Skye Snayd in

Skye Snayd

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Senior Mid-Market Account Executive at HubSpot
📍 Chicago, Illinois, United States

Skye Snayd is the Founder and CEO of Vanguard Prospecting, where he specializes in building high-powered outbound sales programs. A graduate of Florida State University, he has a diverse industry background and is also an Executive Officer in the Army National Guard, applying military discipline to his business strategies.

Outside of his entrepreneurial ventures, Skye is deeply committed to his military service as an Infantry Officer. He often speaks about translating the leadership principles and discipline from his time as a Platoon Leader and Executive Officer into his approach to building teams and driving business results.

Skye effectively balances his duties as a startup CEO with his ongoing leadership responsibilities in the Army National Guard.

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Experience
9 Years
Current Role
Senior Mid-Market Account Executive
Job Level
Middle
Location
Chicago, Illinois, United States
Personality Overview

How Skye 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 Skye cares about

Outbound Sales Programs
His company, Vanguard Prospecting, is dedicated to creating and implementing revenue-generating outbound sales strategies for a diverse range of B2B clients.
Military Leadership
As an Executive Officer in the Army National Guard, he frequently discusses applying military leadership principles to his role as a CEO.
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Career

Work history

4-2026
Senior Mid-Market Account Executive
HubSpot
4-2025 - 3-2026
Mid Market Account Executive II
HubSpot
6-2022 - 4-2025
Co-Founder & CEO
Skyeline Consulting
7-2020 - 6-2022
Co-Founder & CEO
Vanguard Prospecting
6-2019 - 7-2020
Account Director
FullFunnel
In the press

Media appearances

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Education
Bachelor of Science (B.S.)
Florida State University
Education details unavailable
Mercersburg Academy
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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