Jessica Greenwald | Business Transformation Executive

Career Story

From frontline execution to enterprise transformation.

My career started in recruiting and grew through performance, ownership, and a willingness to solve problems that did not yet have a playbook. I became a trusted subject matter expert, transitioned into IT, and advanced into product and technology leadership by bridging business needs with scalable technology solutions.

I have led initiatives across recruiting, onboarding, communications, learning systems, workflow automation, mobile applications, CRM modernization, AI adoption, and nationwide training. My strength is turning messy operational problems into clear, usable, scalable solutions.

Leadership Brand

The person organizations trust when work needs to change.

Business + Technology Bridge

Translate complex operational needs into practical product strategy, requirements, workflows, and adoption plans that both executives and engineers understand.

Transformation at Scale

Lead cross-functional programs impacting thousands of users, nationwide teams, and critical business systems without losing sight of the people doing the work.

People-Centered Change

Build trust with executives, managers, frontline employees, and technical teams to make change actually stick — not just launch.

Sanitized Case Studies

Selected Transformation Work

These examples are intentionally summarized to protect proprietary systems, internal screenshots, confidential business data, and active operations.

Mission-Critical Mobile Platform

Challenge: Thousands of users needed a reliable digital hub for daily work, communications, payroll visibility, and compliance.

Approach: Led product strategy, stakeholder alignment, roadmap prioritization, adoption support, and ongoing enhancements.

Impact: Supported 5,000+ daily users with a critical operational tool.

Workflow Automation

Challenge: High-volume document processes created manual work, cost, delays, and limited visibility.

Approach: Partnered with business and technical teams to digitize workflows, improve routing, and reduce repetitive manual steps.

Impact: Generated approximately $600K in annual operational savings.

Custom CRM Modernization

Challenge: Existing platforms created cost and flexibility concerns for evolving business needs.

Approach: Helped evaluate platform strategy, move away from costly legacy systems, and support custom CRM development.

Impact: Improved ownership, scalability, and alignment between business process and technology.

Recruiting Operations Transformation

Challenge: Large recruiting teams needed consistent training, process design, compliance support, and scalable programs.

Approach: Managed programs impacting approximately 200 recruiters and supported operations hiring roughly 250 people per week.

Impact: Built repeatable processes, training programs, and specialized initiatives across high-volume recruiting operations.

AI Adoption & Enablement

Challenge: Teams needed to understand how to use AI responsibly without confusing prototypes with production-ready solutions.

Approach: Led AI enablement, training, documentation, and productivity use cases focused on practical business value.

Impact: Improved speed, documentation quality, business analysis, and internal enablement.

Public Mobile App Launch

Challenge: Future CDL holders needed a simple study tool to prepare for permit testing.

Approach: Partnered with executive leadership to build and launch CDL FastPass as a standalone public mobile application.

Impact: Brought an app from concept to public app stores.

Core Strengths

Built for messy, cross-functional problems.

Enterprise Applications Mobile Applications AI Adoption & Enablement Workflow Automation CRM Strategy Learning Systems Communications Platforms Training & Change Management Executive Stakeholder Management Business Transformation Product Strategy Digital Transformation

Open to 100% Remote Roles

Seeking mission-aligned product, business systems, digital transformation, and enterprise technology leadership roles.

Best fit: Director of Product, Director of Business Systems, Director of Enterprise Applications, Director of Digital Transformation, or equivalent senior IC or leadership roles.

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