Executive Assistant at commonsku

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: Executive Assistant

We’re growing — and we’re hiring an Executive Assistant to support our co-founders! In this role, you’ll act as a key partner to the CEO and the President to ensure both founders are able to focus on the highest-priority work by. You’ll enable strategic work from an execution perspective, supporting the logistics and management of the CEO’s top priorities, while driving alignment from the CEO-down, supporting cultural norms, and innovation. The role includes managing schedules, communications, logistics, and related tasks with proactive judgment, discretion, and the ability to anticipate needs in a fast-moving environment. But it’s way more than that too: you’ll collaborate closely with teammates across all of commonsku, contribute to a high-trust and humour-forward environment, and play a direct role in shaping the future of the industry!

The role requires the candidate to be based in Toronto and available for in-person work when needed.

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:

• Act as a force multiplier for the CEO, ensuring their time, attention, and energy are consistently allocated to the highest-impact priorities.
• Apply strong judgment to proactively anticipate needs, risks, and conflicts before they surface, resolving issues independently whenever possible.
• Prepare the CEO for all key interactions by synthesizing context, surfacing relevant insights, and ensuring decisions can be made efficiently.
• Own the execution layer of the CEO’s priorities — translating direction into logistics, follow-through, and closed loops.
• Own end-to-end calendar strategy, not just scheduling: protect focus time, sequence meetings intentionally, and actively manage trade-offs.
• Actively manage access to the CEO, balancing availability with the need for uninterrupted strategic work, with an eye to ensuring the CEO is available and open for all levels of the organization.
• Regularly audit how executive time is being spent and propose improvements to increase effectiveness.
• Serve as a trusted extension of the CEO’s voice by drafting, editing, and coordinating high-stakes internal and external communications.
• Drive clarity and alignment by ensuring CEO-level messages land clearly, consistently, and at the right altitude.
• Ensure commitments made by the CEO are documented, tracked, and followed through across the organization.
• Maintain a reliable system to track open decisions, action items, and commitments, ensuring nothing drops.
• Proactively chase resolution across teams without requiring CEO intervention.
• Partner closely with Finance, People, and Leadership to ensure smooth execution of CEO-led initiatives.
• Plan and execute complex logistics for leadership offsites, board meetings, and founder-hosted events with minimal friction and zero surprises.
• Prepare agendas, materials, and run-of-show plans; provide in-room or on-site support where required.
• Manage travel end-to-end with a bias toward efficiency, comfort, and contingency planning.
• Leverage AI and automation to increase efficiency for both the role and the CEO; actively experiment and share learnings, spreading fluency and success to all layers of the business.
• Build and continuously improve systems that reduce manual work, decision fatigue, and coordination overhead.
• Identify recurring inefficiencies and independently implement better ways of working.
• Represent the CEO’s office with professionalism, warmth, and discretion.
• Act as a trusted, approachable entry point for all levels of the organization.
• Contribute meaningfully to culture-building efforts, events, and founder-led initiatives.
  
  

What You Bring

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

• 5+ years supporting senior executives (CEO or founder strongly preferred) in fast-moving, high-context environments.
• Proven experience managing complex executive calendars where prioritization and judgment materially impact outcomes.
• Demonstrated ability to operate autonomously, make decisions, and resolve issues without constant direction.
• Strong executive-level writing skills; able to draft clear, concise, and context-aware communications.
• Track record of discretion, integrity, and sound judgment with sensitive information.
• Deep fluency in modern productivity tools (Google Workspace, Slack, Zoom, expense tools) and comfort adopting new systems quickly.
• Practical experience using AI tools (LLM, agents, and more) to increase efficiency, reduce manual work, or improve output quality.
• Experience supporting board meetings, leadership offsites, or high-stakes executive events.
• Exceptionally organized, calm under pressure, and unfazed by ambiguity.
• Direct, pragmatic, and comfortable pushing back when needed — in service of better outcomes.
• Curious, resourceful, and biased toward improvement rather than maintenance.
• Approachable and grounded, with the emotional intelligence to work across all levels of the organization.
• Brings professionalism, perspective, and appropriate humor to demanding environments.
• Based in Toronto, with flexibility to attend in-person meetings and events as required.
  
  

Compensation & Perks

We believe in fair, transparent compensation. Starting salary for this role is $90,000 to $110,000, depending on previous experience and skillset, plus a 10% annual bonus 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 based in Toronto who are willing and able to attend in-person meetings and events on an ad hoc basis.

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.