CISOs want to be on boards. Veteran tech executive Roosevelt Giles wants to help them get there.
Four years ago, Giles founded a program aimed at helping C-suite executives and senior leaders— including Chief Information Security Officers—secure board appointments, positioning them as key contributors to organizational growth and strategic direction.
“I use an analogy that the board represents the Supreme Court of stakeholder capitalism,” said Giles, the Chairman of Endpoint Ventures and President of Stakeholder Impact Foundation, Inc.
“Just like a Supreme Court ruling is the law of the land, so is a board ruling the law of the land on strategic issues in that company. The board hires the CEO, and it is the board that gives the CEO the level of authority. So that’s why I say the board is the epicenter of an organization.”
For a CISO, sitting on a private, small cap, midcap or Fortune 500 board offers a potent combination of prestige and remuneration – anywhere from $100,000 to $400,000 per appointment, Giles said. But to be an effective board member, it’s essential to have a servant leader mindset, and the ability to walk away, he added.
“On that board, you also are the voice of the voiceless,” he said. “All of those suppliers, community non-profits, company employees who are out there showing up to work every day and making $10 to $15 an hour depend on you to make the right decision. You can’t take that responsibility lightly. If you’re doing it for the money, you won’t last.”
What makes someone attractive as a board member is being a cultural fit, strategic, insightful, and with a diversity of experiences, Giles said. But while CISOs must understand the impact of technology and how breaches would impact the business, “they do not have to be a genius on financials to sit on a board,” he said.
CISOs need to scan the horizons to see what boards they would like to sit on where they could add the most value, Giles said.
“Don’t outsource this responsibility—take charge of it yourself,” he said. “Conduct the analysis and identify the companies that can benefit from what you bring to the table that they need by enhancing their total shareholder returns and earnings per share.”
Giles is the son of a sharecropper whose parents believed in the power of education. With dual degrees in computer science and business administration, he has built and run technology companies for some 40 years.
When he was fresh out of college, working as a programmer, a mentor took a liking to him and arranged that he sit in on board meetings.
“There I witnessed the power and the influence of the people who sit around the table and how they interact with management, along with the impact on all stakeholders,” he said.
After growing and building companies himself, Giles has been asked to sit on multiple boards, beginning at age 31 – then about half the average age of other board members.
“It changed my life,” he said. “I went on to other boards, because once you get on one board, that gets telegraphed.
“It is much more difficult to get the interview than it is to get that first board seat. But once you get that first board seat, you’re in the club, and the majority of new board seats come from the club before they go outside the club.”
The 4 ½-month Board of Directors Program he founded teaches C-level executives and two levels below the technical and governance aspects of sitting on a publicly traded or private board, as well as the nuances.
The tuition-free program has trained about 140 fellows so far; 17 have gone on to get board seats. More recently, it has been working to accelerate results by asking companies to add an advisory slot to their boards for program fellows, who would fill the skill sets deficit that the boards currently have while getting board experience and building a board brand.
In today’s economy, the value of a company is intangible assets—brand reputation, intellectual property, and innovation—which are more valuable than physical assets. Boards that cultivate diverse perspectives, industry expertise, and strategic foresight are better equipped to anticipate risks, seize opportunities, and drive sustainable growth.
“The value of a company today is based around what sits on technology,” Giles said. “Therefore, for the company to thrive and live in perpetuity, you have to have those individuals who understand the transformational impact of technology on the business. That’s why technology professionals are starting to be in demand.”
The average age of board members has dropped, sometimes significantly. If, when Giles was first invited to join a board, he was a youthful anomaly, today boards are increasingly bringing on younger members – some in their twenties — because they’re digital natives, and the customer base of the company, he said.
Historically, boards were made up of CEOs, CFOs and COOs. But that paradigm is also changing, he said.
“In today’s business landscape, 80 % of the value of a S&P 500 company doesn’t sit on its
balance sheet its intangible assets such as (Brand, patents, IP, workforce etc.) Today, there is so much risk to a company because of technology and change,” he said. “So having individuals who understand the impact of technology, the value of technology, and how technology is a driver of earnings per share and total shareholder returns – that is what is starting to fuel the shift.”
The other piece is the Security and Exchange Commission’s rules on cybersecurity, Giles said.
“In the past, boards put technology skills in the specialized skill set bucket and didn’t view technology skill directors as culturally relevant, but that has changed,” he said. “They see how AI’s transformative potential and cyber risk will put the company’s reputation on steroids. They understand that the board composition has to both change and expand to implement this degree of fiduciary oversight.”
Board opportunities with private companies are more plentiful because the number of public companies is limited, he said. “But I would not focus on a private board versus a public one. I would go for both of them,” he said.
When looking at a possible board seat, CISOs shouldn’t rush into a commitment, Giles said.
“Sometimes because they’re so anxious to get on a board, candidates make the mistake of taking the first one to come along. That’s a bad idea. You’re talking about a 10-year commitment on average, so you have to be sure that you want to be in a relationship with those individuals sitting around the table for 10 years.”
When interviewing for a board seat, candidates ought to meet individually with each board member to get a sense as to whether the placement would be a good fit, he advised.
Board members will need to devote about 400 hours a year to their board duties, and crises that erupt can take them away from their day jobs, he said. Candidates must therefore get their employer’s permission to accept a board offer, Giles said.
To deal with competing claims on their attention, CISOs need to do tabletop exercises at their enterprises, be aware of developments in their own industry and have processes and oversight in place, he added.
To shield themselves from possible liability suits, prospective board members should get a copy of the company’s D&O insurance policy and consult with their personal lawyers to determine what sort of protections they would have, Giles said.
“Most people do not do that. They have no idea what exposure they may have from a personal perspective,” he said.
A top question boards will ask prospective candidates is how would your skills add value to our board of directors, Giles said. Another is, when was the last time you had to stand alone?
“You might have an issue where all the other board members say yes, and you say no, because the board’s fiduciary duty is individual, not collective,” he said.
A top question a candidate should ask the board is what does it see as emerging trends in the relevant industry or sector that technology can address, he said. Candidates should also ask whether the board has a speak-up culture, he added.
“Do your board members have direct access to major shareholders? Are they allowed to sit in on operational meetings in a listening capacity? Do you encourage board members to visit customers and suppliers? If the answer to these questions is no, it signals a deeper issue—an insecure CEO who treats the board as a rubber-stamping body rather than a true governance partner.
“A healthy board fosters open dialogue and strategic engagement,” Giles said. “If management dominates 70% of the conversation in board meetings, you’re not in a discussion – you’re attending a board governance concert. And that’s a key indicator of ineffective governance.”