In this special edition of The Executive Outlook, we had the insightful opportunity to talk with Scott Brammer, Chief Information Security Officer (CISO) at RegEd. With decades of experience ranging from national defense to innovative startups, Scott brings a powerful voice to how cybersecurity must evolve alongside AI and digital transformation.
Scott shared that his journey began long before AI was the buzzword it is today. He recounted years of leadership roles across industries, growing teams and securing systems, all while focusing on one guiding principle: security must empower business, not block it. “Cybersecurity is not just about protection,” Scott said. “It’s about enabling growth and building trust.”
He explained that AI changes the threat landscape dramatically. Security must adapt quickly. “You can no longer rely on past frameworks alone,” he explained. “Every organization should assume AI tools are being used across their teams, sometimes unknowingly. That’s why training and governance matter more than ever.”
Scott added by sharing that companies need to move beyond just compliance checklists. “Compliance is the floor, not the ceiling. Real security lives above it.” He explained how in today’s world, cybersecurity is not an IT issue; it’s a business enabler. Companies that embrace this mindset grow faster and survive longer.
Watch the full conversation on YouTube by clicking the link below:
He spoke about the Office of the CISO as a place of strategic calm. “We sometimes call it the office of de-escalation. We try to stop fires before they start.” He further defined that the CISO’s role is often misunderstood. “We don’t just manage technology. We lead a culture. We build resilience.”
According to him, a CISO must think like a business leader first and a tech leader second. “You must speak the language of business. You must align strategic goals. You have to explain threats in terms your board and CEO can understand.”
He emphasized that trust, communication, and clarity are the cornerstones of effective cybersecurity leadership. “From the CEO to the help desk, security must be everyone’s responsibility.” Scott also shared how his role means managing across departments, becoming a translator between technical jargon and strategic intent.
He shared how his first 90 days at RegEd were shaped by listening, mapping the budget, and finding early wins. “The budget tells you where power lies—and where it doesn’t.” ‘Understanding budget allocations,’ he explained, ‘ helps identify ownership and control across tools and processes.’ “It’s a map of risk and opportunity. If your tools sit in someone else’s budget, you may not control them—yet you’re accountable for their security.”
Scott then added a leadership reminder: “If you see something broken in your first 90 days, fix it. Don’t wait. Waiting for day 91 is old thinking.”
For Scott, building a strong security team starts with people. “You need the right people in the right roles. Security teams are often small, underfunded, and overwhelmed. So, you need team members who are adaptable and empowered.
Scott Brammertalked about his approach to team dynamics: daily stand-ups, open communication, and shared emotional support. “We deal with alert fatigue. We need each other to stay sharp and sane.”
Prefer to listen on the go? Tune in to the full podcast episode on Spotify below:
“We’re the cavalry,” he added with a grin. “No one is coming to save us. We save ourselves.”
When hiring, Scott looks beyond technical skills. “Don’t overfocus on technical skills. Enthusiasm, responsibility, and curiosity go a long way.” He empowers new hires quickly: “Whether they’re an analyst or a director, I expect them to own their mission, represent our team in client meetings, and carry the torch forward.”
He elaborated, “If my people feel trusted, they’ll go further, faster. Trust breeds innovation.”
He emphasized that security leadership is about enabling, not micromanaging. “If you’re too busy doing the work yourself, you’re not leading, you’re lagging.”
Speaking about AI, Scott noted that many companies are unaware of how embedded AI already is in their workflows. “Start by knowing what AI tools your teams are using. Most don’t even realise how much AI is already inside their systems.”
He warned that blocking tools isn’t the answer. “Don’t just block everything. That only frustrates users. Train them instead.
“Tools like Microsoft Copilot and Adobe AI are powerful. But without guardrails, they can lead to serious data leaks.”
Scott explained that while DLP (Data Loss Prevention) tools help, people remain in the first line of defense. He encourages security leaders to actively participate in AI/ML committees: “Security needs to guide AI strategy. Otherwise, it becomes shadow IT.”
He offered a memorable analogy: “Think of it like giving a child scissors. AI is sharp and fast. But without rules, someone gets hurt.”
Scott also walked us through building a business-aligned security roadmap: “Start with your business goals. Understand your gaps. Look at previous roadmaps, budget constraints, and compliance pressures. Then build from there.”
He emphasized the importance of involving stakeholders early: “If the board doesn’t support your roadmap, it’s not going anywhere. Engage them. Bring data. Speak in their language.”
He added, “Roadmaps that are built in silos don’t survive in the real world. Security must be part of the product, the process, and the people.
He also recommended revisiting roadmaps quarterly. “You can’t set it and forget it. Security is a moving target. Your roadmap should evolve with it.”
When it came to regulatory change, Scott had a clear message: “Regulatory change always outruns preparation. So, build flexible systems and resilient teams.”
He recommended setting up alert systems, reading release notes, and participating in CISO networks to stay ahead. “The secret is flexible architecture. Microservices, containers, and DevOps maturity—these let you pivot when the rules change overnight.”
He shared an example: “When the SEC’s new rule dropped, most companies were shocked. But if you’d been tracking the discussions, the warning signs were there. We had time to act.”
Scott believes that security culture should be embedded, not imposed. “People support what they help build. Invite them into the process. Make them feel responsible, not restricted.”
Scott Brammer stressed the importance of psychological safety on security teams. “It’s okay to speak up, admit mistakes, and ask for help. That’s how we stay ahead of threats. That’s how we grow.”
He added that cybersecurity should be part of onboarding, not just once a year training. “You want people to think, ‘Security is my job too.’ That mindset changes everything.
In his view, leadership in cybersecurity is a long-term commitment. “It’s not just about fixing today’s vulnerabilities. It’s about building tomorrow’s resilience.”
He pointed out that mentorship is another overlooked component of a healthy cyber organization. “You don’t just grow systems. You grow, people. The next generation of cyber leaders is watching how we will show up today.”
Scott also shared how storytelling is a powerful tool for change. “If you want the business to care about cyber, don’t show them numbers; tell them stories. Talk about the customer who almost lost their data or the system that failed just in time. People connect with stories.”
He believes that the real test of a cybersecurity team is not how fast they respond but how well they prepare. “If you’re prepared, the fire drill becomes routine. If you’re not, it will become a disaster.”
Scott believes in giving his teams space to grow: “Security is a partnership. If you treat it like a blocker, it will feel like a drug. But if you treat it like a coach, it’ll win you championships.”
He concluded with a reminder for all business leaders: “Cybersecurity is not about saying no. It’s about saying yes, safely.”
In Scott Brammer, we see more than a security leader. We see a partner in progress, a business builder, and a guide for navigating complexity with courage and clarity.
Stay tuned for more inspiring stories in The Executive Outlook.
Editor Bio
I’m Isha Taneja, serving as the Editor-in-Chief at "The Executive Outlook." Here, I interview industry leaders to share their personal opinions and provide valuable insights to the industry. Additionally, I am the CEO of Complere Infosystem, where I work with data to help businesses make smart decisions. Based in India, I leverage the latest technology to transform complex data into simple and actionable insights, ensuring companies utilize their data effectively.
In my free time, I enjoy writing blog posts to share my knowledge, aiming to make complex topics easy to understand for everyone.
