Principal Software Engineer

🌟 Ready to help reshape a $26B industry and build the future of branded merch?

commonsku is revolutionizing the promotional products industry. Our platform empowers branded merch distributors to work smarter — managing projects, building quotes, placing orders, and collaborating with clients and suppliers seamlessly through the power of the Connected Workflow.

We’re a remote‑first, community‑driven team obsessed with elevating our customers, their clients, and the broader industry. Our values – Community First, Ten Steps Ahead, Fast Forward, and Delightful Work – guide us. We believe you can innovate, push forward, and do more, while also sharing a laugh, supporting your colleagues, and having a life outside of work.

If you’re energized by ambitious work, creative collaboration, and helping to build something great, you’ll want to keep reading.

Principal Software Engineer – Engineering

In this role, you’ll 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. As a senior individual contributor, you’ll lead large, cross‑team initiatives, contribute to a high‑trust environment, and play a direct role in shaping the future of the industry. You’ll remain hands‑on where it matters most while raising the technical bar across the entire organization.

• A community mindset — You see customers as partners and coworkers as collaborators. You lift others up, always follow through on your commitments, and thrive in a team that does the same. (Community First)
• Momentum and ownership — You act with optimism, take initiative, and turn ideas into results. You move fast and bring others with you. (Fast Forward)
• Vision and boldness — You don’t just react — you anticipate. You think big, challenge the status quo, and push the work (and the industry) forward. (Ten Steps Ahead)
• Joy in the craft — You care deeply about what you build and how it makes people feel. You bring thoughtfulness, transparency, and a sparkling sense of humour to the table. (Delightful Work)

• Lead Technical Strategy:
  Drive the design and delivery of complex, cross‑team initiatives by breaking down ambiguity into executable milestones. Connect architectural decisions directly to business goals, customer impact, and product strategy.
• 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, trade‑offs, and learnings broadly, aligning diverse technical and non‑technical audiences around a shared direction.

• 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 (Git Hub Actions, Circle
  
  CI).
• AI Implementation:
  Hands‑on experience building agentic systems, complex workflows, and integrations with third‑party LLMs (OpenAI, Gemini).
• System…