(Remote) DevOps Team Lead

Chicago, IL (Remote)
Des Plaines, IL 60018, USA

Description

Who we are

Fidelity Life is a leading provider of financial security for middle market consumers. With a history of innovation, the company is redefining the life insurance industry with patented products and processes. Fidelity Life pioneered the use of predictive analytics to streamline the new business process and revolutionize the speed that policies can be issued. Established in 1896, Fidelity Life enjoys a long track-record of success and continues to build its reputation of sound fiscal management and customer-focused innovation.

In concert with Fidelity Life, eFinancial is an online and call-center-based insurance agency with a proven direct-to-consumer life insurance model. Using a proprietary and patented sales technology platform, eFinancial’s licensed agents help thousands of consumers each day with their unique life insurance needs – often with just a single phone call. To complement this channel, the company recently expanded to offer an entirely digital purchase experience.

Fidelity Life and eFinancial are part ofiA Financial Group and are revolutionizing the life insurance industry to make protection more accessible and affordable for everyday Americans. With integrated marketing, product manufacturing, and controlled distribution, the enterprise is uniquely positioned to grow.

Key Responsibilities

• Lead the design, implementation, and ongoing management of scalable AWS cloud infrastructure, including the team’s most complex technical initiatives, while coaching engineers through successful delivery.


• Build and maintain CI/CD pipelines (Bitbucket Pipelines), Terraform infrastructure as code, and internal platform tooling.


• Accountable for the successful execution of complex production deployments while coaching engineers and ensuring repeatable automation.


• Improve deployment safety through automation, pre/post-deploy verification, and rollback.


• Establish the team's technical implementation strategy and continuous improvement roadmap in alignment with enterprise architecture, platform standards, and organizational objectives. Drive enterprise ecosystem improvements through hands‑on technical leadership.


• Implement and continuously improve the team's production ownership model in alignment with organizational operational standards.


• Deliver team commitments while supporting organizational operational objectives established by the Director.


• Serve as people leader for the team's engineers, including performance management and goal setting, ongoing feedback, career development, and hiring participation; set and enforce the team's quality standards and review practices.


• Communicate with leadership and across teams, translating both ways; author and present the team's technical documentation and direction.


• Enforce enterprise standards, security best practices, and compliance, including the Environment Management agreement and the change and incident/PIR processes.


• Design, build, and continuously improve the shared engineering platform that enables product teams through automation, IaC, CI/CD, developer tooling self‑service capabilities.


• Evaluate, implement, and promote AI‑enabled engineering and operational automation that improves developer productivity, deployment quality, incident response, and platform operations.

Qualifications:

• B.S. in Computer Engineering or related field, or commensurate real‑world DevOps experience.


• 7+ years in a DevOps role, cloud infrastructure, or platform engineering experience, including demonstrated experience leading engineers, owning technical delivery, or managing complex cross‑functional technical initiatives.


• Proven experience with AWS services and cloud migration projects.


• Extensive experience with CI/CD tools and modern pipeline automation; experience with Bitbucket Pipelines preferred.


• Proficiency in Terraform for infrastructure as code.


• Strong knowledge of Atlassian products (JIRA, Confluence, Bitbucket).


• Solid understanding of containerization and orchestration tools (e.g., Docker, Kubernetes).


• Demonstrated experience leading incident response, owning production reliability, mentoring engineers, and setting team technical standards.

Skills:

• Excellent problem‑solving and analytical skills.


• Strong communication and collaboration abilities; writes clear documentation and presents technical direction.


• Sound judgment, weighing decisions at the organizational level for cross‑team impact.


• Self‑directed and able to lead unfamiliar or ambiguous technical initiatives with minimal supervision while keeping stakeholders informed and aligned.


• Willing to learn and adapt to new technologies, leading by example.

Licenses + Certifications:

• AWS Certified DevOps Engineer Professional (preferred)


• AWS Certified Security Specialty (optional)


• AWS CloudOps Administrator Associate

We believe in taking care of our employees and their families. We offer a comprehensive benefits package designed to support your health, well‑being, and financial future. Here’s a look at what we provide:

• Medical Insurance: Choose from a variety of plans to fit your healthcare needs.


• Employer-Paid Vision : Comprehensive eye care coverage at no cost to you.


• Employer-Paid Basic Life and AD&D Insurance: Peace of mind and additional protection.


• Employer-Paid Short‑Term and Long‑Term Disability Insurance: Financial support in case of illness or injury.


• 401(k) Plan: Save for your future with a company match to help you grow your retirement savings.


• PTO and Sick Time accrue each pay period: Take time off when you need it


• Annual Bonus Program: Performance‑based bonus to reward your hard work.

EEOC/Other: eFinancial/Fidelity Life Association is an equal opportunity employer and supports a diverse workplace. As an eFinancial/Fidelity Life employee, you will be eligible for Medical and Dental Insurance, Health Savings Accounts, Flexible Spending Accounts (Health, Dependent Care & Transit), Vision Care, 401(K), Short‑term and Long‑term Disability, Life and AD&D coverages.

Remote work is not available in the following States:

California, Colorado, Connecticut, and New York.

Qualifications

Licenses & Certifications

Required

Preferred

Equal Opportunity Employer
This employer is required to notify all applicants of their rights pursuant to federal employment laws.For further information, please review the Know Your Rights notice from the Department of Labor.