Remote Customer Success - Retention & Expansion (Remote)

Bilinguallink; Woodstock; Remote; CAD 65,000 - 85,000; Full time

Benefits offered by this job

Remote work nationwide Canada

Competitive CAD salary

Renewal KPI-based compensation

Growth culture

Access to AI tools

Health and dental benefits

Paid vacation & personal days

Job summary

BrightOrder is seeking a Customer Success & Retention Specialist to own renewals, manage at-risk accounts, and drive measurable value for a 100% remote team across Canada.

You'll partner with Product, QA, and Development, leverage HubSpot and Jira, and use AI tools to communicate clearly, report on health metrics, and reduce churn. Join a fast-paced, outcomes-driven culture that values ownership and impact.

Qualifications

• 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.

Responsibilities

• Own renewals from pre-expiry to signature and execute save strategies.
• Lead renewal conversations with confidence and clarity to reduce churn.
• Conduct proactive outbound health-check and renewal calls.
• Collaborate with Product, QA, and Development via HubSpot and Jira.

Skills

Renewal conversations

Commercial instinct

Time management

English fluency

AI-enabled communication

CRM & software literacy

Tools

HubSpot

Jira

CRM tools

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

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.

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

At BrightOrder, we don't hire passengers.

We hire builders who protect revenue and raise the bar.