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Escalation Specialist

Job in Winnipeg, Manitoba, Canada
Listing for: Smarter Contact
Full Time position
Listed on 2026-09-05
Job specializations:
  • Customer Service/HelpDesk
    Customer Success Management
Job Description & How to Apply Below
Smarter Contact is the market-leading AI-powered text and voice communications platform for real estate professionals in the US market.

We’re building a best-in-class product with world-class talent to serve customers who rave about us. Will you join us?

About you:

This is a direct-hire role. As a Customer Escalation Specialist, your primary responsibility is to reduce churn and protect revenue. You will proactively engage canceled and churned accounts via calls, text, and emails to understand why. Most importantly, you’ll be the bridge that enables customer success, helping us retain them. As a result, retained revenue will follow with subscription renewals, of which you will be responsible for attaining a monthly quota.

What You’ll Own:

Responsible for reducing churn by retaining customers and revenue.

You’ll own a monthly customer retention quota as your main KPI.

Apply approved retention strategies (in-app credits, billing credits, plan downgrades, and success enablement) within defined guidelines.

Intercept downgrade requests and reposition value through usage planning, campaign scheduling, and ROI alignment before the plan change is approved.

Identify and recover failed onboarding cases by re-driving activation and time-to-first-value.

Perform proactive outreach to low-usage and disengaged accounts using structured “silent churn” playbooks to re-engage customers before cancellation intent surfaces.

Working with the Success team, diagnose root causes of underperformance (targeting, messaging, timing, setup) and implement corrective actions that directly improve campaign outcomes.

What We’re Looking For:

5+ years in a customer retention, client recovery, escalations or related role.

Conduct 50+ weekly retention calls via phone or Google Meet.

Proven ability to analyze customer behavior, identify churn risks, and take targeted action to retain accounts.

Strong objection handling, negotiation, and behavioral communication skills with the ability to influence customer decisions under pressure.

Ability to diagnose and act on different churn drivers (budget, usage, performance, lifecycle, compliance) with tailored retention strategies.

Able to work efficiently in a high-activity environment without sacrificing quality.

Comfortable holding long-format video calls for reviewing customer accounts and demonstrating product value.

Coachable, performance-driven, accountable, and a strong team player.

Proficient or native level English (full business fluency).

Work a minimum of 40 hours/week between 10 am and 7 pm EST, Monday to Friday.

Experience working at a CPaaS or Martech SaaS company.

Experience working with real estate professionals.

USD base compensation

15 days PTO + 5 sick days + 10 floating holidays (6 weeks off)

High autonomy, fast execution, real impact

Professional development and wellness incentives

Employment anniversary and birthday gift

Remote-first team with a strong performance culture

This opportunity is offered as a full-time independent contractor role

Please Don’t Apply If:

You’re not fluent in English or are uncomfortable communicating directly with cross-functional teams

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