Michael Leland is Field CTO at Island, bringing over 30 years of data networking, operations, and cybersecurity domain expertise.
Michael formerly served as Head of Technical Marketing and Chief Cybersecurity Evangelist at SentinelOne, where he was responsible for messaging and strategic development of their XDR product roadmap as well as the identity security portfolio.
Prior to SentinelOne, he held the title of Chief Technical Strategist for McAfee. Michael was the co-founder and CTO of NitroSecurity, later acquired by McAfee, where he was responsible for developing and implementing their overall SIEM technology vision and roadmap. He has also held senior technical management positions at Cabletron and Avaya.
Michael is featured in this ongoing leadership series developed by Cybersecurity Collaborative and SC Media, examining how experienced security leaders think about their role and its evolving challenges.
To learn more about the Cybersecurity Collaborative — a membership community where cybersecurity leaders collaborate in a trusted, peer-driven environment — click
here.
Below, Michael shares his experiences and perspective.
What does your company do?
Island is a reimagining of enterprise work. A single space, where everything organizations need to work safely and productively is built in. From the desktop to the browser to the network, Island provides comprehensive data protection, intelligent application access, and governed AI adoption.
Island delivers an enterprise control plane for AI agents and enables use cases that deliver enhanced data protection and reduce costs and complexity while improving end-user experience and workforce productivity.
What keeps you up at night?
Rapid organizational growth can quickly erode business culture. Sometimes the leadership team that got you to $1B ARR may not be the right ones to get you to $10B or $100B. The go-to-market strategy of a startup may not scale to accommodate the needs of a larger, more mature organization. I fear that the culture of a start-up may not transcend rapid growth.
What is the best leadership advice you have ever received and by whom?
The single best piece of leadership advice I rely on comes from Retired Navy SEAL Commander Jocko Willink: "Extreme Ownership: Leadership is not about deflecting blame; it is about owning every outcome, good or bad."
When a team fails, an executive's immediate instinct might be to point to resource constraints, poor communication, or individual mistakes. Extreme Ownership flips that dynamic entirely. If a team member makes a mistake, the leader failed to train them. If a project misses a deadline, the leader failed to manage resources or clarify priorities.
By accepting 100% responsibility for every operational flaw, you eliminate finger-pointing, build immense trust with your team, and empower yourself to solve problems directly rather than waiting for others to change.
How do you earn and maintain trust with your team?
Trust is earned and lost by how we follow through on our commitments to team members. Consistent, respectful communication to my team helps build trust and confidence that I'll have their back.
I don't make promises I can't keep, and I don't leave communications unanswered for any length of time. Days matter, people matter, and timely, honest, candid responses remind my team that we're all in this together.
When pressure is highest, what principle guides your decision-making more than anything else?
Act decisively, but from an informed position. Difficult decisions arise from difficult questions. Acting rashly often makes the situation worse, but not acting at all will most definitely fuel the conflict.
We're all expected to wear multiple hats. Bringing the right resources to bear, even if you're not a first-party contributor, is the most effective way to collaborate on the proper response.
What do high-potential leaders consistently misunderstand about what it takes to move to the next level?
High-potential leaders often hit a ceiling because they assume the skills that made them star individual performers will automatically propel them to executive ranks.
Moving to the next level isn't a step up in degree. It's a pivot in identity from doing the work to amplifying systems, people, and strategy.
What moment in your career most clearly marked your "ascent" into leadership, and what was the road that led you there?
I have always been a "builder," having led the technical initiatives at multiple start-ups over my career.
Starting from the network-engineering lens gave me a solid understanding of the underlying mechanics of data transport. Transitioning to network security — and building a team of developers to address risk and governance — provided the next stepping-stone of my career. As Chief Technology Officer, I was required to bridge my technical skills with executive outcomes.
How do you work to create a positive corporate culture, and how do you handle morale issues when they come along?
