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.

🚀 About the Role: Principal Software Engineer

We’re growing — and we’re hiring a Principal Software Engineer to join our Engineering team! 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.

💡 About You

You’re not just looking for a job — you’re looking for a place to do your best work. You bring:

• 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)

🛠️ What You’ll Do

Here’s what you’ll do:

• Lead Technical Strategy: Drive the design and delivery of complex, cross-team initiatives by breaking down ambiguity into executable milestones. You will 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, tradeoffs, and learnings broadly, aligning diverse technical and non-technical audiences around a shared direction.

🔍 What You Bring

Some of the qualities that help you thrive in this role:

• 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.
• A Growth Mindset: You are open to feedback, value diversity of thought, and are constantly looking for ways to elevate the engineering bar.
• Bonus: Experience leveraging Generative AI Code Assistants to accelerate development and stay ahead of emerging AI capabilities.

💰 Compensation & Perks

We believe in fair, transparent compensation. 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.

New hires are expected to come in at the midpoint of this range. However, if this role sounds perfect for you and your expectations are outside of this range, we encourage you to apply and let us know in your application about your ideal package. If we agree that it’s a good fit, we will have open discussion around what’s possible.

Plus:

• Remote-first culture (with plenty of 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 (we call it HQ and you’ll love it)
• A delightful team of smart people who are good at what they do

🌎 Location

This role is open to candidates eligible to work in Canada, with the exception of Quebec (we’re not set up to operate there yet — désolé!).

We’re remote-first, but if you’re based in Toronto, even better. That’s where we were founded and where we maintain our HQ today!

🌱 A Bit More About Us

commonsku supports hundreds of promotional products distributors and suppliers with technology that drive efficiency, growth, and connection. Our skummunity (commonsku + community = skummunity, get it?) is powered by events, education, and shared knowledge and is core to who we are.

We’ve grown by being “for promo by promo” and now, we’re scaling our impact to elevating an entire industry. We’d love your help doing it.

🤖 A Note About AI

We use AI every day at commonsku to be faster and better. If you use AI tools to help you draft your resume or cover letter, that’s totally fine — just make sure what you submit reflects you. We want to hear your authentic voice, not ChatGPT’s.

📬 How To Apply

If this role feels like a fit, apply now at https://commonsku.com/careers!

We try our level best to review and respond to every application we receive. So, once you’ve applied, wait to hear from a member of our People team with an update. If it looks like a good fit, expect a phone interview as the first step.

By the way, you don’t need to meet 100% of the requirements — we value potential, learning, and diversity of thought. Tell us why you're excited, and let’s chat.

❤️ commonsku is an Equal Opportunity Employer

We’re committed to building a diverse team that reflects the skummunity we serve. We welcome applicants of all backgrounds, experiences, and identities.