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: 1+ year 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 Go (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
Working at DriveWealth
We do our best work when we're in the same room. To maintain the speed our partners expect, our New York, Chicago, and Lithuania teams work in office on a hybrid schedule. We've found that being physically side-by-side is the only way to solve complex problems in real-time and stay truly accountable to the products we ship. When you're here, you're working directly with the people making the decisions.
To support that work, we provide competitive compensation, equity, and a 401(k) match. We also offer Medical insurance, Dental insurance, Vision insurance, Disability insurance, and Paid Parental Leave, along with a wellness reimbursement, a company-provided phone, and a personal development allowance. Finally, we value the time you spend away from the office with generous Paid Time Off (PTO) and observed holidays.
Work Authorization
Applicants must possess the legal right to work in the country where the position is located at the time of application. DriveWealth requires all employees to provide original documentation verifying their work authorization on or before their first day of employment.
For US-based roles: Applicants must be currently authorized to work in the United States on a full-time basis without the need for current or future visa sponsorship. DriveWealth does not provide visa sponsorship or support for employment authorization, including transfers, at this time. Offers of employment are strictly contingent upon an individual’s ability to secure and maintain the legal right to work at the Company.
How We Think About AI
We leverage AI to work smarter and move faster. We seek AI-curious talent who are proactive about using emerging tools to increase signal quality, reduce friction, and improve outcomes to deliver products faster, provide better service to our partners, and to streamline processes. Your ability to leverage our internal tools and technology to drive results is as important to us as your core domain expertise.
Compensation
Pay is generally based on the level, complexity, responsibility, location, and job duties/requirements of the specific position. We then source candidates with the requisite skills, expertise, education, training, and experience. If you are selected for an interview, please feel welcome to speak to a recruiter about our compensation philosophy and other available benefits. This role is eligible for base, bonus, equity, 401(k) match, and heavily subsidized benefits and perks.
Equal Employment Opportunity
To build technology and products that are used and loved by people and solve real-world problems, we need to build a team with many different perspectives and experiences. We are an equal opportunity employer. We do not discriminate based on race, religion, color, national origin, gender, sexual orientation, age, marital status, veteran status, or disability status. We encourage candidates from all backgrounds to apply.
Agency Disclaimer
DriveWealth does not accept agency resumes. Do not forward resumes to our jobs alias, employees, or any other organization location. DriveWealth is not responsible for any fees related to unsolicited resumes.
