Jason Sinyor

Commander
DISC Type : D

Head of Sales at Workwize

New York, New York, United States

Overview

Jason Sinyor is a results-oriented sales leader with a track record of scaling high-performing teams for SaaS companies, driving revenue from $5M to over $50M. An alumnus of the University of Maryland, he is praised for his entrepreneurial leadership, analytical insight, and team-oriented approach.

He is passionate about building strong, authentic team cultures where people feel connected, respected, and empowered. Jason has a noted interest in cross-cultural business dynamics, particularly the fusion of Dutch and American professional styles to create unique advantages.

He was a featured speaker at a NAF-biz networking event, discussing how to combine Dutch and American cultures to unlock business "superpowers".

Personality Overview

Decisive

Risk-Taker

Impact-Driven

They prefer to move quickly, and expect the same from others.  They put a lot of effort into ensuring personal success. They are less concerned about the product and more about its potential impact.

Topics They Care About

Scaling Sales Teams
His career focus is building and scaling world-class sales organizations for high-growth SaaS companies, a topic he frequently posts about while actively hiring new leaders.
SaaS Growth
He has a proven history of expanding revenue for SaaS businesses and is currently focused on Workwize's explosive growth, having tripled revenue in the past year.
Authentic Team Culture
He emphasizes building a culture that thrives on winning, ownership, and authenticity, where team members feel genuinely connected, respected, and can learn from each other.

Media Appearances

Jason has no verified media appearances

Work History

1-2025
Head of Sales at Workwize
9-2023 - 1-2025
Vice President Enterprise Sales- East at TeamViewer
12-2019 - 8-2023
Director of Global Sales at Diligent Corporation
5-2017 - 12-2019
Director of Global Sales Development at Diligent Corporation
5-2015 - 5-2017
Manager, Inside Sales at Tracx

Education

Bachelor’s Degree from University of Maryland - Robert H. Smith School of Business

More Information

Social Presence :

Prographics :

Exp : 14 Location : New York, New York, United States Job Level : Mid-senior Designation : Head of Sales at Workwize
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Insights For Selling To Jason

During A Call Or A Meeting

DO's

  • Help them weigh the risks by sharing objective proof points without becoming too analytical
  • Hold your ground without indulging in one-upmanship
  • Objectively showcase the impact that your product creates

DONT's

  • Don’t focus on process and rules, give the impression of being a ‘gets it done’ person
  • Don’t be in a rush to invite them for a social meet and greet
  • Don’t take too much time in sending them information if they ask for any

When Cold Calling

When Writing An Email

While Negotiating & Closing

    The secret to closing fast with Jason is

  • Conviction around the impact matters the most to them, followed by a sense of achievement and ROI.
  • Will you ever get a clear answer from Jason

  • If they are not convinced, they will say no without any hesitation.

Insights For Deal Planning

    How fast (or slow) will Jason move?

  • If convinced, they can reach decisions quite fast.
  • Can Jason take some risk or not?

  • They do not shy away from taking risks, but can be quite binary about them.

You And Jason

Personality Compatibility


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