Principal Software Engineer - AI & Cloud Solutions

About the Role

We’re hiring a Principal Software Engineer remote to join our growing team at commonsku! This role is pivotal in reshaping a $26B industry and building the future of branded merchandise. As a Principal Software Engineer remote, you will help us scale our technical architecture, lead high-impact AI initiatives, and establish the technical vision that will power our platform for years to come.

What You’ll Do

• Lead Technical Strategy: Drive the design and delivery of complex, cross-team initiatives by breaking down ambiguity into executable milestones.
• Champion AI Innovation: Partner with our Senior AI Engineer and Product Management teams to provide technical leadership, design, and development for critical AI projects.
• Drive AI Integration: Lead the seamless integration of LLMs and generative AI technologies into user-friendly features that solve real customer problems.
• Set the Standard: Define and evolve technical patterns, standards, and best practices that improve system reliability and maintainability across the entire engineering organization.
• Build & Mentor: Contribute hands-on code where it provides the most leverage while mentoring senior engineers to sharpen their judgment, design quality, and decision-making capabilities.
• Ensure System Health: Lead root cause analysis for significant incidents and drive measurable improvements in system performance and observability.
• Anticipate & Mitigate: Plan with a 12–18 month horizon to identify technical risks early, driving mitigation before issues become incidents or delays.
• Communicate & Align: Clearly communicate technical decisions, tradeoffs, and learnings broadly, aligning diverse technical and non-technical audiences around a shared direction.

Requirements

• Extensive Technical Leadership: 10+ years of experience building and operating complex SaaS systems, with a proven track record of leading major initiatives with real accountability.
• Full-Stack Proficiency: Deep experience with Python (specifically production systems using frameworks like FastAPI), PHP, React, and relational databases (MySQL).
• Cloud & Infrastructure Expertise: Proficiency in cloud platforms (AWS, GCP, or Azure) and modern CI/CD practices (GitHub Actions, CircleCI).
• AI Implementation: Hands-on experience building agentic systems, complex workflows, and integrations with third-party LLMs (OpenAI, Gemini).
• System Design Judgment: A strong ability to balance speed, quality, and long-term sustainability with immediate business needs.
• Influence Without Authority: Demonstrated ability to mentor senior and junior peers and lead cross-functional teams toward a shared technical vision.
• Operational Excellence: Familiarity with monitoring and observability tools (e.g., Datadog, Rootly) and a commitment to maintaining high-performing, reliable systems.
• Comfort in Ambiguity: You thrive when shaping clarity where none exists and are comfortable working independently and asynchronously.

Nice to Have

• Experience leveraging Generative AI Code Assistants to accelerate development and stay ahead of emerging AI capabilities.

What We Offer

• Starting salary for this role is $180,000–$200,000, depending on previous experience and skillset, plus a 10% annual bonus opportunity based on company performance.
• Remote-first culture with excellent in-person experiences sprinkled in.
• Company-wide closure between December 25th and January 1st.
• Health and dental benefits, including a $1,000 healthcare spending account.
• RRSP/TFSA contributions up to $3,000 a year (no employee contribution required!).
• Twice-yearly company-wide summits.
• A delightful team of smart people who are good at what they do.