• Skip to primary navigation
  • Skip to main content
  • Skip to footer

Side Hustles

Side Hustles

Side Hustles For All

  • Best Side Hustles
    • Woman sitting on a pile of coins and working on a laptop surrounded by icons representing different side hustle ideas

      31 Best Side Hustles to Earn Extra Money in 2026

    • Bicycle courier delivering food for their side hustle.

      What Is a Side Hustle?

    • Remote worker sitting at his desk making money from home

      18 Ways to Make Money from Home (Online and Offline Jobs)

    • By Category
      • Arts & Crafts
      • Business Services
      • Caregiving
      • Creative Services
      • Digital Freelance Services
      • View All
    • By Lifestyle
      • I’m introverted
      • I’m a man
      • I’m a woman
      • I’m a stay-at-home mom
      • I’m unique
      • View All
    • By Profession
      • Artists & Creatives
      • Musicians
      • Nurses
      • Physicians
      • Teachers
      • View All
    • By Age Group
      • College Students
      • Teens
      • Age 50+
      • Seniors
      • View All
    • By Skills & Interests
      • Get Paid to Lose Weight
      • Get Paid to Play Games
      • Get Paid to Read
      • Get Paid to Sleep
      • Get Paid to Travel
      • View All
  • Best Gig Apps
    • Freelance worker popping out of a phone screen and considering gig apps on the App Store and Google Play

      Top 6 Gig Apps to Make Real Cash in 2026

    • Smartphone surrounded by the icons of different money-making apps

      Top 10 Best Money-Making Apps to Try in 2026

    • two teenagers using job apps on a phone and laptop

      19 Job Apps for Teens to Find Jobs and Make Money

    • By Gig Type
      • Cashback
      • Data Entry
      • Delivery
      • Games
      • Product Testing
      • View All
    • By Payment Method
      • Bingo Games that Pay to Cash App
      • Games that Pay Real Money
      • Games that Pay to Cash App
      • Games that Pay via PayPal
      • Surveys that Pay to Cash App
      • View All
    • By Benefits
      • $20 Signup Bonuses
      • $25 Signup Bonuses
      • $50 Signup Bonuses
      • Best Signup Bonuses
      • Instant Signup Bonuses
      • View All
    • By Skills & Interests
      • Driving
      • Losing Weight
      • Playing Games
      • Product Testing
      • Watching Ads
      • View All
  • Job Hunting
    • Freelance worker browsing a job post on a freelance job board.

      23 Job Boards You Can Use to Find Remote Work

    • Freelance writer sitting at her laptop working on a project

      15 Best Remote Jobs That Require No Paid Work Experience

    • Teenager sitting at laptop working an online job

      14 Online Jobs for Teens (With No Experience)

    • Freelancing
      • Freelance Writing Sites
      • Freelance Writing Job Boards
      • Freelance Writing Platforms
      • View More
    • Gig & Shift Work
      • Gig Work Apps
      • On-Demand Work Apps
      • Shift Work Apps
      • View More
    • GPT (Get Paid To)
      • Microtasking
      • Product Testing
      • Survey Taking
      • View More
    • Remote Working
      • Best Remote Job Boards
      • Top 15 Remote Jobs
      • View More
  • Job Board
    • Work Schedule
      • Part-Time Jobs
      • Per-Diem Jobs
      • Go Search
    • Work Environment
      • Hybrid Jobs
      • Remote Jobs
      • Go Search
    • Employment Type
      • Contractor Jobs
      • Internship Jobs
      • Temporary Jobs
      • Go Search
    • Job Title
      • Accounting Jobs
      • Data Entry Jobs
      • Nursing Jobs
      • Online Teaching Jobs
      • Software Engineer Jobs
      • Go Search
    • State
      • California Jobs
      • Florida Jobs
      • New York Jobs
      • Pennsylvania Jobs
      • Texas Jobs
      • Go Search
    • City
      • Chicago, IL
      • Houston, TX
      • Los Angeles, CA
      • New York City, NY
      • Phoenix, AZ
      • Go Search

Home Flexible Job Board Client Relationship & Retention Specialist

$6,000–8,000/mo 23d ago

Client Relationship & Retention Specialist

Boost your chances before you apply.

  • ✨ Apply 10x Faster Free

    It takes 30+ tailored applications to land jobs like this one. We'll help you get that done in 1 hour.

    No Credit Card Required

  • Proceed to Application Go directly to the company's job page to apply.
Logo

AI Acquisition

Orlando, FL, US

Full-time Permanent Remote

✨ Apply 10x Faster

Analyze your resume for missing keywords, then one-click optimize it. Don't be anything less than a 100% match candidate.

