Staff Backend Engineer (Remote, Canada)

Our Story:

Short Story is an award winning, technology-powered retailer dedicated to petite women 5'4" and under. Our mission is to create a seamless shopping experience for millions of petite women so they can dress with effortless confidence.

As a fast-growing startup, we're revolutionizing retail with a data-driven learning system that leverages customer feedback to create tailored products. We've been recognized by top publications like Forbes, Fortune and are backed by top investors who share our vision of building the world's next great consumer brand.

Our Values:

We're building a company with intention and purpose. Our culture thrives on data insights, exceptional commitment to fit, and the urgency to move quickly on what matters.

• ✨ Transform Lives. We're customer-first. Everything we create exists to give her confidence.

• ⚡️ Demand Excellence. We deliver only our best work, in Fit and Finish. We obsess about details others overlook.

• 💪 Embrace Challenges. We see obstacles as opportunities to invent better solutions.

• 💡 Think Differently. We get a thrill from finding better solutions others haven't seen.

Short Story is a wardrobe-as-a-service that connects petite women with clothing that actually fits. Behind the scenes, our tools enable stylists to deliver personalized recommendations, while our logistics and warehouse stacks ensure fast, seamless order handling. With a mix of internal and customer-facing platforms, we’re building thoughtful, elegant systems to power our growth—and that’s where you come in.

The Role:

As one of the first 5 engineers, this is a high-impact opportunity to shape the backbone of Short Story’s tech ecosystem. Reporting to the Head of Engineering, you’ll work across internal and customer-facing platforms—powering everything from order processing to warehouse ops and customer personalization.

You’ll be part of a lean but mighty engineering team, collaborating closely with product managers, operators, and front-end engineers. You'll also set foundational backend patterns, influence architectural decisions, and help us scale with speed and intention.

• Design, build, and maintain scalable backend services in Python (Flask, Falcon, or FastAPI)

• Write clean, well-documented, and well-tested code using Pytest and modern API patterns

• Collaborate with cross-functional teams to implement robust order and customer handling systems

• Own core infrastructure components across AWS, Postgres, and Kubernetes

• Deploy and monitor services using CI/CD best practices and observability tools

• Contribute to system architecture and play a key role in tech design decisions

• Ensure reliability and performance across systems that handle logistics, personalization, and customer interactions

• Help establish engineering guidelines and backend best practices

• (Bonus points if you love games like Factorio—our ops team is basically a logistics simulator IRL)

Must Haves:

• You have back-end development experience and have built and scaled complex systems end-to-end

• You’re fluent in Python and have shipped production systems using frameworks like Flask, Falcon, and/or FastAPI

• You’ve worked with containerized services in Kubernetes and are confident deploying to cloud platforms like AWS

• You have strong experience with relational databases like Postgres and know how to write efficient, scalable SQL

• You’ve led backend architecture decisions and can identify when to optimize, refactor, or replatform

• You’re experienced with CI/CD pipelines, monitoring, and observability tools to keep systems healthy

• You’ve built and maintained robust test suites using Pytest (or similar frameworks) and care about reliability

• You’ve designed APIs that are clean, consistent, and built to last

• You know your way around queue-based or event-driven architectures and can design systems for scale

• You’re thoughtful about documentation, communication, and mentoring others

• You thrive in fast-paced, ambiguous environments and enjoy owning complex problems from idea to execution

• You’re excited by ambiguity and love solving complex problems from end to end

Nice to Haves:

• 5+ years of experience in professional back-end development

• Experience working in a fast-moving startup environment

• Experience integrating/building component systems and libraries for large codebases

• Have worked on sprint-based teams

• Have experience working remotely with timezone differences

• Have led or built a back-end engineering team before

• Have contributed to open-source or have a strong portfolio of personal project

Benefits and Compensation:

• 4 weeks vacation (20 days)

• Medical & dental benefits

• Fully remote work with optional office access in San Francisco and Toronto

• Ownership and autonomy in a fast-growing, mission-driven company

Short Story is committed to providing equal employment opportunity and a work environment free of discrimination and harassment for all employees and applicants. We work diligently to ensure equal opportunity for all applicants and employees without regard to race, color, religion, sex, sexual orientation, gender identity, national origin, disability, age, Veteran status, or other legally protected characteristics.