Director, Data (Hybrid)

Job Overview

The Head of Data is the senior leader accountable for Rewards Network's data strategy and the organization that delivers it, with end-to-end ownership of the Data Engineering and Data Science functions.

Reporting to the CTO, this director-level role sets the vision for how data creates business value, builds the platform and team to realize it, and serves as the company's primary authority on data architecture, governance, and advanced analytics.

The function is mid-migration to a modern data stack, and this leader will bring disciplined execution, architectural clarity, and consistency while scaling the organization for long-term growth.

The right person is a hands-on player-coach - equally comfortable setting strategy with the executive team and rolling up their sleeves on architecture, code, and models - who can build and scale a high-performing organization as we invest in data as a core pillar of our long-term competitive advantage. Early priorities include assessing the current in-flight build, making deliberate decisions about what to keep and what to replace, and establishing a multi-year data roadmap.

This is a hybrid position that requires in office presence 3 days a week (Tuesday-Thursday) in Chicago.

What you'll bring to the table: (Responsibilities)

• Define and own the data strategy and multi-year roadmap for Data Engineering and Data Science, aligning investments with company objectives in partnership with the CTO and executive team.
• Establish and enforce architecture standards that ensure consistent designs that produce repeatable results.
• Assess the current state of our data infrastructure - evaluate what needs refactoring, and what should be replaced - then execute on that plan with the team.
• Lead the continued build-out of the modern data stack, including ELT pipelines, stream ingestion, transformation logic along with storage and compute - remaining hands-on in design and implementation while serving as the final technical authority on data platform decisions.
• Hire and develop data talent, grow the team with experienced engineers and scientists and develop the existing team members through mentorship, code review, and technical leadership.
• Own data governance, including the data model RFC process - reviewing proposed changes, enforcing boundary discipline, and ensuring no undocumented changes promote to canonical layers.
• Own data pipeline monitoring and observability, ensuring production pipelines have appropriate alerting, data quality checks, and incident response processes so failures are caught early and resolved quickly.
• Own the data function's budget, including headcount planning, platform and cloud spend, and vendor selection and management.
• Serve as the data leader to the executive team and cross-functional stakeholders - reporting on progress, ROI, architectural decisions, and risks, and communicating tradeoffs clearly when business commitments are at risk.

Do you have the right mix of ingredients: (Requirements)

• Bachelor's degree in Computer Science, Engineering, or related field (or equivalent experience)
• 10+ years of experience across data engineering, data science, or analytics, with a strong hands-on data engineering foundation
• 4+ years leading data teams, including direct management of both data engineers and data scientists
• Proven experience leading data science work through the full ML model lifecycle, including MLOps and production deployment
• Strategic leader who can define a data vision, build an executive-ready roadmap, and tie data investments to measurable business outcomes
• Expertise in data engineering - including model design, testing strategy, incremental patterns, and layer boundary governance
• Experience designing and enforcing data modeling standards in a team environment - not just building models, but establishing the patterns others follow
• Demonstrated ability to build, lead, and retain high-performing teams across engineering and science - through hiring, coaching, code review, and setting standards that stick
• Familiarity with CI/CD for data pipelines (GitLab or equivalent) - including automated testing, deployment workflows, and environment promotion strategies
• Experience with data observability and monitoring - alerting on pipeline failures, data quality degradation, and freshness SLAs (familiarity with tools like Elementary, Monte Carlo, or equivalent)
• Strong decision-making under ambiguity - this role requires someone who can move forward with incomplete information and course-correct, not someone who needs consensus to proceed
• Clear, direct communicator with executive presence who can influence senior stakeholders and translate technical tradeoffs into business terms
• Technical expertise in: Python, Apache Airflow, Apache Kafka, cloud data warehouses (Redshift, GBQ, Databricks)

Education, Certifications and Experience: Preferred

• Bachelor's or advanced degree in a technical field
• Experience at a company that has completed a similar legacy-to-modern warehouse migration
• Experience building and scaling a data organization, including managing managers or technical leads
• Experience owning a departmental budget, platform spend, and vendor relationships

Comprehensive benefits package, which includes

• This is a full-time, exempt position. The base salary range for this role in Chicago is $200,000-$250,000 annually, depending on candidate's experience, as well as skills, and other factors. This role is also eligible for an annual bonus target of 20%, bringing total target compensation to $220,000-$300,000.
• Competitive Time Off Benefits: including flexible PTO, 11 company holidays, and parental leave.
• Generous dining reimbursement when you dine with our restaurant clients
• 401(k) plan with a company match
• Two medical plan options- Standard PPO or High Deductible Health Plan (HSA with company match for HDHP participants)
• Partnership with Rx n Go, offering certain prescriptions for free
• Two dental plan options and a vision plan
• Flexible Spending Accounts and a pre-tax commuter benefit program
• Accident, Critical Illness, and Hospital Indemnity Insurance Plans
• Short Term and Long Term disability
• Company-paid life insurance and AD&D insurance, supplemental employee, spouse, and child life insurance
• Employee Life Assistance Program
• Hybrid working environment in a new office space downtown near the Metra Train stations and catered lunches on Tuesdays.

Expected Pay Range $200,000 - $250,000 USD