Customer Retention Supervisor (contract)

Coinflip-; Chicago (IL); Remote; USD 65,000 - 95,000; Part time

Job summary

CoinFlip is seeking a results-driven Customer Retention Supervisor to lead the retention team in a fully remote contract role.

The role combines coaching, outbound engagement, SOP development, and data-driven improvement to drive repeat transactions and revenue.

Ideal candidates will have 3+ years supervisory experience, experience with CRM tools, and a proactive, sales-oriented approach.

Qualifications

• Bachelor's degree preferred but not required.
• 3+ years supervisory/leadership in retention/outbound sales.
• Experience managing performance-driven teams in outbound outreach.
• Proven success in conversion, retention, reactivation, relationships.
• Experience developing SOPs, workflows, call scripts, and training materials.
• Strong coaching, leadership, and communication.
• Drive agent productivity and KPIs.
• Analytical skills with data-driven strategies.
• Balance hands-on engagement with team management.
• Organizational skills, detail-oriented, independent.
• Proficient in Excel and CRM/outbound platforms.

Responsibilities

• Lead, coach, and manage Customer Retention Specialists with clear performance expectations.
• Conduct outbound calls to engage customers and support retention campaigns.
• Develop and maintain SOPs, workflows, scripts, and training materials.
• Manage daily outreach activities, schedules, and campaign assignments.
• Drive first-to-second transaction conversion and reactivation.
• Execute retention campaigns with offers and incentives.
• Monitor KPIs: calls, contacts, conversion, retention, revenue.
• Conduct regular reviews and coaching to improve engagement.
• Analyze activity and campaigns to identify retention opportunities.
• Maintain CRM records, scorecards, and performance reporting.
• Handle escalations and support complex interactions.
• Collaborate with Marketing, Support, Sales, Ops, Compliance.
• Ensure all activities comply with policies and regs.
• Assist hiring, onboarding, and training of retention team.
• Other duties as assigned.

Skills

Leadership

Coaching

Outbound calls

KPI tracking

CRM analytics

SOP development

Performance mgmt

Education

Bachelor's degree preferred

Tools

Salesforce

Zendesk

Five9

Amazon Connect

Job description

All Jobs > Customer Retention Supervisor (contract)

Customer Retention Supervisor (contract)
Fully Remote Remote

Contract

Description

CoinFlip is a global digital currency platform company, focused on providing consumers with simple and secure access to buy and sell cryptocurrency. The company operates the world's largest network of cryptocurrency kiosks by transaction volume with more than 5,500 kiosks the United States, Canada, Australia, New Zealand, South Africa and Italy. CoinFlip’s digital currency kiosks make buying and selling major cryptocurrencies accessible and safe for consumers who wish to purchase their digital currency using cash. CoinFlip also operates CoinFlip Preferred, a personalized over-the-counter service that provides investors with custom, white glove support for their cryptocurrency transactions. In 2022, CoinFlip launched CoinFlip Ventures, an investment group offering coaching, funding, and networking support to early-stage crypto and web3 projects. CoinFlip recently received authorization under the European Union’s Markets in Crypto-Assets Regulation (MiCA), marking an important milestone in the company’s continued expansion of regulated digital asset services across Europe.

Headquartered in Chicago, CoinFlip placed in the top 500 on the 2021, 2022, and 2023 Inc. 5000 list, and on the 2022 and 2023 Deloitte Technology Fast 500, was named the 2021 and 2022 #1 fastest-growing company in Chicago by Crain's, ranked in Chicago Tribune’s Top Workplaces in 2021 and 2022, and was awarded the 2021 and 2022 Stevie ® Awards for Customer Service. To learn more about CoinFlip and how to get started on your digital currency journey, visit www.coinflip.tech .

We are seeking a results-driven Customer Retention Supervisor to lead our customer retention team and drive repeat transactions, customer reactivation, and revenue growth. This is a hands-on leadership role combining team management, direct outbound customer engagement, campaign execution, and process development.

