Stephanie Leonard in

Stephanie Leonard

Commander · DISC type D
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

How Stephanie shows up

Impact-Driven
Strong-Willed
Decisive

They are less concerned about the product and more about its potential impact. They like to stay in control of the negotiation or defining of the terms. They prefer to move quickly, and expect the same from others.

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

No media yetWe could not find public media appearances for this person.
Education
1993 - 1995
Business Marketing
Howard University
Social presence
in
Behavioral profile

DISC profile (public)

D

Dominance (D)

Dominance (D) reflects how goal and task oriented a person is, and their ability to accomplish results irrespective of how demanding the circumstances might be. Those scoring high tend to be motivated by winning, competition, and success.

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