Senior Software Engineer, Back-End (Remote Canada)

About Short Story: Short Story is an award-winning, technology-powered retailer dedicated to serving millions of underserved petite women 5’4” and under. As a fast-growing, Y-Combinator backed startup, we are completely revolutionizing retail with a proprietary, data-driven learning system that leverages custom customer feedback models to engineer perfectly tailored products. Backed by premier institutional venture funds and featured across major business publications like Forbes and Fortune, our elite team of hackers is dedicated to reinventing the fashion supply chain so women can dress with total, effortless confidence.

Position Overview

What happens when your proprietary business model completely breaks the rigid assumptions most monolithic e-commerce platforms were built on? You step up and build your own from scratch. At Short Story, we are completely rethinking the entire retail software layer—spanning complex automated inventory pipelines, multi-tier warehouse logistics automation, data platform scaling, and granular personalization matching algorithms. We are seeking a high-agency Senior Backend Engineer to design and implement robust, clean systems from first principles, taking deep technical ownership over problems that do not have obvious textbook answers.

Key Responsibilities

• Backend Services Engineering: Design, implement, and optimize scalable, highly concurrent backend microservices to power our core business logic and internal operations workflows.
• End-to-End Feature Ownership: Lead projects through the full software engineering lifecycle—taking abstract requirements from early data modeling and architectural specs through to production release and iterations.
• API & Database Orchestration: Construct clean, stable, and extensively documented RESTful or internal communication APIs while designing relational schema variations inside **PostgreSQL**.
• Cross-System Optimization: Track and manage interconnected system dependencies across core transactional order fulfillment pipelines, automated inventory counts, and data warehouse ingestion layers.
• System Stability & Observability: Harden ecosystem reliability by implementing telemetry tracking alerts, comprehensive monitoring dashboards, and robust error isolation handling.
• Engineering Governance: Elevate baseline development execution standards through constructive, meticulous code reviews, pair-programming sessions, and clear architecture documentation updates.

Required Skills & Qualifications

• 5+ years of verified professional experience in software engineering and production systems architecture, with at least 2+ years of dedicated experience writing scalable backend layers in Python.
• Expert-level command over fundamental computer science data structures, low-latency algorithms, and operational database normalization methodologies.
• Demonstrated experience developing with a modern Python web framework (such as Django, FastAPI, or Flask) alongside standard software testing frameworks.
• Hands-on operational understanding of containerized application management infrastructures utilizing Docker.
• Strong relational database modeling and analytical query performance tuning fluency using SQL and Postgres.
• Proven background delivering stable, highly reliable web APIs paired with excellent documentation and clean-code design practices.
• Location Context: 100% remote-first workspace infrastructure support open to qualified software developers based anywhere within Canada.

Preferred Strategic Indicators (Nice to Have)

• Direct production background utilizing Test-Driven Development (TDD) principles to engineer fault-tolerant business software.
• Prior technical leadership experience acting as a Tech Lead or Architecture Owner for an engineering group of 3+ developers.
• Proven tracking history deploying or scaling large-scale distributed systems or event-driven microservices architectures.
• Familiarity navigating continuous integration and continuous deployment (CI/CD) pipelines, multi-stage release cycles, and sprint-based agile tracking methods.

What We Offer

• The exceptional professional canvas to write custom proprietary e-commerce and logistics systems from scratch for a hyper-growth, Y-Combinator backed tech scale-up.
• Highly competitive compensation package calibrated accurately based on your Python backend mastery and technical evaluation metrics.
• Generous Paid Time Off (PTO) structures allowing you to systematically unplug and recharge.
• Comprehensive health, vision, and dental insurance benefit plans to take care of you and your family.
• Lucrative employee discounts on all corporate merchandise and apparel.
• A fast-moving, high-trust engineering culture of smart, passionate builders driven by high autonomy and zero bureaucratic friction.