Remote Python Automation Jobs in Naperville, IL (NOW HIRING)

FormativGroup is hiring an Engineering Manager to join a Financial Services technology organization that builds and maintains digital products for tax professionals. The team develops internal tools, financial dashboards, analytics, reporting solutions, and other technology that improves how client-serving professionals work.

This is a hands-on Engineering Manager role for an experienced technical lead who wants to step into people leadership without stepping away from delivery. You will serve as both the senior technical authority and the people leader: contributing code, setting technical direction, reviewing work, strengthening engineering practices, and helping the team use AI agents effectively across the software development lifecycle. The environment includes legacy .NET/C# services and Angular front ends alongside newer Python, Node.js, and React development. You will help modernize the stack in phases while keeping business-critical components stable.

• Lead from the keyboard: contribute production code regularly, use AI agents as part of day-to-day delivery, and stay close to the technical work.
• Own the team's technical direction, architecture decisions, long-term technical health, and roadmap across new delivery, modernization, and technical debt.
• Lead phased modernization of legacy .NET/C# and Angular components while building new capabilities with Python, Node.js, and React.
• Break work into small, well-bounded tasks and route each task to the best executor - an engineer, an agent, or yourself - while keeping coordination lean and outcome-focused.
• Own pull request review and provide fast, technically substantive feedback.
• Build and manage the technical-debt backlog, resolving priority issues directly instead of relying only on delegation.
• Hire, evaluate, coach, and grow engineers; set the technical hiring bar and help the team work effectively with AI agents.
• Create and maintain agent operating instructions, verification protocols, and human-in-the-loop controls for code, tests, documentation, and infrastructure changes.
• Run evaluation checks before merge and retain human-owned merge control for production branches.
• Maintain strong automated testing across unit, integration, and end-to-end layers, and uphold consistent engineering practices across design, coding, testing, release, and operations.
• Drive CI/CD automation, containerized delivery, and Infrastructure as Code for cloud-native applications.
• Track engineering health and delivery metrics, including required reporting through Atlassian Compass.
• Facilitate bi-weekly live demos from the cloud environment, including both product features and agent-enabled workflows.
• Partner with the dedicated production support organization by providing tooling, automation, documentation, and runbooks that make the product easier to operate and support.
• Reduce operational toil through automation while applying appropriate security guardrails, blast-radius limits, and audit trails to production-touching workflows.
• Maintain visibility into WIZ Critical and Major findings and drive remediation within required service levels.
• Keep architecture documentation, ADRs, runbooks, and agent instructions current and usable.

• 5-7+ years of relevant software engineering experience, with clear experience as a senior engineer or technical lead and prior leadership of at least one engineering team.
• Hands-on full-stack development depth and the desire to continue building while managing engineers.
• Strong proficiency with Python, Node.js, and React for modern application development.
• Experience maintaining and modernizing .NET/C# services and Angular front ends.
• Demonstrated use of agentic or AI-assisted software development workflows in real delivery environments, not just experimentation.
• Ownership of the full development lifecycle: build, test, release, operate, troubleshoot, and iterate.
• Cloud-native application experience on Azure; AWS or GCP experience is also relevant.
• Hands-on experience with containerized workloads and orchestration.
• Infrastructure as Code experience with tools such as Bicep, Terraform, Pulumi, or AWS CDK.
• Strong automated testing and CI/CD experience across full-stack delivery.
• Ability to make significant technical contributions, solve complex engineering problems, and make sound architecture decisions.
• Clear communication with both technical and non-technical stakeholders.

• You are a player-coach: comfortable owning people leadership while remaining an active practitioner.
• You use AI agents to increase engineering throughput, but you keep quality, testing, security, and production decisions under clear human control.
• You bring structure without creating unnecessary process and identify technical dependencies, delivery risks, and quality issues early.
• You are comfortable working in a small-team environment where priorities can shift and where leadership means doing the work as well as directing it.
• You balance modernization with stability and understand that business-critical systems must continue to perform while the architecture evolves.

• Bachelor's degree in Accounting, Finance, Information Systems, Economics, Computer Science, Engineering, or a related field is required.
• Exposure to financial services, accounting, finance, tax technology, finance transformation, tax software development, or implementation environments.
• Ability to take ownership of assigned work through completion, including requirements, configuration, testing, debugging, and system/process changes.

• Relevant professional certifications or advanced degrees - such as CPA, EA, JD, or a master's degree in business administration, finance, economics, computer science, information systems, engineering, quantitative economics, or a related field - are a plus, but not required.
• Familiarity with GitHub, GitHub Actions, Atlassian tools, SonarQube, Mend, Aqua Trivy, and WIZ.
• Experience with micro front-end architectures.
• Experience modernizing mixed legacy/new technology environments while continuing to ship.
• Experience building practical engineering guardrails for AI-assisted or agentic development.

• The team ships predictably while maintaining strong quality, testing, security, and release discipline.
• The Engineering Manager remains technically credible and materially contributes to delivery rather than operating only as a coordinator.
• Legacy components remain stable while modernization progresses in deliberate, low-risk increments.
• AI agents are used productively with clear verification, human review, and production controls.
• Engineers receive timely technical feedback, coaching, and clear expectations, and the team's technical hiring bar remains high.
• Operational support improves through better automation, runbooks, documentation, and reduced manual toil.

At FormativGroup, you'll work with people who are practical, collabroative, and focused on solving meaningful business and technology problems. We're growing, which means you'll have opportunities to contribute ideas, work closely with experienced leaders, and help shape how we deliver for our clients.

Applicants must be authorized to work for ANY employer in the U.S. We are unable to sponsor or take over sponsorship of an employment visa currently.

To be considered for this position, candidates must reside in one of the following U.S. states: AL, AR, AZ, CA, CO, CT, DE, FL, GA, IA, ID, IL, IN, KS, MA, MD, MI, MN, MO, NC, NH, NJ, NV, NY, OH, OK, OR, PA, TN, TX, VA, WI, and Washington DC. Candidates residing outside these states are not eligible for consideration currently.