Remote Senior Software Engineer, Back-End (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.

What happens when your business model breaks the assumptions most e-commerce platforms were built on?

You build your own.

At Short Story, we’re rethinking how online shopping works: from inventory and logistics to personalization and fit, because the standard playbook doesn’t work for our customers. That means building systems that don’t fit neatly into existing patterns.

If you’re excited by designing systems from first principles and working on problems without obvious answers, you’ll feel at home here.

About the Team

You’ll be part of a fast-moving engineering team building the systems that power our customer experience, warehouse operations, and data platform. We value engineers who take ownership, move quickly, and are comfortable figuring things out as they go.

The Role

As a Senior Backend Engineer, you’ll design and build the services that power our core workflows, from order processing to logistics and internal operations.

You’ll own meaningful parts of the system end-to-end, making decisions about data models, APIs, and system behavior. You’ll work closely with product, frontend, and operations to ensure what we build is reliable, scalable, and actually solves the problem.

What You’ll Do

• Design, build, and maintain backend services that power core business workflows

• Own projects end-to-end, from early design through production and iteration

• Design APIs and data models that are clear, stable, and easy to work with

• Work across systems (orders, inventory, logistics, data) to solve complex, interconnected problems

• Make thoughtful tradeoffs between speed, scalability, and maintainability

• Improve system reliability through monitoring, testing, and debugging

• Contribute to engineering standards, code reviews, and documentation

Must Haves:

• 5+ years of software development experience, 2+ Years of Python experience

• 5+ years of experience with data structures and algorithms

• Familiar with infrastructure, monitoring, and CI/CD practices

• Familiar with the following technologies:

  • A Python web framework

  • Testing frameworks

  • Containerized workloads (Docker)

  • Relational database (Postgres preferred) and SQL

• Focus on communication and documentation

• Experience designing stable, scalable, and well-documented APIs

Preferred qualifications:

• Test-driven development (TDD) experience

• Tech Lead for an engineering team of 3+ people

• Proven track record running large-scale distributed systems

• Worked in sprint-based environments

Compensation & Benefits:

• Generous Paid Time Off

• Comprehensive health, vision, and dental care

• 401k with company match (US)

• Either in-person in San Francisco, or remote in US or Canada

• Employee discount on merchandise

• Opportunity to work at a Y-Combinator backed startup with a dedicated and experienced founding team

Why You'll Love Working at Short Story:

• You'll get to work at an early stage start-up, to build the culture, and to have an outsized impact on our company

• You'll get the opportunity to try your hand at new things; we deeply believe in giving people opportunity to venture into new areas

• We are a successful, fast-growing startup solving problems that have not been solved before and reinventing fashion for an underserved segment

• We are a group of smart, passionate hackers with a wealth of diverse experiences

• We are motivated by unique challenges and opportunities

• We are driven by the mission of helping petite women find their perfect fit so they can dress with total confidence

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.