Rashad N. Lightsey in

Rashad N. Lightsey

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Regional VP, Enterprise Sales at Highspot
📍 Greater Chicago Area, United States

Rashad is a seasoned enterprise technology sales leader, currently serving as Regional VP of Enterprise Sales at Highspot. His expertise covers SaaS, AI solutions, and revenue enablement, with a history of leadership roles at Workday and TriNet. He holds a Bachelors degree from Indiana University and is described as a trusted, motivating mentor.

Based in the Illinois area, Rashad has spent a significant part of his career leading teams in Chicago. He is an alumnus of Indiana University, suggesting a connection to the region and its local culture.

Unique fact: While at Paychex, he helped lead the Chicago district to its first Conference qualification in the history of the office.

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Experience
18 Years
Current Role
Regional VP, Enterprise Sales
Job Level
Senior
Location
Greater Chicago Area, United States
Personality Overview

How Rashad shows up

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 Rashad cares about

AI in Sales
His professional focus includes "AI Solutions", and he has actively promoted events featuring AI capabilities in workforce planning, indicating a strong interest in its application.
Sales Leadership
Throughout his career, he has held leadership positions focused on building strong sales cultures centered on integrity, accountability, and mentorship to exceed goals.
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Career

Work history

6-2025
Regional VP, Enterprise Sales
Highspot
3-2021 - 6-2025
Regional Sales Director -Enterprise/ Financials & HCM
Workday
2-2018 - 3-2021
Regional Director of Sales
TriNet
12-2015 - 2-2018
Director of Sales, Technology
TriNet
5-2011 - 12-2015
District Sales Manager
PAYCHEX INC
In the press

Media appearances

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Education
Bachelor's degree
Indiana University
High School Diploma
Andrean High School
Social presence
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Behavioral profile

DISC profile (public)

DISC behavioral profile

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