Derrick Whalen, CIO.D

Questioner
DISC Type : c

Director of Information Technology at Seaboard Armour Transportation and Logistics

Halifax, Nova Scotia, Canada

Overview

Derrick Whalen is a strategic IT leader with over 25 years of experience in cybersecurity, IT governance, and cloud platform modernization. He leads digital transformation and data integration strategies, holding a CIO. D™️ certification. He is an alumnus of the University of New Brunswick and St. Thomas University.

He is passionate about leadership development and community building among IT professionals. Derrick is the Atlantic Chapter President for the CIO Association of Canada and serves as a Leadership Communication Coach, helping professionals become more confident and influential leaders through specialized training.

For over two decades, Derrick has simultaneously pursued a career in IT leadership and a separate role as a professional leadership communication coach.

Personality Overview

Not Easily Convinced

Cautious & Analytical

Price-Sensitive

They generally do not appreciate an overfriendly approach and prefer to stay to-the-point.  While they don't hesitate to ask questions, they are generally risk-averse and tend to be late adopters. They prefer to fully evaluate every situation.

Topics They Care About

IT Leadership Development
As Atlantic Chapter President of the CIOCAN and a coach at PowerTalk Communications, he actively mentors the next generation of IT leaders and fosters peer collaboration.
Cybersecurity Resilience
A core focus in his professional roles, where he is responsible for developing and leading cybersecurity strategy.
Cloud & Data Integration
He has led major IT modernization projects, including a Microsoft Azure/Databricks data integration platform to enhance operational efficiency and data-driven decision making.

Media Appearances

Derrick has no verified media appearances

Work History

12-2025
Director of Information Technology at Seaboard Armour Transportation and Logistics
2-2019 - 12-2025
Director, Information & Technology Services at Port of Halifax
7-2011 - 2-2019
Leadership Communication Coach at Power Talk Communications
1-2011 - 10-2018
IT Strategy Consultant at PowerTalk Communications
12-2009 - 4-2011
Vice President, Information Technology and Operational Risk at ING Real Estate Canada

Education

1993 - 1995
Education from University of New Brunswick
Arts from St. Thomas University (CA)

More Information

Social Presence :

Prographics :

Exp : 30 Location : Halifax, Nova Scotia, Canada Job Level : Mid-senior Designation : Director of Information Technology at Seaboard Armour Transportation and Logistics
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Insights For Selling To Derrick

During A Call Or A Meeting

DO's

  • Emphasize on objective proof of ROI, help them do a thorough evaluation
  • Keep some extra margin in hand as they will likely negotiate the pricing
  • If you have a lower priced product compared to the competition, call out the same

DONT's

  • Avoid phrases like ‘do not worry about’, ‘no one compares to’ etc.
  • Don’t overhype the product/pitch, keep it measured
  • Don’t try to be too friendly or informal with them

When Cold Calling

When Writing An Email

While Negotiating & Closing

    The secret to closing fast with Derrick is

  • Ensuring that the product delivers ROI, cost-effective pricing and process compliance are very important for them.
  • Will you ever get a clear answer from Derrick

  • It doesn’t come naturally to them but they can say no if they are not convinced.

Insights For Deal Planning

    How fast (or slow) will Derrick move?

  • If they have the information that they need, they can move fast at making their decisions.
  • Can Derrick take some risk or not?

  • If they believe that they have analyzed the situation well, they can take a little risk.

You And Derrick

Personality Compatibility


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