Independent Contractor Capacity Engineer Jobs in Chicago, IL

Job Title: Director, Data Enablement

About Us:

On a mission to deliver affordable, delightful healthcare for all, First Stop Health provides connected, whole-person virtual care to employers 24/7 through app, website, or phone in all 50 states. First Stop Health prioritizes an engaging and easy-to-use experience, setting people on healthier journeys through care at multiple stages. We are proud to be recognized as one of Fast Company’s Most Innovative Companies.

First Stop Health offers a comprehensive benefits package that includes various health and medical coverage options, dental and vision coverage, disability and life coverage, making healthcare easily accessible. For those that choose to waive medical coverage a monthly medical waiver allowance will be provided.

First Stop Health offers a remote-first work environment and flexible paid time off, including Summer Fridays. Furthermore, the employer match 401k plan and monthly phone stipend demonstrates the company's commitment to employee financial well-being. The First Stop Health membership benefit is another added perk for employees and provides our virtual care solutions -- Urgent Care, Mental Health, and Primary Care -- from their very first day!

Job Description:

We're hiring a Director, Data Enablement to build and lead the operational backbone of our data organization. This is a high-impact leadership role at the intersection of data engineering, governance, AI infrastructure, and stakeholder partnership — sitting inside a healthcare technology company where the integrity and availability of data directly shape clinical and operational outcomes.

You will own the full data product lifecycle from ingestion through consumption — leading our data engineering teams (Bronze/Silver/Gold architecture), our reporting function, and a flexible contractor capacity deployed against our highest-priority data initiatives. You'll partner across the business to enable the data each team needs to do their work and also work in close partnership with our Analytics & Data Science team, serving as the operationalization layer that takes validated insights and graduating experiments and makes them trusted, governed, and permanently available to the business.

This role is for a leader who thinks in systems, earns trust across engineering and business stakeholders alike, and understands that in healthcare, data quality isn't a preference — it’s imperative.

Responsibilities:

Data as a Product

• Own the strategy, roadmap, and execution of our data platform — ensuring data is available, trusted, and AI-ready across all consuming teams (Product, Systems, Security, Client Operations, Analytics)
• Define and maintain data products across our Bronze/Silver/Gold architecture, with clear SLAs, ownership, and quality standards for each layer
• Manage the handoff protocol from Analytics — receiving graduated experiments and models and operationalizing them into production-grade, governed data products
• Partner with IT Systems and Security to ensure data infrastructure is compliant, resilient, and scalable

Governance and Data Quality

• Build and operationalize a data governance framework appropriate for a healthcare technology environment — including data lineage, cataloging, access controls, and quality monitoring
• Own data contracts between producing and consuming teams, establishing clear definitions, quality thresholds, and escalation paths
• Ensure compliance readiness across relevant regulatory frameworks (HIPAA and others applicable to the business)
• Champion a culture where "trusted data" is a non-negotiable standard, not an afterthought

Reporting Excellence

• Oversee internal and customer-facing reporting — ensuring accuracy, timeliness, and diligence across all report outputs
• Partner with each functional area to understand reporting needs and build scalable, governed reporting infrastructure that can grow with the business
• Oversee the reporting products we provide to our customers, ensuring timeliness, accuracy and impact
• Establish review and QA processes that give stakeholders confidence in every number they see

AI and ML Infrastructure Readiness

• Architect and evolve the Gold layer as the primary consumption layer for AI, ML, and product use cases — ensuring data is structured, documented, and ready for model consumption
• Partner with the Analytics team on data requirements for new ML initiatives, building infrastructure ahead of need rather than in reaction to it
• Stay current on the evolving data + AI stack and make informed, pragmatic decisions about tooling and architecture

Team Leadership

• Lead and develop an internal team plus flex contractor capacity (3–4 headcount) deployed across DE and reporting workstreams
• Build the project management and delivery discipline that the engineering team needs to embed effectively in the broader organization
• Create a team culture oriented around reliability, ownership, and continuous improvement
• Develop career paths and growth opportunities that retain strong technical talent

Organizational Influence

• Serve as the primary data infrastructure partner to IT, Product, Client Operations, and Security — proactively understanding their data needs and building ahead of demand
• Translate complex data platform concepts into clear business language for non-technical stakeholders
• Represent the data organization in cross-functional planning, ensuring data implications are considered in every major initiative

Requirements:

• 8–12+ years of experience in data engineering, data platform, or analytics engineering roles, with at least 3–5 years in a people leadership capacity
• Demonstrated experience building or maturing a data governance framework in a production environment
• Track record of operationalizing data products from research or experimental outputs into reliable, governed, production systems
• Experience working with modern data stack tooling (e.g., dbt, Snowflake/Databricks/BigQuery, Airflow or equivalent, data catalog tools)

Leadership and Influence

• Proven ability to embed within and earn trust from business stakeholders — not just manage up and down, but sideways across an organization
• Strong project & product management instincts — able to bring structure and delivery discipline to technically strong but execution-challenged teams

Technical Depth

• Credible enough technically to earn respect from strong data engineers without needing to be the best engineer in the room
• Deep understanding of medallion architecture (Bronze/Silver/Gold) and how each layer serves different consumers
• Familiarity with AI/ML data requirements — feature stores, model monitoring, data versioning, and what "AI-ready" data actually means in practice

Mindset

• Treats data as a product — thinks about consumers, SLAs, reliability, and roadmaps, not just pipelines
• Governance-native — sees rigor as an enabler, not a tax
• Bias toward operationalization — energized by making things permanent, scalable, and trustworthy
• Collaborative by default — understands that the best data organizations win through partnerships, not silos

First Stop Health is committed to diversity, equity, inclusion, and belonging. Research shows that women, people of color and other historically underrepresented groups tend to only apply to jobs in which they meet all the job requirements. Unsure if you check every box? Apply. We would love to consider your unique experiences and how you could make First Stop Health even better.

To learn more about First Stop Health, visit www.fshealth.com and if you require any assistance during the application process or have questions, please don't hesitate to contact our talent acquisition team via email at careers@fshealth.com