Free

No Credit Card Required

Summary

The specialist will manage at-risk customer relationships by diagnosing root causes of dissatisfaction and implementing recovery plans. They will coordinate across internal teams to resolve complex issues while maintaining high standards of customer trust and retention.

Job Description

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
  • 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
  • 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

About the company

AI Acquisition

We connect businesses and empower entrepreneurs with AI that helps them achieve more, automate the boring parts of business and allow them to focus on work that can change lives. $308,960 is the average cash collected by our clients.

Welcome to AI Arbitrage.

We’ve partnered with 1200+ businesses to improve their lives and business with AI:

In a survey of over 660 businesses with over 100 responding, business owners averaged $18,105 in monthly revenue after implementing our system.

1. Business Set-up Ai Agents
Launch your AI business. Creating your website, logo and social media accounts. Choosing your niche and selecting AI systems.

2. Selling Ai Agents
Ai Agents to write cold emails, AI Agents to create a sales proposal, AI Agents to Analyse your Sales Calls

3. Deliver
License our advanced AI systems and install them into your client's business to deliver exceptional results

4. Scale
Leverage a team of AI Agents to potentially take on more clients compared to if you were just doing this yourself

Then potentially place a proven operator and train them to manage the AI agents so you get out of the day-to-day.

It’s how we’ve been able to get results like these…

➤ KinCreative went from $50,000 to $250,000/mo in 12 months
➤ DLI scaled from $100,000 to $200,000/mo
➤ Olive Group - $2 - $10M/year
➤ Social Profit Media hit $3.6M/yr
➤ Impact Orthodontics hit $5M/yr
➤ Rik went from a corporate job to $32,000/mo
➤ Joe went from a corporate sales job to $40,000/mo while doing this part-time
➤ Elizabeth went from working a depressing 9-5 as an admin assistant to making $75,000

DISCLAIMER: All testimonials shown are real, but do not claim to represent typical results. Any success depends on many variables, which are unique to each individual, including commitment and effort. Testimonial results are meant to demonstrate what the most dedicated students have do

Company size

51-200 employees

Industry

Business Consulting and Services

Org type

Privately Held

Apply Now

About the company

AI Acquisition

We connect businesses and empower entrepreneurs with AI that helps them achieve more, automate the boring parts of business and allow them to focus on work that can change lives. $308,960 is the average cash collected by our clients.

Welcome to AI Arbitrage.

We’ve partnered with 1200+ businesses to improve their lives and business with AI:

In a survey of over 660 businesses with over 100 responding, business owners averaged $18,105 in monthly revenue after implementing our system.

1. Business Set-up Ai Agents
Launch your AI business. Creating your website, logo and social media accounts. Choosing your niche and selecting AI systems.

2. Selling Ai Agents
Ai Agents to write cold emails, AI Agents to create a sales proposal, AI Agents to Analyse your Sales Calls

3. Deliver
License our advanced AI systems and install them into your client's business to deliver exceptional results

4. Scale
Leverage a team of AI Agents to potentially take on more clients compared to if you were just doing this yourself

Then potentially place a proven operator and train them to manage the AI agents so you get out of the day-to-day.

It’s how we’ve been able to get results like these…

➤ KinCreative went from $50,000 to $250,000/mo in 12 months
➤ DLI scaled from $100,000 to $200,000/mo
➤ Olive Group - $2 - $10M/year
➤ Social Profit Media hit $3.6M/yr
➤ Impact Orthodontics hit $5M/yr
➤ Rik went from a corporate job to $32,000/mo
➤ Joe went from a corporate sales job to $40,000/mo while doing this part-time
➤ Elizabeth went from working a depressing 9-5 as an admin assistant to making $75,000

DISCLAIMER: All testimonials shown are real, but do not claim to represent typical results. Any success depends on many variables, which are unique to each individual, including commitment and effort. Testimonial results are meant to demonstrate what the most dedicated students have do

Company size

51-200 employees

Industry

Business Consulting and Services

Org type

Privately Held

Footer

sidehustles.com
Facebook Twitter Instagram LinkedIn Reddit TikTok YouTube

Show Me The Money

  • Side Hustle Basics
  • Side Hustle Job Board (Remote & Part-Time Jobs)
  • Gig App Reviews
  • Job Hunting
  • Manage Your Money
  • The Gig Apple: News & Events

Company

  • About Us
  • Contact Us
  • Become a Contributor
  • Advertising & Sponsorships
  • Partner With Us
  • Editorial Guidelines

Side Hustles © All rights reserved

  • Privacy Policy
  • Terms of Service

Thanks for using our free job board

Your review would mean a lot to us.

If you love that we're just giving away remote jobs for free with no paywall, please spread the word. (You will need to create an account on Trustpilot, for which we'll be eternally grateful.) Good luck out there!

Leave a Review Not yet. Send me to the job post.