Stephanie Leonard in

Stephanie Leonard

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Consultant - Senior Subject Matter Expert SMR - UKG Data Integration at KIPP NYC
📍 Bowie, Maryland, United States

Stephanie Leonard is the Director of Contingent Workforce Solutions at Upwork, specializing in vendor management and human capital processes. She has a background in operations, including P&L responsibilities, and holds a degree in Business Marketing from Howard University. People who have worked with her describe her as a dedicated, efficient, and innovative leader.

Stephanie shows a strong interest in professional networking within her industry, actively participating in events and engaging with connections from organizations like ClubVMSA to stay current on workforce trends.

She once implemented a Vendor Management System to manage over $500 million in staff augmentation and Statement of Work spend.

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Experience
19 Years
Current Role
Consultant - Senior Subject Matter Expert SMR - UKG Data Integration
Location
Bowie, Maryland, United States
Personality Overview

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Communication Style
Decision Approach
Work Preference

Behavioral traits and communication patterns that shape how this person evaluates opportunities, builds trust, and makes decisions in professional settings.

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Priorities

Topics Stephanie cares about

Contingent Workforce
As the Director of Contingent Workforce Solutions at Upwork, this is her core area of expertise, focusing on strategy for non-permanent staff.
Vendor Management
A self-described expert, she has deep experience implementing and managing large-scale Vendor Management Systems (VMS) to oversee significant company spend.
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Career

Work history

12-2024 - 5-2025
Consultant - Senior Subject Matter Expert SMR - UKG Data Integration
KIPP NYC
5-2021 - 4-2024
Director Contingent Workforce Solutions
Upwork
7-2018 - 9-2020
Manager Workforce Planning
CareFirst BlueCross BlueShield
2-2014 - 7-2018
Manager Workforce Strategy & Management
CareFirst BlueCross BlueShield
10-2012 - 2-2014
Business Project Manager/HR Manager
CareFirst BlueCross BlueShield
In the press

Media appearances

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Education
1993 - 1995
Business Marketing
Howard University
Social presence
in
Behavioral profile

DISC profile (public)

DISC behavioral profile

Dominance, influence, steadiness, and calculativeness scores with guidance on how this person prefers to communicate and decide.

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