Virtual Data Assistant Jobs in Chicago, IL (NOW HIRING)

Our Story
At Alight, we believe a company's success starts with its people. Alight embraces values that come directly from our people - purposeful, human, united and growth-minded - reflecting our inclusive culture and promise that our clients expect. We are passionate about connecting purpose with impact. Alight empowers clients to build a healthier and more financially secure workforce by unifying the benefits ecosystem across health, wealth, wellbeing, navigation, and absence management.
Our Benefits
With a comprehensive total rewards package, Alight offers programs and plans that support your mind, body, wallet, and life. Benefits include health, dental and vision coverages starting Day One. Additionally, Alight colleagues enjoy wellbeing programs, retirement plans with contribution matching, generous time off, parental leave, continuing education, and career growth opportunities - all within a thriving global organization.
Flexible Working
So that you can be your best at work and home, we consider flexible working arrangements wherever possible. Alight has been a leader in the flexible workspace and "Top 100 Company for Remote Jobs" 6 years in a row.
Great Place to Work
Thanks to the work of every colleague, Alight has received multiple awards of recognition including "Great Place to Work" for the past 7 years and Fortune's "Best Companies to Work For." To learn more about our company culture and awards Click Here.
We invite you to join our team! Learn more at careers.alight.com.
More than 30 million people rely on Alight for their health, their wealth, and their time away from work. We are building AI that meets them in those moments, agentic assistants that answer real questions and carry out transactions on a participant's behalf, and it runs in production today. The platform this team builds is what makes those experiences fast, reliable, and safe at scale. This is hands-on engineering with a direct line to millions of users, and we are hiring builders at every level to take it further.
We build the AI engineering platform that powers AI delivery across Alight. We own the developer lifecycle, deployment infrastructure, observability, quality automation, document ingestion pipelines, and reusable agent patterns, so delivery teams solve business problems instead of reinventing infrastructure.
Key Responsibilities & What You'll Build

• The agent patterns, retrieval, and guardrails behind the agentic assistants that answer participant questions and carry out transactions on their behalf
• An MCP server that serves a skills registry to AI coding agents right in the IDE
• Reusable agent patterns in LangGraph: multi-agent orchestration, memory, tool-use safety, and guardrails
• An agent evaluation platform (DeepEval, Ragas) with quality gates that block a bad deployment in CI/CD
• Document ingestion and retrieval pipelines: chunking, embedding, vector search, reranking, and citations
• CI/CD and deployment automation for AI agents on AWS (ECS, Fargate, Agent Core)
• AI-enabled devcontainers with tooling, validation, and testing built in
• OpenTelemetry instrumentation, dashboards, and LLM cost and token tracking for production workloads
• Governance controls turned into pipeline checks, with evidence collected automatically
• Semantic caching, rate limiting, and graceful degradation for agent workloads under load
• Reference implementations, SDK and CLI tooling, and the docs other engineers build on

Requirements

• Python. proficiency (3.10+). This is the primary language across the team.
• AWS. Working knowledge of core services (IAM, ECS/Fargate, networking) and comfort in cloud-native environments.
• Software engineering discipline. Version control (Git/GitHub), code review, testing, documentation, and clean code.
• Security awareness. You build things that handle sensitive data, and you think about secrets, permissions, and data protection by default.

Expertise in one of the six:

• AI agent development. LangGraph or similar, multi-agent orchestration, memory, tool use, guardrails, prompt and workflow design.
• Data and retrieval engineering. Chunking, embeddings and vector search, RAG, hybrid search, reranking, retrieval evaluation.
• Quality and evaluation. Agent eval frameworks (DeepEval, Ragas), CI/CD quality gates, groundedness and safety metrics, test automation for AI systems.
• Platform and infrastructure. CI/CD, Terraform, container orchestration on AWS (ECS, Fargate), secrets and IAM, progressive deployment.
• Observability and operations. OpenTelemetry tracing, dashboards and alerting, LLM cost and token tracking, feedback loops.
• Developer experience. MCP servers, devcontainers, CLI and SDK tooling, prompt libraries, the docs and reference implementations others build on.

Application and Interview
By applying for a position with Alight, you understand that, should you be made an offer, it will be contingent on your undergoing and successfully completing a background check consistent with Alight's employment policies. Background checks may include some or all the following based on the nature of the position: SSN/SIN validation, education verification, employment verification, and criminal check, search against global sanctions and government watch lists, credit check, and/or drug test. You will be notified during the hiring process which checks are required by the position.
Alight requires all virtual interviews to be conducted on video. Please be aware that Alight is a camera-on culture and may require occasional travel to one of our physical office locations.
Our commitment to Inclusion
We celebrate differences and believe in fostering an environment where everyone feels valued, respected, and supported. We know that diverse teams are stronger, more innovative, and more successful.
At Alight, we welcome and embrace all individuals, regardless of their background, and are dedicated to creating a culture that enables every employee to thrive. Join us in building a brighter, more inclusive future.
As part of this commitment, Alight will ensure that persons with disabilities are provided reasonable accommodations for the hiring process. If reasonable accommodation is needed, please contact alightcareers@alight.com.
Equal Opportunity Policy Statement
Alight is an Equal Employment Opportunity employer and does not discriminate against anyone based on sex, race, color, religion, creed, national origin, ancestry, age, physical or mental disability, medical condition, pregnancy, marital or domestic partner status, citizenship, military or veteran status, sexual orientation, gender, gender identity or expression, genetic information, or any other legally protected characteristics or conduct covered by federal, state, or local law. In addition, we take affirmative action to employ disabled persons, disabled veterans, and other covered veterans.
Alight provides reasonable accommodations to the known limitations of otherwise qualified employees and applicants for employment with disabilities and sincerely held religious beliefs, practices and observances, unless doing so would result in undue hardship. Applicants for employment may request reasonable accommodations/modifications by contacting their recruiter.
Authorization to work in the Employing Country
Applicants for employment in the country in which they are applying (Employing Country) must have work authorization that does not, now or in the future, require sponsorship of a visa for employment authorization in the Employing Country and with Alight.
Note, this job description does not restrict management's right to assign or reassign duties and responsibilities of this job to other entities; including but not limited to subsidiaries, partners, or purchasers of Alight business units.
#LI-remote
We offer you a competitive total rewards package, continuing education & training, and tremendous potential with a growing worldwide organization.
Salary Pay Range
Minimum :
120,000.00 USD
Maximum :
220,000.00 USD
Pay Transparency Statement: Alight considers a variety of factors in determining whether to extend an offer of employment and in setting the appropriate compensation level, including, but not limited to, a candidate's experience, education, certification/credentials, market data, internal equity, and geography. Alight makes these decisions on an individualized, non-discriminatory basis. Bonus and/or incentive eligibility are determined by role and level. Alight also offers a comprehensive benefits package; for specific details on our benefits package, please visit: Wellbeing and Benefits Selector Page - Alight
DISCLAIMER:
Nothing in this job description restricts management's right to assign or reassign duties and responsibilities of this job to other entities; including but not limited to subsidiaries, partners, or purchasers of Alight business units.
Alight Solutions provides equal employment opportunities (EEO) to all employees and applicants for employment without regard to race, color, religion, creed, sex, sexual orientation, gender identity, national origin, age, disability, genetic information, pregnancy, childbirth or related medical condition, veteran, marital, parental, citizenship, or domestic partner status, or any other status protected by applicable national, federal, state or local law. Alight Solutions is committed to a diverse workforce and is an affirmative action employer.