Join to apply for theHead of Operations (Ecommerce)role atSidekickThis range is provided by Sidekick. Your actual pay will be based on your skills and experience — talk with your recruiter to learn more.Base pay rangeCA$100,000.00/yr - CA$120,000.00/yrDirect message the job poster from SidekickTotal Comp:$100k – $120k CAD + performance bonusAbout SidekickSidekick’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 RoleWe are hiring ahands‑onHead 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 aplayer‑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 Own1. Inventory, Forecasting & Supply PlanningPersonally build and own detailed Excel‑based forecasting and inventory modelsDesign reorder points, safety stock, lead‑time, MOQ, and in‑stock availability targetsForecast demand based on growth plans, marketing activity, launches, and promotionsTranslate Excel models into clear requirements for internal tools and appsPrevent stockouts without overbuying inventoryBalance availability, lead times, and cash efficiencyTreat inventory as tied‑up cash,



balancing growth needs without trapping excess capitalImprove unit economics and contribution margin through better buying, freight, warehousing, and inventory aging decisionsMake inventory trade‑offs explicit so leadership understands the cash and margin impact of decisions3. Global Fulfillment & Warehouse ScalingLead a multi‑warehouse operation (Canada & USA initially; UK and Asia next)Own 3PL relationships, performance, and expansion into new regionsEnsure inventory accuracy, clean data, and operational visibility across systems4. Planning & Decision RhythmSet up a simple planning rhythm so demand, inventory, and cash decisions happen earlyRun weekly/monthly reviews focused on risk, constraints, and upcoming decisionsBuild simple dashboards and leading indicators (weeks of cover, inbound risk, inventory health)Introduce tools, automation, or SOPs where they materially reduce risk or manual effort5. Leadership, Coaching & Decision QualityLead and develop a small operations team (currently 4 people)Coach and mentor team members to improve how they think and planChallenge assumptions and surface risks early, with clear recommendationsAct as a strategic thought partner to the CEO and cross‑functional leadersWho You AreSenior operations leader with 10+ years experiencein ecommerce, DTC, or consumer productsDeeply hands‑on with inventory planning– you personally build complex Excel modelsAdvanced Excel / spreadsheet skills– comfortable modeling demand, scenarios,



and trade‑offsExperienced people managerwho coaches and elevates teamsForward‑looking and anticipatory– you consistently see issues coming and act early to prevent themIndependent and intellectually honest– you push back when data suggests a better approachComfortable in small, fast‑growing teams where you lead by doingExperience with multi‑warehouse or global operations is strongly preferredWhat Success Looks LikeStockouts are rare, predictable, and planned—not surprisesInventory supports growth without trapping excessive cashNew warehouses and regions launch smoothlyLeadership can see problems coming early and has time to actOperations scales faster than headcountWhy This Role MattersSidekick 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 NoteWe 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.Competitive compensation + Performance‑based bonusHigh ownership and decision‑making autonomyDirect partnership with the CEO on strategic decisionsOpportunity to build and scale the operations functionDedicated, collaborative, and supportive colleaguesFast‑paced, high‑impact workplace during a period of rapid growthHybrid role with work‑from‑home flexibilityTo applyPlease fill in the form to apply: https://sidekicktool.Typeform.Com/to/VpcyeAAUAll applicants who have not filled in the form will not be considered.#J-18808-Ljbffr

📌 Head Of Operations (Ecommerce) - C$100,000 - C$120,000 A Year (Toronto)
🏢 Sidekick
📍 Toronto