About the Role We'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 setting, 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 For Front-Line Support & CX Operations

Own incoming customer support requests through tickets in HubSpot

Respond promptly and professionally to customer inquiries

Troubleshoot issues and resolve them independently when possible

Escalate product or technical issues with clear context when needed

Track trends in customer questions and feedback, and share insights with the team

Document what you learn so the next person (or customer) finds the answer faster

Ensure customers feel supported, informed, and followed up with

This role is not a call-center-style support position. Success is driven by quality, ownership, and judgment — not ticket volume.

Building Customer Knowledge

Develop real working knowledge of the product and how customers actually use it





Understand our customers' operations well enough to anticipate what they need

Recognize when a customer's needs point to something more we can do for them, and flag expansion or upsell opportunities to the team

Partner with product to make sure customer pain gets translated into real fixes

Where This Role Is Headed We'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 inbox

Owning the onboarding flow — guiding new customers from signed to fully up and running, and improving that process as you learn where it breaks

Proactive account outreach — checking in before problems surface rather than waiting for a ticket

Shaping how we deliver customer success as the company scales

None 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 For

Comfortable working in a startup or fast-moving environment

A self-starter who takes initiative after gaining context

Strong written and verbal communication skills

Organized, detail-oriented, and reliable with follow-through





Comfortable interacting with customers directly, including over the phone

Willing to learn new tools, workflows, and skills

Able to make judgment calls and elevate thoughtfully when needed

We 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 Haves

Prior experience in customer support, customer success, or operations

Experience supporting a SaaS product or troubleshooting software workflows

Experience with customer onboarding or implementation

Familiarity with HubSpot or a similar CRM / ticketing system

Experience working at an early-stage startup or small team

Experience with JIRA or other project management tools

Exposure to construction, equipment, or another field-operations industry

These are a bonus, not requirements. We're happy to train the right person who brings strong fundamentals and curiosity.

Training & Support Because we're a startup, training is practical and hands-on, not rigid or overly formal.

You'll begin with a shadowing and ramp-up period

Ownership will increase as you gain familiarity with the product and customers

You'll have clear escalation paths and access to leadership support

Once trained, you'll be empowered to solve problems proactively, not just pass them along

As you demonstrate readiness, we'll expand your scope toward phone support and onboarding ownership

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📌 Customer Experience Associate (Winnipeg)
🏢 Tough Commerce
📍 Winnipeg