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James Jennings

@jamesjennings1

Technical Account Manager with 10+ years in fintech operations, payroll/HR technology, and compliance-driven client success.

United States

Message

What I'm looking for

I’m looking for a fintech/account-ops role where I can own regulated client portfolios, drive SLA and compliance outcomes, and partner with engineering and compliance to eliminate recurring issues and improve customer lifecycle results.

I’m a strategic client relationship leader and fintech operations professional with 10+ years of progressive experience across regulated financial services, payroll, HR technology, and enterprise SaaS environments. I’m relied upon to manage complex account portfolios, resolve escalations, strengthen compliance controls, and optimize service delivery models by driving cross-functional alignment across Engineering, Compliance, Operations, and Client Success.

At Gusto (2025 to 2026), I led technical support for payroll, HR, and benefits platforms, collaborating with Engineering, Compliance, and Operations to resolve platform bugs and workflow disruptions. I headed resolutions of complex payroll and tax filing discrepancies—ensuring 100% accuracy for clients—while implementing workflow improvements that reduced repeat support tickets and accelerated escalation timelines across 3 internal departments to improve client outcomes. Earlier roles (Fifth Third Bank and ADP) reinforced my commitment to regulatory compliance, risk mitigation, audit readiness, and high-quality service delivery in high-volume environments.

Experience

Work history, roles, and key accomplishments

Current

Technical Onboarding Associate

Current

Amplify

Apr 2026 - Present (1 month)

• Serve as the technical liaison between Customer Success, IT administrators, and internal teams to troubleshoot enrollment blockers and ensure smooth transitions from onboarding to long-term adoption
• Manage large-scale roster integrations and data migrations using Clever, ClassLink, and OneRoster (CSV), ensuring 100% data integrity across district SIS and Amplify platforms

Technical Account Manager

Gusto

Jan 2025 - Jan 2026 (1 year)

Managed dedicated payroll, HR, and benefits client relationships in a regulated fintech environment, resolving payroll processing, tax filing, and benefits workflow issues. Led escalations with Engineering and Compliance and improved client self-service through advanced feature education.

Payroll Operations Tax Filings Benefits Administration Workflow Design Escalation Management SLA Management

Personal Banker I

Fifth Third Bank

Jan 2024 - Jan 2025 (1 year)

Provided retail banking support for account servicing and complex financial transactions while maintaining strict compliance with federal banking regulations. Built trusted client relationships through accurate, professional service and clear communication about financial solutions.

Customer Relationship Management Retail Banking & Compliance Risk Management Documentation Verification Customer Satisfaction

Account Manager, HCM & Payroll

ADP

Jan 2021 - Jan 2023 (2 years)

Served as primary point of contact for a high-volume portfolio of payroll and HR clients post-implementation, advising on payroll operations, benefits administration, and compliance best practices. Resolved technical escalations with internal teams to reduce turnaround time and improve user adoption of HCM platform features.

Benefits Administration Payroll Operations Service Delivery Management

Assistant Front Office Manager

Freehand Chicago

Jan 2019 - Jan 2021 (2 years)

Directed front office operations in a high-volume hospitality environment, overseeing staffing, scheduling, and service recovery to maintain guest satisfaction. Strengthened operational accuracy by enforcing accountability standards and improving front office coordination with housekeeping to speed room turnover.

Hospitality Operations Staff Scheduling Service Recovery Front Office Accuracy

Front Office Manager

Hyatt Regency McCormick Place

Jan 2015 - Jan 2019 (4 years)

Led and supervised front office operations for a large convention hotel, managing guest escalations, staffing, and daily execution of service protocols. Supported revenue growth through loyalty enrollments and consistently delivered service recovery aligned with Hyatt standards.

Front Desk Operations Service Recovery Staff Supervision Loyalty program support

Service Representative / Teller

BMO Harris Bank

Jan 2014 - Jan 2015 (1 year)

Handled customer transactions with strict adherence to banking regulations, internal controls, and risk-aware processing. Verified client documentation and recommended banking products to build trust and maintain 100% compliance.

Banking Compliance Internal Controls Documentation Verification