Gregory Siefkin

Trailblazer
DISC Type : DI

Sr. Engagement Manager, North America at Rimini Street

Los Angeles, California, United States

Overview

Gregory is a proven technology sales leader with 25 years of experience specializing in AI, SaaS, and enterprise software. Currently a Sr. Engagement Manager at Rimini Street, colleagues describe him as having deep technical expertise, business acumen, and a client-focused approach. He studied Biology at California State University, Long Beach.

An upbeat and personable networker, Gregory enjoys embracing new technologies and working with cross-functional teams on complex projects. His recommendations highlight his ability to listen to client needs and deliver creative, effective solutions.

He is a recipient of the MVP Award for his success in closing new business deals while simultaneously helping his colleagues succeed.

Personality Overview

Friendly But Fast

Values Relationships

Assertive

A combination of speed and relationship gets the best response from them.  They are more likely to accept new and exciting technologies. They are not against taking risks and can make tough decisions when required.


Topics They Care About

AI Enablement
His background includes roles as a Sr. Growth Consultant in AI Enablement and extensive work with AI model training and conversational AI.
Conversation Intelligence
He previously led North American enterprise sales for Call Journey CI, a global leader specializing in conversation intelligence and voice analytics.
Enterprise Software
His current role at Rimini Street involves providing solutions for Oracle, SAP, and VMware software, reflecting a deep industry knowledge.

Media Appearances

Gregory Siefkin - Sr. Engagement Manager, North America at Rimini Street. Featured in The Org

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Work History

10-2025
Sr. Engagement Manager, North America at Rimini Street
12-2024 - 10-2025
Sr. Growth Consultant- AI Enablement at Invisible Technologies
10-2023 - 12-2024
Director, Enterprise Sales - North America, Conversation Intelligence AI at Call Journey CI
8-2022 - 10-2023
Sr Strategic Client Partner - Conversational AI and Analytics at LivePerson
4-2021 - 10-2023
Senior Voice Sales Director - Contact Center Analytics/AI (VoiceBase) at LivePerson

Education

1991 - 1996
Biology from California State University, Long Beach

More Information

Social Presence :

Prographics :

Exp : 6 Location : Los Angeles, California, United States Job Level : Middle Designation : Sr. Engagement Manager, North America at Rimini Street
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Insights For Selling To Gregory

During A Call Or A Meeting

DO's

  • Display high self-confidence and expect them to have a strong personality.
  • Give them control of the sales process
  • Address your competition clearly and confidently

DONT's

  • Don't make any commitments that you might not be able to fulfill
  • Don’t hesitate from asking questions or pushing them, but take a friendly approach
  • Don’t hesitate from asking them how they truly feel about your product

When Cold Calling

When Writing An Email

While Negotiating & Closing

    The secret to closing fast with Gregory is

  • Relationship and product conviction matter equally, followed by a sense of achievement.
  • Will you ever get a clear answer from Gregory

  • If they are not convinced, they will say no though in a friendly way.

Insights For Deal Planning

    How fast (or slow) will Gregory move?

  • They can make decisions quickly if they develop trust in you and conviction in the product.
  • Can Gregory take some risk or not?

  • If necessary, they will be ready to take risks.

You And Gregory

Personality Compatibility


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