Day Remote Flask Developer Jobs in Chicago, IL (NOW HIRING)

About Attain

Built for consumers and companies, alike

Klover’s engineering team powers one of the fastest-growing fintech platforms in the U.S., supporting over one million active users each month. Our systems process and move more than $1.5 billion annually, enabling real-time access to financial tools, rewards, and services that help people improve their day-to-day lives.

As part of this team, you’ll help design, build, and scale the systems that underpin Klover’s core products and platform. You’ll work on high-impact, production-grade systems that prioritize reliability, security, and performance, and that integrate with a broad ecosystem of internal and external services. The work you do will directly shape how users interact with Klover’s products, access their money, and experience transparent, low-fee financial services.

Klover engineers collaborate closely with colleagues across backend, frontend, data science, and product teams to deliver scalable, high-quality solutions for a rapidly growing user base. You’ll have the opportunity to work with modern technologies and architectures while helping define and evolve the next generation of inclusive, data-powered financial products—building systems and interfaces that emphasize reliability, privacy, and performance at scale.

Attain Office Hybrid Schedule (where applicable): 

• Chicago, IL & New York, NY: 4 days in-office; 1 day remote
• We are also potentially open to discussing a remote arrangement for the right candidate

As a Senior/Staff Site Reliability Engineer, you will play a critical role in building out and maintaining the infrastructure that powers all of our systems, as well as all of the supporting tools to ensure that those systems are running smoothly. Automation is the core of this role. We expect you to hunt down manual toil wherever it hides and engineer it out of existence — and to do that with the best tooling available, including AI agents you direct to write, test, and ship infrastructure code.

We treat fluency with modern AI as a first-class SRE skill, along with cloud platform literacy, a strong dedication to observability, and a laser-focus on improving developer experience. You will work closely with nearly every engineering team at Attain, helping to ensure that our systems are operating at peak efficiency, and preparing us to handle the scale of our future growth.

• Use AI agents as a force multiplier for yourself and others
• Create, improve, and maintain internal agentic tools and harnesses
• Add automation to both existing and new systems until manual processes, and the toil that comes with them, simply go away
• Write Terraform modules for deploying infrastructure resources via our GitLab pipelines
• Develop Helm charts for deploying services and jobs in our Kubernetes cluster
• Define metrics, network policies, and routing rules for our Istio service mesh
• Monitor and maintain our GCP BigQuery, Spanner, and CloudSQL databases
• Pipe metrics to our Google-managed Prometheus instance and build out Grafana dashboards and alerts to increase visibility on our systems
• Experiment with GCP offerings, 3rd party vendors, AI tooling, and open-source projects to further automate and secure day-to-day operations
• Pair with engineering leads to instrument and monitor critical functionality
• Participate in architecture design and capacity planning discussions to ensure that our systems are scalable, maintainable, reliable, and secure
• Build, maintain, and improve our CI/CD pipeline

• You reach for automation before you reach for a runbook, and a manual process is something you want to delete, not document
• You treat AI agents as power tools and have real opinions about how to drive them — especially when to stop trusting them
• You are comfortable wearing many hats
• You have a willingness to learn and teach in a fast-paced, collaborative environment
• You have a strong desire to automate things
• You readily provide constructive feedback, and also proactively seek feedback to improve yourself
• You like to get your hands dirty and tinker with/stress test new technologies

• 6+ years of experience building and maintaining large-scale cloud-native infrastructure (AWS and/or GCP)
• Demonstrated fluency directing AI coding agents (e.g. Claude Code, Cursor, or similar) to build, operate, and debug real infrastructure; and robust and experienced judgment on verification of their work
• A track record of replacing manual operations with durable automation
• Experience working with the containerization technologies Docker, Kubernetes, and Istio or a similar service mesh technology
• Experience with SQL database technologies such as MySQL, Google BigQuery, and Google Spanner
• Experience with stream technologies such as Kafka and Amazon Kinesis
• Experience with pub sub technologies such as AWS SNS and Google Pub/Sub
• Experience with serverless computing technologies such as AWS Lambda and Google Cloud Functions/Google Cloud Run
• Experience with infrastructure-as-code tools such as Terraform
• Experience with observability tools such as Datadog, Prometheus, and Grafana
• Strong computer science and software engineering fundamentals
• Experience with SOC2 and PCI Compliance processes and requirements

We are excited to hear from you. 

At Attain, we are passionate about finding people to continuously help us grow our organization. We encourage you to apply, even if your experience doesn’t match every detail on the job description. If we don’t see something that immediately fits, we will keep your resume on file for future opportunities.