Kaylin Simmons
Chicago
Summary
Escalation and risk management professional with extensive experience across banking, fintech, and customer support leadership. Skilled in managing high-risk financial cases, leading Tier 2/3 escalation and risk workflows, and resolving complex disputes and unauthorized transaction issues while ensuring compliance, fraud prevention, and customer retention. Known for calm, customer-first de-escalation, strong judgment, and cross-functional partnership in fast-paced, regulated environments.
Overview
10
10
years of professional experience
Work History
Manager, Escalation Specialist/Risk Team Lead
Cash App
01.2024 - Current
- Lead escalation resolution for high-risk banking/financial cases including disputes, unauthorized transactions, account restrictions, and compliance-related issues.
- Manage and support a risk workflow focused on fraud prevention, account monitoring, and financial risk mitigation.
- Serve as point of contact for executive-level and regulatory escalations, resolving complex, time-sensitive complaints while protecting customer experience and financial exposure.
- Handle sensitive financial data and high-value money movement with strict adherence to policies, procedures, and regulatory requirements.
- De-escalate high-conflict interactions through clear communication, empathy, and solution-focused judgment; partner cross-functionally with Compliance, Fraud, and Operations.
- Block, Inc.
Merchant Support Representative (Tier 2)
U.S. Bank
Chicago
01.2022 - 12.2024
- Delivered Tier 2 support for merchant services, resolving terminal issues, billing discrepancies, and payment processing errors.
- Investigated and resolved complex merchant complaints and escalations in alignment with banking regulations and internal policies.
- Supported multiple channels (phone, email, in-app) while maintaining professionalism in high-stress situations.
- Applied advanced troubleshooting and problem-solving to payment disputes and transaction-related technical issues.
- Consistently de-escalated dissatisfied customers while protecting the bank from financial and reputational risk.
Sales/Customer Service Representative
AT&T
Chicago
01.2021 - 12.2022
- Provided high-volume customer support and sales assistance, resolving billing, service, and technical issues in a fast-paced environment.
- Used active listening, de-escalation, and multitasking to manage real-time concerns and maintain customer satisfaction.
- Supported retention through clear education on products/services and timely resolution of issues.
Enrollment Broker
AltaStaff
Chicago
01.2017 - 12.2019
- Delivered inbound/outbound support, educating clients on program options and resolving enrollment issues.
- Managed escalations while adhering to SLAs, quality standards, and compliance requirements.
- Drove full resolution of client concerns to reduce risk and improve overall customer experience.
Administrative Assistant
Next Level Trucking Management
Frankfort
01.2016 - 12.2017
- Managed appointment scheduling, payment processing, and customer inquiries while maintaining accurate client records.
- Handled multiple phone lines and provided prompt, professional resolution to customer concerns.
- Supported daily administrative operations to ensure smooth customer and office workflows.
Education
Diploma -
Lincoln Way East High School
ChicagoSkills
- Escalation & Complaint Management - Expert
- Risk & Fraud Support - Experienced
- Banking & Financial Transactions - Experienced
- De-escalation of High-Conflict Customers - Expert
- Regulatory & Compliance Awareness - Experienced
- Tier 2/3 Support - Experienced
- Salesforce - Skillful
- Microsoft Office (Excel, Word, PowerPoint) - Skillful
- Google Workspace - Skillful
- Multichannel Support (Phone,Email, Chat, In-App) - Experienced
Timeline
Manager, Escalation Specialist/Risk Team Lead
Cash App
01.2024 - Current
Merchant Support Representative (Tier 2)
U.S. Bank
01.2022 - 12.2024
Sales/Customer Service Representative
AT&T
01.2021 - 12.2022
Enrollment Broker
AltaStaff
01.2017 - 12.2019
Administrative Assistant
Next Level Trucking Management
01.2016 - 12.2017
Diploma -
Lincoln Way East High School