The ideal candidate is a proactive, sales-oriented leader who can coach agents, personally engage customers, develop standard operating procedures (SOPs), and leverage performance data to improve customer retention, team productivity, and overall results.

Responsibilities

• Lead, coach, and manage Customer Retention Specialists, establishing clear performance expectations and accountability for results.
• Personally conduct outbound calls to engage customers, encourage repeat transactions, reactivate inactive customers, and support retention campaigns.
• Develop, implement, and maintain SOPs, outbound calling workflows, customer engagement processes, scripts, and training materials.
• Manage daily outreach activities, agent schedules, campaign assignments, and follow-up priorities to maximize productivity.
• Drive first-to-second transaction conversion, high-value customer retention, and customer reactivation through targeted outreach initiatives.
• Develop and execute retention campaigns, including promotional offers, discount incentives, abandoned transaction follow-ups, and customer reactivation programs.
• Monitor individual and team KPIs, including outbound calls, customers contacted, conversion rates, repeat transactions, reactivation rates, transaction volume, and revenue.
• Conduct regular call reviews, performance evaluations, and coaching sessions to improve agent effectiveness and customer engagement.
• Analyze customer activity, transaction patterns, and campaign results to identify retention opportunities and improve outreach strategies.
• Maintain accurate CRM records, agent scorecards, and daily, weekly, and monthly performance reporting.
• Handle escalated customer concerns, resolve objections, and support complex customer interactions.
• Collaborate with Marketing, Customer Support, Sales, Operations, and Compliance to execute retention initiatives and improve the customer experience.
• Ensure all outreach activities, customer communications, and retention processes comply with company policies and applicable regulations.
• Support hiring, onboarding, and training of retention team members.
• Other duties as assigned.

Qualifications

• Bachelor's degree preferred but not required.
• Minimum of 3 years of supervisory or leadership experience in customer retention, outbound sales, contact center operations, or related field.
• Proven experience managing performance-driven teams while actively participating in outbound customer outreach.
• Demonstrated success in customer conversion, retention, reactivation, and relationship management.
• Experience developing SOPs, operational workflows, call scripts, and training materials.
• Strong coaching, leadership, objection-handling, and customer communication skills.
• Ability to manage agent productivity, establish KPIs, and drive measurable performance improvements.
• Strong analytical skills with experience interpreting performance data and developing actionable strategies.
• Ability to balance hands-on customer engagement with team management and operational responsibilities.
• Strong organizational skills, attention to detail, and ability to work independently in a fast-paced environment.
• Proficiency in Microsoft Office Suite, particularly Excel, and experience with CRM and outbound calling platforms.

Preferred Qualifications

• Experience in fintech, financial services, cryptocurrency, or other transaction-based businesses.
• Experience managing outbound retention campaigns, customer reactivation programs, and promotional incentives.
• Experience building or scaling customer retention processes and performance reporting.
• Knowledge of cryptocurrency and blockchain technology.
• Experience working in a regulated environment.
• Familiarity with Salesforce, Zendesk, Five9, Amazon Connect, or similar platforms.

Compensation

Working at CoinFlip means collaborating with experienced and innovative leaders who share a clear vision and a track record of success. We offer a collaborative and positive working environment where we encourage employees to balance productivity with time to recharge. Compensation is above and beyond a typical “startup” — we offer competitive salaries, performance-based incentives, and competitive benefits for full-time employees.

CoinFlip values diversity in the workplace and is an equal opportunity employer committed to providing an inclusive and accessible work environment. We thank all candidates who apply, but only those selected for an interview will be contacted.

By applying to this role, you give express consent to CoinFlip to send you informational text (SMS) messages regarding this role and the application process. You can cancel the SMS service at any time by replying "STOP" to the text message you received. If at any time you forget what keywords are supported, just reply "HELP." Message and data rates apply. If you require a special accommodation, please let us know and we’ll work with you to meet your needs.