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Fantasy

Technology Director

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Remote
Hiring Remotely in USA
Remote
Hiring Remotely in USA

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This role is fully remote. Candidates must be based in the United States or Canada.
 

We are Fantasy.

For over two decades, we've partnered with the likes of Google, Microsoft, Nike, Spotify, and Peacock to build digital products used by billions of people every day. We're now entering our most ambitious chapter: designing and building the next generation of intelligent experiences, where AI isn’t a chatbox but the orchestrator of truly personal products and brand experiences.

 

Your Role.

As a Technology Director at Fantasy, you are part of the technology leadership team and serve as a senior client-facing leader who ensures Fantasy’s technical vision is realized across engagements. You’ll be responsible for leading client relationships, driving solution strategy, and ensuring that Fantasy’s work delivers both creative and technical excellence.

 

This is a hands-on role. At Fantasy, we don’t just direct — we produce. We lead by doing. The Technology Director works closely with engineers, designers, and strategists to prototype, architect, and build alongside their teams. You’ll set the example for quality, innovation, and collaboration, ensuring Fantasy’s technology is as inspiring in execution as it is in concept.

 

You will also play a pivotal role in representing technology externally by owning client partnerships, shaping proposals, scoping opportunities, and contributing to the pre-sales architecture of new business initiatives. Internally, you’ll help shape Fantasy’s technology approach and ensure our craft continues to evolve through collaboration and experimentation.

 

Key Responsibilities.

  • Lead technology strategy and delivery across client engagements, ensuring high-quality execution from discovery through launch.
  • Serve as a trusted technology partner to clients, translating business and creative goals into clear, actionable technical solutions.
  • Partner with design, strategy, and production teams to shape technical direction and ensure technology meaningfully supports the product vision.
  • Contribute hands-on through prototyping, architecture, and production work—leading by example and pushing creative and technical boundaries.
  • Define and evolve technical architectures that balance innovation, scalability, performance, and feasibility.
  • Support pre-sales and scoping efforts by estimating effort, defining technical approaches, and contributing to proposals and client presentations.
  • Evaluate and explore emerging technologies to inspire experimentation, inform future work, and advance Fantasy’s technical practice.
  • Represent the technology practice in workshops, pitches, and project reviews, providing clarity, insight, and strategic guidance.
  • Mentor and collaborate with fellow technologists to promote growth, consistency, and knowledge sharing across teams.
  • Partner with business development and leadership to identify new opportunities and articulate Fantasy’s technology value proposition.

 

Experience and Skills.

  • 10+ years of experience in technology-focused roles, ideally within digital product, innovation, or creative agency environments.
  • Proven experience leading technology strategy and delivery across multiple client or product engagements.
  • Strong background in pre-sales, including scoping, estimation, client collaboration, and proposal development.
  • Demonstrated ability to architect and scope modern web, application, or platform solutions.
  • Broad technical fluency across modern stacks (cloud, APIs, front-end frameworks, data systems), with deep hands-on expertise in either front-end or back-end engineering.
  • Hands-on builder mindset with the ability to contribute directly through prototyping, architecture, and implementation.
  • Clear and confident communicator who bridges technical, business, and creative perspectives.
  • Strong appreciation for design, craft, and high-quality user experiences.
  • Genuine curiosity about emerging technologies, with interest in exploring AI, machine learning, and intelligent systems.

 

Our Commitment

Fantasy has been building diverse, inclusive teams since 1999. We believe the range of perspectives in this building is inseparable from the quality of what we ship. Fantasy is an Equal Opportunity Employer.

What you need to know about the Chicago Tech Scene

With vibrant neighborhoods, great food and more affordable housing than either coast, Chicago might be the most liveable major tech hub. It is the birthplace of modern commodities and futures trading, a national hub for logistics and commerce, and home to the American Medical Association and the American Bar Association. This diverse blend of industry influences has helped Chicago emerge as a major player in verticals like fintech, biotechnology, legal tech, e-commerce and logistics technology. It’s also a major hiring center for tech companies on both coasts.

Key Facts About Chicago Tech

  • Number of Tech Workers: 245,800; 5.2% of overall workforce (2024 CompTIA survey)
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