Client Relationship & Retention Specialist

AI Acquisition Open · verified Sep 11, 2026

Remote Canada Full-time Mid-level Retention Marketing

Mid-level Retention Marketing role at AI Acquisition. Remote, Canada · full-time.

Role brief

Growth Roles summary, based on the employer's posting.

What you'll do

You'll manage customer cases involving disengagement, cancellations, refunds, or declining trust
You'll review each customer's history, then contact them by phone, SMS, or email as appropriate
You'll uncover root causes, resolve suitable issues, and coordinate help from internal teams
You'll guide difficult conversations toward a clear recovery plan and next step
You'll document outcomes and flag recurring retention problems for practical improvement

What you bring

You have experience in consultative sales, retention, customer success, account management, escalations, or similar client work
You can lead emotionally difficult calls, build rapport, and guide customers without pressure or unsupported promises
You investigate thoroughly, identify underlying causes, and distinguish valid concerns from unhelpful conclusions
You bring commercial judgment, strong organization, careful documentation, and ownership across teams
You are resilient, coachable, and willing to review feedback to improve

Who this fits

This role suits someone who can stay composed with frustrated customers while combining empathy, influence, investigation, and sound judgment. You must be comfortable owning complex cases across internal teams and working remotely from Canada. The arrangement is full-time under an Independent Contractor Agreement, with potential growth into broader client operations, customer success, senior, or team-lead work.

From the employer

We are looking for a Client Relationship & Retention Specialist to take ownership of complex customer situations where there is a risk of disengagement, cancellation, refund, or loss of trust.

This is a high-accountability, client-facing role requiring strong judgment, confident phone communication, commercial awareness, and the ability to remain calm and effective in difficult situations.

You will investigate the full customer journey, identify the true cause of an issue, and work directly with customers to help them regain confidence and move forward. This means looking beyond the immediate complaint to understand what is actually driving the customer’s concern, whether that is a practical, technical, delivery, expectation, or mindset blocker.

You will be expected to troubleshoot appropriate issues directly, coordinate across internal teams when additional action is required, and maintain ownership of the customer relationship through resolution.

This is not passive customer support or an aggressive refund-prevention role. It is a high-trust, consultative role for someone who can combine strong call control and influence with genuine curiosity, empathy, and problem-solving.

Success requires the ability to build trust quickly, lead challenging conversations confidently, diagnose problems accurately, and help customers move toward a constructive next step without pressure, manipulation, or unsupported promises.

THE COMPANY

A multi-8-figure ARR business with 200+ team members, bootstrapped and profitable. The company launches and scales information and software products on a marketing and sales engine refined across a dozen product launches and $100M+ in ad spend.

This seat sits within our client operations team and plays an important role in strengthening customer relationships, resolving complex issues, improving retention, and protecting long-term customer value.

WHAT YOU WILL DO

Take ownership of at-risk customer cases involving dissatisfaction, disengagement, cancellation, refund concerns, or loss of confidence
Contact assigned customers quickly by telephone and use SMS and email when appropriate
Review the customer’s complete journey before making contact to understand the history, context, and potential issues
Speak directly with customers by phone and build trust quickly, even when emotions are high
Diagnose practical, technical, delivery, expectation, or mindset blockers and identify the true root cause of the issue
Troubleshoot appropriate issues directly and coordinate additional support when required
Lead calm, confident resolution and de-escalation conversations
Separate the immediate complaint from the underlying issue and determine the most appropriate path forward
Help customers reframe unhelpful conclusions without dismissing legitimate concerns
Reconnect customers with their original goals and help establish a clear recovery plan and next action
Correct misunderstandings clearly and respectfully without becoming defensive or argumentative
Use strong conversational influence and judgment to help restore customer confidence without applying pressure or making unsupported promises
Make sound judgment calls while balancing customer experience, commercial considerations, and the facts of each case
Coordinate with Onboarding, Tech, Delivery, Sales, Finance, and other teams when additional action is required
Maintain ownership of the customer relationship while internal work is being completed rather than simply passing the customer between departments
Use approved support options or concessions when appropriate and justified
Escalate continued refund requests or complex cases through the appropriate process
Keep customers informed while outstanding issues are being resolved
Maintain clear and accurate records of conversations, decisions, commitments, actions, and outcomes
Identify recurring causes of disengagement, dissatisfaction, and refunds and recommend practical improvements to prevent them in the future

Requirements

Previous experience in consultative or high-ticket sales/closing, Customer Retention, Customer Success, Account Management, Escalations, Complaints, Dispute Resolution, Service Recovery, or a similarly high-touch client-facing role
Strong conversational influence and call control, with the ability to confidently lead a customer toward a constructive next step
Strong ability to build rapport with frustrated, disappointed, uncertain, or skeptical customers
Comfortable leading difficult and emotionally charged conversations
Able to listen carefully while remaining confident enough to challenge an unhelpful conclusion when appropriate
Able to recognize legitimate customer or company-side issues rather than treating every concern as a mindset problem
Persuasive without relying on pressure, manipulation, or unsupported promises
Strong investigative and problem-solving skills with the ability to identify root causes rather than simply addressing surface-level issues
Comfortable troubleshooting practical issues and coordinating with other teams when additional expertise is required
Good commercial judgment and an understanding of customer value, retention, and financial impact
Strong organisation, attention to detail, and written documentation skills
Comfortable taking personal ownership of a customer issue and driving it toward resolution across multiple teams
Able to manage multiple complex customer cases and priorities at the same time
High level of integrity and sound judgment when determining the appropriate next step
Reliable, resilient, coachable, and willing to review calls and feedback to continuously improve

Benefits

Full-time opportunity
Independent Contractor Agreement
$6,000–$8,000 USD monthly base, depending on experience
Additional monthly performance incentive based on results
Fully remote
Opportunity to grow into broader Client Operations, Customer Success, senior, or team-lead responsibilities