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Hirewell

Senior Director of Technology

Hirewell, Chicago

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Base pay range

$170,000.00/yr - $210,000.00/yr

Additional compensation types

Annual Bonus

Our Partner is a rapidly growing, modern retail client, searching for a Senior Director of Technology . This is a pivotal leadership role for an individual ready to spearhead the next phase of the client’s technical development reporting directly into the CEO.

About the Role

This unique leadership position requires a true "hands‑on" Technical Architect and Strategist with a deep foundation in software development. The ideal candidate must have a proven track record of growing their career from a Software Engineer into a strategic leadership role (with hands‑on coding expected).

This leader will be the single point of ownership for the entire organization’s technology strategy and execution—a true "jack of all trades" who knows how to leverage expertise. The role involves managing the technology landscape end-to-end, primarily by effectively directing and collaborating with MSPs and external vendors to scale and support the infrastructure and operational needs.

The ideal candidate for this role is an expert technical leader who can expertly balance architectural design and strategic decision-making while maintaining the ability to dive into day-to-day coding (as needed) to troubleshoot, prototype, or set standards.

This leader will guide the overall engineering roadmap, ensure technical execution excellence, and build scalable systems to support the growth of the retail business. Our client is looking for someone who enjoys seamlessly transitioning between defining long‑term technology strategy, occasionally writing production-level code, and collaborating with cross‑functional leaders.

Key Responsibilities

  • Develop and drive the overarching technology strategy.
  • Set best practices and engineering standards while actively contributing high‑quality production code, primarily in Python and PHP.
  • Establish robust Business Intelligence (BI) capabilities, including data models, reporting dashboards, and actionable insights for business decision‑making.
  • Manage the architecture, reliability, and security of core systems, including cloud infrastructure (AWS) and database management (MySQL).
  • Oversee technical vendor, development partner, and third‑party platform relationships to ensure accountability and performance.
  • Partner with leaders in operations, finance, and other business units to align the technology roadmap with strategic company objectives.
  • Lead the successful execution of complex, cross‑functional projects from initial scoping through final delivery.

Qualifications and Experience

  • 6 to 10 years of professional engineering experience, including time spent in a rapid‑growth or fast‑paced startup environment.
  • Deep expertise in Python and PHP and experience with modern API design and backend frameworks.
  • Strong hands‑on experience with core AWS services, such as EC2, RDS or Aurora, ECS or Fargate, S3, and foundational networking knowledge.
  • Solid knowledge of MySQL, including effective schema design, query optimization, and data modeling.
  • Familiarity with mobile platforms (iOS, Android, or React Native) is a plus.
  • Demonstrated ability to clearly articulate complex technical concepts to non‑technical stakeholders across product, operations, and executive leadership.
  • Proven experience managing external engineering resources or development partners.
  • Excellent project management abilities, with a skill for navigating and prioritizing competing demands.

Seniority Level

Executive

Employment Type

Full‑time

Job Function

Information Technology, Management, and Engineering

Benefits

  • Medical insurance
  • Vision insurance
  • 401(k)

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