience building secure, automated delivery pipelines and operating GitOps workflows (ArgoCD).
• Code Proficiency: Strong scripting and development skills in Python or Golang, along with Bash and Ansible.
• Observability: Experience with Grafana/Similar tools, Prometheus, Understanding of logs shipping, management and metric first alerting.
• Security Mindset: Experience with secrets management, vulnerability scanning, and securing the software supply chain.
• AI & Prompt Engineering: Familiarity with using LLMs, Public MCPs, or Bedrock Agent Core to enhance SRE workflows.
• Data & Middleware & Orchestration: Hands-on experience with Rundeck and Airflow for job orchestration and automation, plus experience managing Kafka, MQ, or SQS.

Location

This role is open to candidates in the following locations: Chicago, IL - Hybrid

• This role is expected to come into the office on a cadence set by the Hiring Manager/Team.
• If you're not based in the location listed above, this role is not a fit, and we cannot accommodate remote work outside these locations.
• Applicants must be authorized to work for any employer in the U.S. DriveWealth does not sponsor or take over sponsorship of an employment visa at this time.

Pay Range: $150,000 – $170,000 USD