Kevin Young in

Kevin Young

Initiator · DISC type Di
Vice President of Sales at Letter AI
📍 Chicago, Illinois, United States

Kevin Young is the VP of Sales at Letter AI and a GTM Advisor with extensive experience in B2B tech sales leadership. People who have worked with him often describe him as genuine, thoughtful, empathetic, and authentic. He emphasizes a candid, first-principles approach to building and leading sales teams.

Outside of his professional life, Kevin is a fan of American football and the musician Hank Williams Jr. He has expressed a strong personal value in working with tangible, purposeful products that have a real-world impact, moving away from what he describes as just selling "internet toys".

He champions an "anti-playbook playbook" philosophy, believing that sales teams should think from first principles rather than relying on overly rigid, repeatable processes.

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Experience
17 Years
Current Role
Vice President of Sales
Job Level
Senior
Location
Chicago, Illinois, United States
Personality Overview

How Kevin shows up

Conviction Driven
Impact-Oriented
Risk-Accepting

They respond well to objective pitches but also attach some value to relationships. They measure a product on its merit but can be influenced by strong testimonials. They usually prefer to drive the conversation.

Priorities

Topics Kevin cares about

GTM Strategy
Serves as a GTM Advisor and has a proven track record of driving go-to-market success across sales and marketing teams at multiple tech companies.
Rethinking Sales Playbooks
He advocates for an "anti-playbook" approach, encouraging sales teams to think from first principles rather than over-relying on rigid, repeatable methods, as discussed on a recent podcast.
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Career

Work history

2-2026
Vice President of Sales
Letter AI
7-2025 - 1-2026
Area Vice President
LVT (LiveView Technologies)
8-2024 - 7-2025
Regional Director - CRED
LVT (LiveView Technologies)
9-2023 - 8-2024
Vice President of Sales
UserEvidence
2-2023 - 9-2023
Head of Sales
Metadata
In the press

Media appearances

No media yetWe could not find public media appearances for this person.
Education
2004 - 2008
Education details unavailable
Iowa State 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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