Customer Success - Retention & Expansion (Remote)

Job Description

Who We Are

At BrightOrder, we power the fleets that keep the world moving.

Our EMDECS platform and connected hardware solutions help operators run smarter, safer, and more profitably. As we scale, retention and customer growth are mission-critical.

This role is not about maintaining accounts.

It’s about protecting revenue, strengthening relationships, and turning risk into opportunity.

The Role

We’re looking for a high-energy, commercially minded Customer Success & Retention Specialist who thrives in conversations that matter.

You will own renewals, handle cancellation calls, proactively reach out to at-risk customers, and ensure we deliver measurable value.

If you’re someone who stays calm under pressure, doesn’t avoid difficult conversations, and sees churn as a challenge to solve, this role is for you.

What You’ll Do

Own Retention & Renewals

• Manage renewals from 90 days pre-expiry to signature
  
  
• Lead renewal conversations with confidence and clarity
  
  
• Execute save strategies for at-risk accounts
  
  
• Reduce churn through proactive engagement
  
  

Drive Proactive Outreach

• Conduct regular outbound health-check and renewal calls
  
  
• Handle inbound support and cancellation calls professionally
  
  
• Identify upsell and expansion opportunities
  
  

Be the Customer Advocate

• Build trusted relationships across customer accounts
  
  
• Take ownership of issues end-to-end no open loops
  
  
• Collaborate with Product, QA, and Development teams via HubSpot and Jira
  
  

Track & Act on Data

• Monitor customer health scores and KPIs
  
  
• Identify churn signals early
  
  
• Use AI tools (ChatGPT, HubSpot AI, Copilot, Fin.AI) to improve communication, reporting, and efficiency

Requirements

How You’ll Win Here

Retention Impact – You consistently hit renewal and retention targets

Outreach Discipline – You maintain high proactive call velocity

Save Performance – You recover cancellation requests and rebuild trust

Customer Confidence – Customers feel heard and supported

Operational Excellence – Your processes are clean and measurable

What You Bring

• 3–5 years in Customer Success, Account Management, or SaaS retention roles
  
  
• Proven experience handling renewal and cancellation conversations
  
  
• Strong commercial instinct and comfort discussing contracts and value
  
  
• High emotional intelligence and resilience under pressure
  
  
• Excellent time management and ability to prioritize in a fast-paced environment
  
  
• Fluency in English (French and/or Spanish an asset)
  
  
• Experience with HubSpot, Jira, or similar CRM tools
  
  
• Hands-on use of AI tools for productivity and communication
  
  
• Self-starter attitude in a fully remote environment
  
  

Culture & Expectations

We value ownership, accountability, and clarity.

We don’t avoid hard conversations.

We solve them.

We move fast, stay organized, and support each other.

If you’re reading this and thinking, “I want responsibility and impact,” keep going.

Benefits

Why BrightOrder

100% Remote – Work from anywhere in Canada 

Competitive salary: $65,000–$85,000 CAD 

Compensation tied to renewal KPIs

Growth culture – Mentorship and internal mobility

Access to cutting-edge AI tools

Comprehensive company paid health and dental benefits

Paid vacation & personal days

If this sounds like you, don’t just apply and show us why.

Tell us why you thrive in high-accountability environments and how you approach renewals, retention, and tough conversations.

At BrightOrder, we don’t hire passengers.

We hire builders who protect revenue and raise the bar.