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Senior Director, Technology

Foxtrot

Foxtrot

IT, Sales & Business Development
Chicago, IL, USA
Posted on Dec 5, 2025
Description

About Foxtrot:

Foxtrot is reimagining the café—a place where great food, genuine hospitality, and joyful experiences come together. Everything we do is rooted in our values: being thoughtful shopkeepers and gracious hosts, leading with taste and creating the future, and sharing joy in every interaction.

As we grow, we are strengthening the systems, tools, and support that help our teams shine. Adaptability, curiosity, and continuous learning are at the heart of how we build and evolve. We’re committed to creating an environment where our people feel empowered to experiment, innovate, and create the future of the Foxtrot café experience.

We’re seeking a Senior Director of Technology who is passionate about community, energized by solving complex challenges, and excited to build a more connected, joyful café experience through impactful technology and leadership.

About the role:

Foxtrot is looking for a Senior Director of Technology to lead the next chapter of our technical evolution. This role is ideal for a hands-on technical leader who can balance coding, architecture, and infrastructure with strong stakeholder communication and strategic decision making. You will oversee our engineering roadmap, guide technical execution, manage vendors and partners, and build systems that support a growing, modern retail business. The ideal candidate enjoys switching between writing production code, shaping long-term technology strategy, and partnering with leaders across the company.

Responsibilities:

  • Lead Foxtrot’s overall technology strategy across backend services, mobile apps, infrastructure, data, and our retail locations.
  • Write high quality production code in Python, PHP, and related frameworks while guiding engineering standards and best practices
  • Build and maintain Foxtrot’s BI and reporting capabilities, ensuring accurate data models, dashboards, and insights that support decision making across the business
  • Oversee the architecture and reliability of core systems including MySQL databases, AWS infrastructure, and mobile applications
  • Manage technical vendors, development partners, and third party platforms to ensure quality, accountability, and performance
  • Collaborate with leaders across operations, merchandising, marketing, and finance to prioritize requests and align the roadmap with company goals
  • Drive execution of complex cross functional projects from scoping through delivery
  • Implement strong security, scalability, and observability practices to support growth
Requirements
  • 6 to 10 years of engineering experience, including time spent in a fast paced startup or high growth environment
  • Strong proficiency with Python and PHP, as well as modern API design and backend frameworks
  • Hands-on experience with AWS services including EC2, RDS or Aurora, ECS or Fargate, S3, and networking fundamentals
  • Solid MySQL knowledge including schema design, query optimization, and data modeling
  • Experience working with iOS, Android, or React Native
  • Demonstrated ability to communicate technical concepts to stakeholders in product, operations, and leadership
  • Experience managing external engineering vendors or external development resources
  • Strong project management skills with an ability to manage competing priorities
  • A mindset focused on ownership, problem solving, and continuous improvement