Stephen Cheshire

Energizer
DISC Type : I

Chief Financial Officer at DGSF

Orange County, California, United States

Overview

Stephen Cheshire is a Chief Financial Officer with over 20 years of experience in asset management and corporate finance, notably contributing to one of the largest industrial real estate transactions in the US. His background includes a Bachelor of Arts from Concordia University Irvine. People he has worked with describe him as intelligent, responsible, and knowledgeable.

Beyond his corporate roles, Stephen demonstrates a strong commitment to community service, having earned a FireFighter 1 Certification. This practical, hands-on training complements his extensive background in business and finance, showcasing a multifaceted personality dedicated to both professional excellence and civic duty.

Unique fact: Stephen is a certified firefighter, a distinct qualification for a professional in the finance and real estate sector.

Personality Overview

Believer

Informal

Relationship Oriented

They are not always early adopters but can be pursuaded by leveraging strong relationships.  They are friendly, approachable and love to make new connections. They are really good at seeing what the long-term impacts of their decisions could be.

Topics They Care About

Real Estate Investment
Has over 20 years of experience in leading roles in asset management, overseeing portfolios of over 170 million square feet.
Corporate Finance
Currently serves as the Chief Financial Officer for DGSF, leveraging his extensive experience in fund and asset management.
Strategic Branding
As CFO of DGSF, he is involved with helping clients communicate their vision through strategy, storytelling, and design.

Media Appearances

Stephen has no verified media appearances

Work History

11-2019
Chief Financial Officer at DGSF
11-2017
CEO at Core Concepts Real Estate Group, Inc.
1-2020
Managing Partner at Waves Caribbean
1-2021
Managing Partner at Cheshire Worldwide, LLC
5-2015 - 11-2017
VP Fund Management at Global Logistic Properties (GLP)

Education

Bachelor of Arts; Bachelor of Arts from Concordia University Irvine
FireFighter 1 Certification from Santa Ana College

More Information

Social Presence :

Prographics :

Exp : 10 Location : Orange County, California, United States Job Level : Leadership Designation : Chief Financial Officer at DGSF
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Insights For Selling To Stephen

During A Call Or A Meeting

DO's

  • Use phrases like ‘people will love’, ‘massive impact’ etc.
  • Share some stories about how you you have helped people in similar positions succeed
  • Talk anecdotally about the customer experience that your product offers

DONT's

  • Don’t assume a yes just because they have not said no
  • Avoid ifs and buts, don’t talk too much about the risks etc.
  • Don’t be excessively objective, be a storyteller

When Cold Calling

When Writing An Email

While Negotiating & Closing

    The secret to closing fast with Stephen is

  • Relationship and rapport can play an important role, sometimes more than the other factors.
  • Will you ever get a clear answer from Stephen

  • They will probably never say no directly, you have to make that decision yourself.

Insights For Deal Planning

    How fast (or slow) will Stephen move?

  • They are not the quickest decision makers, their friendly attitude could be misleading.
  • Can Stephen take some risk or not?

  • They can accept limited risks, ones that they think will not impact them personally.

You And Stephen

Personality Compatibility


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