Tobias Caldwell

Observer
DISC Type : ic

Director Security Engineering at Gap Inc.

San Francisco, California, United States

Overview

With over 30 years of experience at Gap Inc. , Tobias has progressed from a network engineer to the Director of Security Engineering. He leads DevSecOps and Infrastructure Security, leveraging his deep expertise in cloud security, network architecture, and security automation. He holds a Cisco CCNP certification and has passed the CCIE written exam.

Personality Overview

Value Driven

Assertive

Curious

They are generally strong communicators and are not easy to convince.  They can sound friendly and charming but can quickly change gears to become inquisitive and probing. They often ask many questions and rely heavily on information and documentation.

Topics They Care About

DevSecOps Leadership
He leads the DevSecOps and Infrastructure Security functions for Gap Inc. , focusing on integrating a security-first mindset into development and operations teams.
Cloud & Network Security
His career has focused on building secure platforms, from redesigning European networks to implementing security automation in cloud and hybrid environments.
Professional Certification
He credits his career progression to earning certifications like the Cisco CCNA and CCNP, which enabled him to take on leadership roles in engineering projects.

Media Appearances

Tobias has no verified media appearances

Work History

8-2024
Director Security Engineering at Gap Inc.
6-2021 - 8-2024
Senior Manager - DevSecOps & Infrastructure Security at Gap Inc.
10-2018 - 8-2024
Lead Cloud Security Engineer at Gap Inc.
3-2016 - 10-2018
Lead Network Security Engineer at Gap Inc.
3-2001 - 3-2016
Network Engineer at Gap Inc.

Education

1991 - 1994
Education details unavailable from Mid Warwickshire College

More Information

Social Presence :

Prographics :

Exp : 28 Location : San Francisco, California, United States Job Level : Mid-senior Designation : Director Security Engineering at Gap Inc.
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Insights For Selling To Tobias

During A Call Or A Meeting

DO's

  • Share testimonials from known people and give multiple examples of product value
  • Be prepared for a lot of questions, answer them objectively
  • Help them realize that there is no personal risk in making this decision

DONT's

  • Avoid making offhand commitments
  • Don’t try to rush them into a decision, provide all necessary information first
  • Don’t be too objective but make sure to pad your storytelling with data points

When Cold Calling

When Writing An Email

While Negotiating & Closing

    The secret to closing fast with Tobias is

  • Clear proof of product value matters to them, followed by others' testimonials and rapport.
  • Will you ever get a clear answer from Tobias

  • They are practical yet friendly, don’t expect a clear no very often.

Insights For Deal Planning

    How fast (or slow) will Tobias move?

  • They like to analyze well and can take their time to reach any decisions.
  • Can Tobias take some risk or not?

  • They systematically evaluate all decisions and are unlikely to take many risks.

You And Tobias

Personality Compatibility


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