Kimberly Jacobson
Systems Analyst
28years of work
23years in operations
12years leading teams
8.3years average tenure
Overview
Technology and operations professional with experience spanning enterprise software consulting, financial operations, business systems, and technology delivery. Managed operational governance and structured tracking for complex fintech implementations and built documentation and control processes to improve reliability and follow-through. Developing practical expertise in generative and agentic AI, including an LLM-based personal finance coaching project.
Timeline
Senior Project Manager, Electronic Payments
·
Lead
Deluxe
·
Full-Time
Coordinated fintech implementation work across product, engineering, operations, infrastructure, and banking teams to keep requirements, dependencies, risks, and delivery details organized and visible. Established governance and tracking with structured documentation and reporting for multiple concurrent initiatives in a regulated environment. Translated technical information into operational actions, resolved discrepancies, and followed ownership through to completion using Jira, Smartsheet, and Microsoft 365-based tools.
Smartsheet
Jira
Purdue University
Bachelor's Degree ·
Information Systems Managament
VP Operations / Senior Project Manager
·
Head+
ClearSky Technologies
·
Full-Time
Managed operational and technology work across business functions by turning organizational needs into structured processes, systems, tracking, reporting, and executable plans. Collaborated with technical and business teams on system implementations, process improvements, documentation, and operational scalability. Used financial and operational analysis to troubleshoot issues, strengthen workflows, and keep recurring work organized.
Managing Partner / CFO, Operations & Technology Leader
·
Lead
TEAMabsolute
·
Full-Time
Co-led an enterprise software consulting company with responsibilities spanning finance, technology operations, business systems, internal controls, and day-to-day infrastructure. Maintained detailed asset and financial records and owned recurring operational processes including accounting, cash flow, forecasting, reporting, and compliance. Partnered with technical leadership on databases, enterprise systems, software implementations, and data center operations, including support for acquisitions, SOX-related compliance, commercialization, and organizational transition.
Projects
ClearLedger (AI personal finance coach)
Built an AI-powered personal finance coaching assistant using LLM-based transaction categorization and financial analysis. Added predictive modeling and stateful coaching logic to support ongoing guidance for user finances. Focused on practical AI reliability, evaluation, and responsible application in a personal finance context.
Technical skills
Python
SQL
AI/ML
LLM
ChatGPT
Copilot
AI Agents
RAG
Analytics
Power BI
Job preferences
- Work permits
- United States
- Employment type
- Full-Time
- Locations
- Chicago
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