About the RoleWe're an early-stage startup looking for a Customer Success Associate to help us scale while maintaining a high bar for customer experience.This role has one job: making sure our customers are supported, successful, and never left guessing. You'll own front-line support, work closely with product and CX leadership, and grow into broader ownership of the customer journey as you build product and industry knowledge.This is a great role for someone who enjoys being close to customers and product, is comfortable in a startup environment, and takes initiative once they understand the context.You won't be handed a rigid playbook. Training is hands-on and shadow-based, and once you're up to speed, you'll be trusted and empowered to identify problems and proactively work toward solutions.What You'll Be Responsible ForFront-Line Support & CX OperationsOwn incoming customer support requests through tickets in HubSpotRespond promptly and professionally to customer inquiriesTroubleshoot issues and resolve them independently when possibleEscalate product or technical issues with clear context when neededTrack trends in customer questions and feedback, and share insights with the teamDocument what you learn so the next person (or customer) finds the answer fasterEnsure customers feel supported, informed, and followed up withThis role is not a call-center-style support position. Success is driven by quality, ownership,



and judgment — not ticket volume.Building Customer KnowledgeDevelop real working knowledge of the product and how customers actually use itUnderstand our customers' operations well enough to anticipate what they needRecognize when a customer's needs point to something more we can do for them, and flag expansion or upsell opportunities to the teamPartner with product to make sure customer pain gets translated into real fixesWhere This Role Is HeadedWe're hiring for the person, not just the opening. As you build context and trust, ownership expands. Over time, this role grows to include:Phone support — being a live voice for customers, not just an inboxOwning the onboarding flow — guiding new customers from signed to fully up and running, and improving that process as you learn where it breaksProactive account outreach — checking in before problems surface rather than waiting for a ticketShaping how we deliver customer success as the company scalesNone of this is expected on day one. It's the direction we're building toward, and we're looking for someone who wants to grow into it.What We're Looking ForComfortable working in a startup or fast-moving environmentA self-starter who takes initiative after gaining contextStrong written and verbal communication skillsOrganized, detail-oriented,



and reliable with follow-throughComfortable interacting with customers directly, including over the phoneWilling to learn new tools, workflows, and skillsAble to make judgment calls and elevate thoughtfully when neededWe work with customers whose businesses run on equipment, schedules, and job sites. You don't need to know that world coming in, but an interest in learning how it actually works will make this role a lot more rewarding.Nice to HavesPrior experience in customer support, customer success, or operationsExperience supporting a SaaS product or troubleshooting software workflowsExperience with customer onboarding or implementationFamiliarity with HubSpot or a similar CRM / ticketing systemExperience working at an early-stage startup or small teamExperience with JIRA or other project management toolsExposure to construction, equipment, or another field-operations industryThese are a bonus, not requirements. We're happy to train the right person who brings strong fundamentals and curiosity.Training & SupportBecause we're a startup, training is practical and hands-on, not rigid or overly formal.You'll begin with a shadowing and ramp-up periodOwnership will increase as you gain familiarity with the product and customersYou'll have transparent escalation paths and access to leadership supportOnce trained, you'll be empowered to solve problems proactively, not just pass them alongAs you demonstrate readiness, we'll expand your scope toward phone support and onboarding ownership#J-18808-Ljbffr

📌 Automotive Customer Success Associate (Temp) - $65,000 - $80,000 A Year (Winnipeg)
🏢 Caribou
📍 Winnipeg