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A featured contribution from Leadership Perspectives: a curated forum reserved for leaders nominated by our subscribers and vetted by our Logistics Tech Outlook Advisory Board.


Jermaine Oldham, CIO and head of technology at Outdoor Cap Company, brings a wealth of industry experience to the table. He is well-versed in application development, database administration, product management, and infrastructure operations. Having started his career with the U.S. Air Force, Oldham brings over 25 years of experience in managing and leading technology teams at J.B. Hunt Transport, Peak 10, and Tempur Sealy. In his current role, he is responsible for across- the-board technology strategy and digital transformation of all business segments and personas, including employee, customer, and partner.
In an interview with CIOReview, Oldham sheds light on his strategic approach to cybersecurity and initiatives for seamless connectivity with users in the modern digital realm. He emphasizes the importance of aligning tech initiatives with business goals to ensure long-term success.
What are some of the current challenges and trends you see impacting the marketplace?
The significant trends and challenges in the marketplace revolve around digital transformation and cybersecurity, and technology can serve as a strategic enabler to drive business growth and prosperity. Businesses often find it daunting to recognize competitor strategies and figure out ways to connect technology with business needs to drive automation. The increasing reliance on the internet for transactions and B2B processes is another paramount concern. Threats are constantly evolving, and organizations must prioritize strengthening their security posture while thinking from their business’s vision and strategy perspective. Additionally, leveraging AI to enhance business operations and customer experience is an emerging trend that can be a strategic enabler for organizations.
"Threats are constantly evolving, and organizations must prioritize strengthening their security posture while thinking from their business’s vision and strategy perspective"
What, according to you, are some of the predicaments prevailing in the industry?
One of the concerns that keeps me up at night is the ever- evolving cybersecurity threat. We must stay vigilant to protect our company and customer data, as zero-day vulnerability and new attack vectors are emerging. At Outdoor Cap Company, we spent a lot of time understanding our risks, developed a comprehensive strategy, and adopted the National Institute of Science and Technology (NIST) cybersecurity framework that is now tied to our business priorities and goals.
Business continuity and disaster recovery are another concern. Whether a cyberattack, natural disaster, or man-made event, we need to ensure our business operations are not interrupted. We’ve invested in robust business continuity and disaster recovery plans to safeguard our operations in the face of potential disruptions.
Can you walk us through any project that you have been working on at Outdoor Cap Company and shed light on the strategies and technologies that you have implemented for its success?
One significant project we recently undertook at Outdoor Cap was strengthening our cybersecurity posture. We integrated security at the core of our technology strategy, aligning it with our business objectives. While developing the program, we first focused on understanding the business outcomes and drivers to ensure that our cybersecurity strategy was comprehensive, relevant, and effective. Once we got that clear, we assessed the risks and threats from a previous cybersecurity attack that affected our business for several weeks. This understanding served as the foundation for creating a baseline and adopting the NIST cybersecurity framework to map existing controls, identify vulnerabilities, and strengthen our defense posture.
We implemented an external penetration test and internal vulnerability scanning to assess our security measures. This provided valuable insights into our strengths and the gaps we needed to address. Based on this assessment, we created a target cybersecurity profile, setting the direction for our future security measures. With a clear vision of where we wanted to be, we developed a strategic three to five-year cybersecurity roadmap aligned with our new security framework.
Are there any specific technologies that you think might play a significant role in the near future?
The future of the marketplace revolves around how we can drive seamless connectivity and collaboration with users. One significant initiative we are planning to undertake is to develop a customer portal and streamline interactions with our customers to allow them to place orders directly through the site. Digitizing the process will streamline order-taking and managing product specifications, reducing the need for back- and-forth emails and calls.
Having our e-commerce technology serve as an interface to capture requirements upfront will enhance productivity and efficiency with our customer support. Additionally, we are focusing on enabling seamless connectivity through the implementation of PromoStandards. This will automate and standardize order processing, making it more efficient and accurate for both us and our customers. Modernizing internal platforms and applications will hold great potential to improve performance and usability, consequently resulting in a loyal customer base.
As a technology leader, what is your sage advice for budding professionals in the industry?
My advice to budding professionals in the tech industry is to never stop learning, even when in a leadership position. Continually developing skills and knowledge helps keep up with the rapidly evolving tech landscape. Embracing the opportunities to gain certifications and expertise in areas of interest will showcase our skills and the effective utilization of our time.
As tech professionals, it’s crucial to align our work with business objectives and focus on how our technology initiatives can empower the business, improve processes, and enhance the customer experience.