Creating a positive culture requires establishing psychological safety through blameless post-mortems, institutionalizing recognition, and respecting work-life boundaries to prevent burnout.
When morale drops, act swiftly by listening without defensiveness to validate team concerns. Identify whether issues stem from toxic dynamics, resource constraints, or poor communication.
Rebuild trust by maintaining absolute transparency about what can change immediately, then execute quick, visible wins while committing to long-term systemic fixes.
What leader do you most admire?
Mike Fey, CEO of Island, and Jen Easterly, former Director of the Cybersecurity and Infrastructure Security Agency (CISA).
Leading is hard. How do you manage the stress of it?
Managing work and personal life balance is always challenging, especially in startup environments. Having a social relationship with your team and others across the organization helps bridge that gap.
But hard work must be rewarded with personal time to recover. Don't skip vacations and find time to truly disconnect from work whenever possible. Put Slack on DND. Don't check work emails. Make sure you have adequate coverage while away so that you can truly relax.
Is there a particular leadership book you would recommend?
Slightly off the leadership topic, but still incredibly relevant: The Innovator's Dilemma by Clayton Christensen is a famous business book published in 1997 that explains why great companies fail when new technologies arise.
It describes why the first product to achieve a capability most often will not be the one that achieves the greatest success. It talks about rapid iteration and measuring change over time. It reminds me why both velocity and excellence must run parallel and not in series. It redefines the concept of MVP.
What excites you about leading a team?
I enjoy building and nurturing a team of highly professional technical leaders. I enjoy mentoring those both inside and outside my orbit to build a highly effective engine that delivers exceptional outcomes to our customers and our employees alike.
I like to see those under me see the recognition they deserve across the organization so we can share the successes together. We also must share the failures to ensure everyone understands the risks, the pitfalls, the errors made that can impact the success of the organization.
What has surprised you the most about being a leader as your scope and visibility have increased?
Managing a team of developers is very different from managing customer-facing technologists. Ensuring that engineers (coders) stay maniacally focused on meaningful customer outcomes, while delivering a set of capabilities that sales engineers can quickly deploy and show business impact, is a difficult task.
As a leader, understanding the fiscal impact of every decision matters. Feature prioritization, impact to revenue attainment, minimizing churn, and delivering a superior customer experience —each has a measurable impact on profitability. People and culture can be the deciding factor of whether a company grows from a startup to a highly successful company.
What role do communities like CRA's CyberRisk Collaborative play in your success?
My personal and professional networks have grown immeasurably over the years from participation in communities like the CRC.
I have met peers from whom I have learned critical perspectives about my business, my leadership skills (and gaps), and my goals. I have both fed talent into and recruited talent from these communities. I get to socialize ideas and opportunities within a safe, respectful group of like-minded individuals.
What soft skills did you need as you moved up within the organization and managed teams?
To scale into executive cybersecurity leadership, your technical expertise must evolve into strategic organizational influence.
Success relies on translating complex cyber threats into core business metrics like revenue, financial exposure, and operational resilience to gain buy-in from non-technical stakeholders. Executive diplomacy and consensus-building take priority over relying on fear, uncertainty, and doubt (FUD) when negotiating with the CEO, CFO, and board.
At the team level, effective leadership means adopting a servant mindset — delegating daily execution to empower your staff, cultivating psychological safety to prevent burnout, and keeping your focus on long-term strategy.
What was the hardest decision you had to make as a leader?
Identifying a no-win situation that was outside my sphere of influence and deciding to make an early exit.
I had grown my first startup to a point where new executive leadership was required. Our investors selected a new CEO, CFO, and COO from a much larger organization. This C-suite tried to implement rigid processes that were counter to the culture and the environment I had built. Customer churn and employee dissatisfaction began to occur.
While this was my "baby" that I had struggled to make successful, I realized that I would be unable to steer the ship under this new management structure and decided to walk away. That company folded within a year, weighed down by cost and complexity introduced by the changes.