[Hiring] Director of Engineering @University of Chicago

Role Description

The Bike Shop is seeking a strategic and entrepreneurial technology leader to shape the direction of its software, data, and AI capabilities. As the senior technical leader, you will set the technical vision, guide system architecture, and establish engineering practices across all Shop-built systems. You will lead a dual mandate:

• Delivering production-quality software products that strengthen the Shop’s public technical reputation and serve as essential internal infrastructure.
• Building applied AI and machine learning capabilities.

In this role, you will build and lead the Shop’s engineering function, including:

• Defining the team structure.
• Hiring exceptional talent.
• Establishing technical standards.
• Developing a multi-year technology roadmap.

You will also oversee the technology function’s financial resources, including budgets, forecasts, and project investments. Working closely with research leadership, you will help shape the Shop’s research agenda by identifying what is technically possible and creating the platforms and capabilities needed to support ambitious Center initiatives.

This is a high-impact leadership opportunity for someone who thrives with autonomy and enjoys turning emerging ideas into reliable, real-world systems. Your decisions will influence the Shop’s work across the organization and play a significant role in defining its external technical reputation.

Responsibilities

• Product and Platform Delivery
  • Owns the Shop’s software product portfolio end to end — definition, architecture, implementation, release, and ongoing operation.
  • Drives concept-to-production delivery of externally released applied tools.
  • Owns public release strategy for Shop software, including open-source governance, API design and versioning, packaging, documentation, and support model.
  • Delivers internal platforms, administrative dashboards, and authoring tools that increase research and operational throughput.
  • Owns architecture across a portfolio of concurrent products.
  • Determines when prototypes graduate to production and what hardening is required.
  • Makes build, buy, and adopt decisions and owns vendor and open-source dependency strategy.
• Applied AI/ML Development and Technology Evaluation
  • Leads applied AI/ML engineering aligned to Shop priorities.
  • Translates Shop research objectives into system requirements, architecture, and delivery plans.
  • Identifies where new engineering capability would enable work not currently possible.
  • Prototypes and evaluates emerging AI capabilities.
  • Represents the Shop’s technical work externally.
  • Maintains working knowledge of emerging technologies.
• Technical Direction, Architecture, and Operations
  • Owns end-to-end architecture of the Shop’s cloud platform.
  • Selects the Shop’s core technology stack and defines migration paths.
  • Defines the architecture for the Shop’s AI and agentic systems.
  • Owns model selection and integration decisions for Shop systems.
  • Designs evaluation and monitoring approaches for non-deterministic systems.
  • Sets reliability and performance targets.
  • Designs data ingestion and processing pipelines.
  • Establishes the architecture review process.
• People and Resource Management
  • Establishes and staffs the Shop’s engineering team.
  • Recruits, hires, onboards, and develops technical staff.
  • Manages the financial resources of the Shop’s technology function.
  • Supervises student technical contributors and mentors junior engineers.
  • Serves on the Shop’s senior leadership team.
  • Ensures compliance with institutional, state, and federal policies.
  • Manages employees by establishing annual performance goals.
  • Creates plans to translate business requirements into well-designed applications.
  • Advises decisions on project and infrastructure needs.
  • Performs other related work as needed.

Qualifications

• Minimum requirements include a college or university degree in related field.
• Minimum requirements include knowledge and skills developed through 7+ years of work experience in a related job discipline.

Preferred Qualifications

• 7 years of experience leading technical teams or functions.
• Track record of senior technical leadership at organizations delivering software at scale.
• Experience building an engineering function, including hiring, technical standards, and process definition.
• 10+ years of engineering leadership.
• Experience delivering software-as-a-service and data-as-a-service products.
• Experience owning a technology budget.
• Experience partnering with technical or scientific stakeholders.
• Advanced degree in computer science, engineering, or a quantitative discipline.

Technical Skills or Knowledge

• Production experience with large language model and agentic systems.
• Applied machine learning in production.
• Large-scale data engineering.
• Distributed and real-time systems.
• Cloud infrastructure.
• Data stores.
• Full-stack development across server and client platforms.
• Test and quality engineering.
• Product and design practice.

Preferred Competencies

• Excellent verbal and written communication skills.
• Strong analytical and problem-solving skills.
• Ability to set technical direction under ambiguity.
• Ability to assess technical feasibility of proposed directions.
• Ability to balance rapid prototyping against production reliability.
• Work both independently and as a team member.
• Confidentiality related to sensitive University matters.

Working Conditions

• Remote position.
• Occasional evening or weekend hours.
• Participates in escalation for production services.
• Occasional travel for conferences and collaborator/partner site visits.

Application Documents

• Resume (required)
• Cover Letter (required)

Job Family

• Information Technology

Role Impact

• People Manager

Scheduled Weekly Hours

• 37.5

Drug Test Required

• No

Health Screen Required

• No

Motor Vehicle Record Inquiry Required

• No

Pay Rate Type

• Salary

FLSA Status

• Exempt

Pay Range

• $170,000.00 - $185,000.00

Benefits Eligible

• Yes