Kevin Young

Initiator
DISC Type : Di

Vice President of Sales at Letter AI

Chicago, Illinois, United States

Overview

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.

Personality Overview

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.

Topics They Care 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.
Value-Based Selling
He believes sellers should focus on solving a buyer's problem rather than showcasing product features and differentiators, a core tenet of his sales philosophy.

Media Appearances

Kevin has no verified media appearances

Work History

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

Education

2004 - 2008
Education details unavailable from Iowa State University

More Information

Social Presence :

Prographics :

Exp : 17 Location : Chicago, Illinois, United States Job Level : Senior Designation : Vice President of Sales at Letter AI
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Insights For Selling To Kevin

During A Call Or A Meeting

DO's

  • Keep your pitch focused on the impact but insert some anecdotes into it
  • Refer to testimonials from well known people to highlight the value of your product
  • Focus on the big picture and the strategic value of your product

DONT's

  • Don’t keep repeating the same information, it could make them impatient
  • Don’t be too verbose or overly friendly; a little bit, however, is fine
  • Don't be unorganized, be prepared for the pitch

When Cold Calling

When Writing An Email

While Negotiating & Closing

    The secret to closing fast with Kevin is

  • Confidence in the product’s value is critical, followed by relationship and a sense of achievement.
  • Will you ever get a clear answer from Kevin

  • They will not hesitate to say no if they do not develop conviction.

Insights For Deal Planning

    How fast (or slow) will Kevin move?

  • If they develop confidence in your product and you, then they can make fast decisions.
  • Can Kevin take some risk or not?

  • If necessary, they have the ability to take risky decisions.

You And Kevin

Personality Compatibility


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