Jason Wolfson

Captain
DISC Type : DS

Vice President, Product Marketing & Enablement at Skai

San Mateo, California, United States

Overview

Jason is the Vice President of Product Marketing & Enablement at Skai, specializing in go-to-market strategies that accelerate revenue growth. A graduate of Penn State University, he is described by colleagues as a strategic, dedicated, and tenacious marketing expert with a proven ability to lead teams and execute tactically.

Outside of his marketing career, Jason is a passionate and intricate LEGO builder. He has created complex models of science-fiction icons like the Eagle Transporter from "Space: 1999" and characters like Gonzo, viewing the hobby as a profound learning experience and a bridge between personal interests and creative expression.

He has been featured in BrickJournal magazine for his elaborate LEGO creations, sharing his building process and inspiration.

Personality Overview

Consummate Professional

Dynamic But Sincere

Output-Driven

They are very professional in their approach and can weigh multiple perspectives together.  They exhibit a rare combination of being result-oriented but patient at the same time. They might take some time to make their mind up but once they do, they don't change it easily.

Topics They Care About

Commerce Media Strategy
Writes and speaks extensively on the future of retail and commerce media, focusing on programmatic advertising and navigating the evolving, AI-driven buyer journey.
Go-to-Market Leadership
His professional headline and roles are centered on leading revenue teams and bringing products to market "better, smarter & faster. "
LEGO Sculpting
An avid LEGO builder featured in publications for his complex science-fiction and fantasy models, which he views as a way to connect passion with learning.

Media Appearances

Jason has no verified media appearances

Work History

11-2024
Vice President, Product Marketing & Enablement at Skai
10-2023 - 11-2024
Senior Director, Sales Enablement at Samba TV
6-2022 - 10-2023
Director Sales Enablement at Samba TV
6-2021 - 5-2022
Director of Product Marketing at Samba TV
8-2020 - 6-2021
Vice President Product Marketing at Piano

Education

BS from Penn State University

More Information

Social Presence :

Prographics :

Exp : 8 Location : San Mateo, California, United States Job Level : Senior Designation : Vice President, Product Marketing & Enablement at Skai
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Insights For Selling To Jason

During A Call Or A Meeting

DO's

  • Use phrases like 'your team deserves', 'best in class' etc.
  • Come across as a trustworthy professional and be respectful, they usually know their game
  • Stick to your standard pitch and qualifying script, don't try to wing it

DONT's

  • Don't take their patience for granted, avoid long-winding sermons
  • Don't get into pricing discussions early on, steer conversation towards proven results
  • Don't shy away from asking hard questions, but be extra polite

When Cold Calling

When Writing An Email

While Negotiating & Closing

    The secret to closing fast with Jason is

  • Strong proof of impact and their conviction will matter the most, but they wouldn't want to act unilaterally either
  • Will you ever get a clear answer from Jason

  • They will say no if they are not convinced but you will have to prompt them.

Insights For Deal Planning

    How fast (or slow) will Jason move?

  • They will want to understand things well but can move fast once they have a clear picture.
  • Can Jason take some risk or not?

  • They have good risk tolerance but are likely to think it through once or twice.

You And Jason

Personality Compatibility


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