Head of Operations

Location:
Hybrid

Employment type:
Full-Time

Total Comp:
$100k – $120k CAD + performance bonus

About Sidekick

Sidekick's mission is to help people recover faster from persistent injuries. Trusted by Olympic athletes and everyday customers alike, our products are used by hundreds of thousands of people worldwide and have been featured in Men's Health, Running Magazine, and more.

We are entering a period of rapid growth (2.5× this year, ~3× the following year) with expanding product lines and international markets. Operations is now a critical driver of our ability to scale sustainably.

About the Role

We are hiring a
hands-on
Head of Operations to lead, execute, and scale Sidekick's global operations.

This role is for an experienced operator (10+ years) who can plan ahead, execute directly, and build systems that scale. You will own inventory planning, supply chain, fulfillment, and operational decision-making while leading a small team.

This is a
player–leader role
. You will personally build models, make decisions, and step in where needed—while also designing the systems and coaching the team that will support continued growth.

What You'll Own

1. Inventory, Forecasting & Supply Planning

• Personally build and own detailed Excel-based forecasting and inventory models
• Design reorder points, safety stock, lead-time, MOQ, and in-stock availability targets
• Forecast demand based on growth plans, marketing activity, launches, and promotions
• Translate Excel models into clear requirements for internal tools and apps
• Prevent stockouts without overbuying inventory
• Balance availability, lead times, and cash efficiency

2. Cash Efficiency & Inventory Discipline

• Treat inventory as tied-up cash, balancing growth needs without trapping excess capital
• Improve unit economics and contribution margin through better buying, freight, warehousing, and inventory aging decisions
• Make inventory tradeoffs explicit so leadership understands the cash and margin impact of decisions

3. Global Fulfillment & Warehouse Scaling

• Lead a multi-warehouse operation (Canada & USA initially; UK and Asia next)
• Own 3PL relationships, performance, and expansion into new regions
• Ensure inventory accuracy, clean data, and operational visibility across systems

4. Planning & Decision Rhythm

• Set up a simple planning rhythm so demand, inventory, and cash decisions happen early
• Run weekly/monthly reviews focused on risk, constraints, and upcoming decisions
• Build simple dashboards and leading indicators (weeks of cover, inbound risk, inventory health)
• Introduce tools, automation, or SOPs where they materially reduce risk or manual effort

5. Leadership, Coaching & Decision Quality

• Lead and develop a small operations team (currently 4 people)
• Coach and mentor team members to improve how they think and plan
• Challenge assumptions and surface risks early, with clear recommendations
• Act as a strategic thought partner to the CEO and cross-functional leaders

Who You Are

• Senior operations leader with 10+ years experience
  in ecommerce, DTC, or consumer products
• Deeply hands-on with inventory planning
  – you personally build complex Excel models
• Advanced Excel / spreadsheet skills
  – comfortable modeling demand, scenarios, and tradeoffs
• Experienced people manager
  who coaches and elevates teams
• Forward-looking and anticipatory
  – you consistently see issues coming and act early to prevent them
• Independent and intellectually honest
  – you push back when data suggests a better approach
• Comfortable in small, fast-growing teams
  where you lead by doing
• Experience with multi-warehouse or global operations
  is strongly preferred

What Success Looks Like

• Stockouts are rare, predictable, and planned—not surprises
• Inventory supports growth without trapping excessive cash
• New warehouses and regions launch smoothly
• Leadership can see problems coming early and has time to act
• Operations scales faster than headcount

Why This Role Matters

Sidekick is at an exciting inflection point. As we grow across products, regions, and channels, operations must evolve from reacting to growth into actively enabling it.

This role exists to bring foresight, structure, and discipline to how we plan inventory, capacity, and expansion—so decisions happen earlier, risks are visible sooner, and growth feels controlled rather than chaotic.

Final Note

We value operators who think critically, challenge assumptions, and take ownership of outcomes—not just execution.

We are not looking to solve operational challenges by simply carrying more inventory. We are looking for someone who can support rapid growth with discipline, foresight, and strong judgment.

Benefits

• Competitive compensation + Performance-based bonus
• Comprehensive health benefits
• High ownership and decision-making autonomy
• Direct partnership with the CEO on strategic decisions
• Opportunity to build and scale the operations function
• Dedicated, collaborative, and supportive colleagues
• Fast-paced, high-impact environment during a period of rapid growth
• Hybrid role with work-from-home flexibility

To apply

Please fill in the form to apply:

All applicants who have not filled in the form will not be considered.