Enterprise Product · Digital Transformation · AI Strategy

Jessica
Greenwald

I build the platforms enterprises run on, and lead the teams that ship them.

16+
Years / Enterprise Leadership
5,000+
Daily Platform Users
~$600K
Annual Operational Savings
4
Roles / Recruiter → Director

About

Strategy is only real once people use it.

Now
Director of Driver Systems
C.R. England · Salt Lake City

Leads
Product Management
Business Analysis
UX & Product Operations

Partners with
Operations · Safety · HR
Payroll · Recruiting · IT
Executive Leadership

For sixteen years I've built the systems a national enterprise runs on, starting on the front line and rising to lead Product, Business Analysis, and UX. My teams design and scale the mobile and web platforms that more than 5,000 people depend on every day to do their jobs.

What I care about most is the moment strategy becomes something real: a roadmap that actually ships, a manual process that disappears, a workforce that adopts a tool because it genuinely helps. Lately that means putting AI to work, not as a headline but as a shift in how quickly intent becomes execution.

The technology keeps advancing. The work still comes down to people.

Signature Transformations

Platforms built, launched, and adopted at scale.

01

Driver 360 (D360)

Flagship enterprise engagement platform that unified fragmented workforce data into a single operational view for 5,000+ daily users.

02

Enterprise AI Adoption

Introduced applied and generative-AI use cases across product and operations, positioning the organization as an early adopter.

03

Mobile Platform Redesign

Re-architected the primary enterprise workforce application (Driver Toolbox) for usability, self-service, and adoption.

04

Unified Communications

Led a company-wide RingCentral migration from legacy telephony to a scalable, reliable cloud communications platform.

05

Enterprise Learning & Coaching

Established an LMS and department-based coaching system that standardized training and performance workflows organization-wide.

06

Workflow Automation

Directed an automation and platform-consolidation portfolio contributing to approximately $600K in annual operational savings.

Driver Chat Document Upload Portal Safety Platform Modernization Enterprise Communications Multi-Year Roadmaps

Capabilities

How I lead.

/Enterprise Product Strategy
/AI Strategy & Adoption
/Digital Transformation
/Multi-Year Product Roadmaps
/Enterprise Software & Platforms
/Business Systems Modernization
/Product Operations
/Mobile Platform Strategy
/Change Management
/Cross-Functional Leadership
/Executive Stakeholder Alignment
/Workflow Automation

Certifications

Credentials.

Certified Pega Business Architect (CPBA)Pearson VUE · 2023
Advanced Certified Scrum Product Owner (A-CSPO)Scrum Alliance · 2019
Certified Scrum Product Owner (CSPO)Scrum Alliance · 2017