Jack Rutstein

Enthusiast
DISC Type : i

Account Executive at Subject

United States

Overview

Jack leads Midwest partnerships at Subject AI, leveraging his sales background to replace legacy educational tools with engaging, AI-powered curricula. A DePauw University graduate, his career has been built on driving growth and impact in the technology sector, including his time at Paradox through its acquisition by Workday.

Outside of his professional role, Jack is a passionate Chicago sports fan, specifically mentioning his support for the Cubs. He enjoys the community aspect of sports, hosting tailgate events for college football games. He also dedicates time to mentoring, offering career coaching as a side project.

As a side gig, Jack provides career coaching to college students, sharing his professional insights to help them get noticed by companies.

Personality Overview

Consensus Focused

Amiable & Agreeable

Story Driven

Unlike D or C types, they are convinced more by stories and testimonials.  They are more about building relationships than just cutting deals. They agree with others often, so exercise caution when relying on their word.

Topics They Care About

AI in Education
Focuses on transforming education by partnering with school districts to implement cinematic, AI-powered curricula.
Career Mentorship
Passionate about guiding the next generation, offering career coaching as a side gig to help college students succeed.
Midwest Partnerships
Leads the entire partnership and sales cycle in the Midwest, building relationships with educators in states like Michigan and Wisconsin.

Media Appearances

Jack has no verified media appearances

Work History

9-2025
Account Executive at Subject
2-2025 - 8-2025
BDR II at Paradox by Workday at Paradox
5-2024 - 2-2025
BDR I at Paradox at Paradox
5-2023 - 5-2024
BDR at Paradox
12-2022 - 5-2023
Group and Premium Ticket Sales Intern at Pacers Sports & Entertainment

Education

2020 - 2024
Bachelor's degree from DePauw University
2016 - 2020
Education details unavailable from Evanston Township High School (ETHS)

More Information

Social Presence :

Prographics :

Exp : 3 Location : United States Job Level : Junior Designation : Account Executive at Subject
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Insights For Selling To Jack

During A Call Or A Meeting

DO's

  • Maintain high, positive energy and convey confidence
  • Give them the opportunity to lead the conversation where possible
  • Speak from experience about success that the product has seen with other customers

DONT's

  • Don’t ask too many questions in one go, weave them into the flow
  • Don’t be excessively objective, be like a storyteller with them
  • Don’t be too formal with them, they trust informality more

When Cold Calling

When Writing An Email

While Negotiating & Closing

    The secret to closing fast with Jack is

  • Relationships and rapport matter to them, but so does the value of the product.
  • Will you ever get a clear answer from Jack

  • They probably won't say no directly.


Insights For Deal Planning

    How fast (or slow) will Jack move?

  • They are not the ones to make fast decisions, even while they stay committed.
  • Can Jack take some risk or not?

  • If it seems really necessary, they can take small risks.

You And Jack

Personality Compatibility


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