An Exclusive Rendezvous with Simon Chassar | #hacking | #cybersecurity | #infosec | #comptia | #pentest | #ransomware

A distinguished executive in enterprise technology, cybersecurity, and services, Simon Chassar has an impressive track record spanning over two decades. Boasting international experience, Simon has been at the forefront of leading sales and business operations in the SaaS, software, hardware, and IT sectors.

Simon recently completed a successful three-year tenure as the Former Chief Revenue Officer of Claroty, a testament to his prowess in navigating the complex realms of global cybersecurity sales, technical pre-sales, operations, commercial, field marketing, tech alliances, and channels functions. His role at Claroty was pivotal in safeguarding the industrial economy and healthcare systems from cyber threats, underscoring his commitment to securing critical infrastructure in an increasingly digitalized world.

Prior to his impactful stint at Claroty, Simon held the position of Executive Vice President and Chief Revenue Officer of Cybersecurity at NTT, further solidifying his leadership in the cybersecurity domain. Now, as an Advisor for Claroty and gearing up for new roles in 2024, Simon is on a mission to guide cybersecurity technology providers and services organizations in overcoming the challenges of scaling to $100M+ in revenue. His expertise will also be instrumental in preparing these entities for public company readiness and navigating strategic shifts in the ever-evolving landscape.

Simon’s vision extends beyond revenue goals; he is deeply committed to helping organizations meet new cybersecurity regulations and ensuring business continuity in the era of Digital Transformation Acceleration and Industry 5.0. With a strategic mindset and a wealth of experience, Simon is set to play a vital role in shaping the future of cybersecurity and fortifying businesses against emerging threats.

Professional Journey

Simon reflects on three pivotal moments in his career that significantly shaped his professional journey. The first was his entry into the world of networking with Cisco Systems in 1999. Tasked with analyzing service provider product sales and reorganizing the go-to-market (GTM) strategy, Simon gained insights into using data strategically for growth. He also learned from some of the best sales leaders during the hyper-growth phase of networking, unified communications, and network security operations in the early 2000s.

The second transformative moment occurred in May 2007 when Simon joined VMware before it became a public company. At VMware, he created the Enterprise License Sales team, focusing on client transformation journeys, particularly the shift from physical servers to virtualization. By projecting return on investment (ROI) and cost savings from workload consolidation, hardware and storage efficiency, Simon and his team successfully sold multiyear Enterprise License Agreement (ELA) subscription contracts, contributing to over $300 million in annual revenue.

The third significant milestone took place at NTT, where Simon delved into cybersecurity technology controls and services. He recognized the challenge of a growing volume of false positive alerts due to the increasing complexity and innovation in cyber toolsets. This led to the concept of “Secure by Design,” emphasizing the need for building cybersecurity into digital transformation initiatives at the ground level. Simon highlighted the importance of accurate contextualized threat monitoring and saw the new frontier in digital transformation with the increasing connectivity of Industry 4.0. Attracted to Claroty’s mission of protecting society, Simon joined the team as Chief Revenue Officer (CRO) in 2020.

Key Challenges in the Evolving Cybersecurity Landscape

Simon identifies several key challenges in the cybersecurity landscape. First and foremost is the escalating threat posed by cyber-attacks originating from nation-states and increasingly sophisticated criminal actors. This necessitates organizations to swiftly adopt new technology solutions to address critical issues such as skills shortages and the growing complexity of cyber technology management. The use of Artificial Intelligence becomes crucial in developing advanced, machine-driven defensive strategies to counteract these evolving threats.

Additionally, the impact of techno-nationalism and geo-political uncertainties adds another layer of complexity. Organizations are under pressure to act quickly in adopting new technologies to navigate this uncertain landscape effectively. Cloud and AI for Cyber emerge as focal points in the strategic response to these challenges.

The landscape is marked by the dual challenges of regulatory compliance and technology debt. Organizations must navigate the complexities of meeting new regulatory requirements while simultaneously addressing the accumulated technology debt from the Covid Era. This is particularly challenging given the budget pressures resulting from market headwinds.

Leadership Principles

As a leader in the cybersecurity domain, Simon adheres to key leadership principles: putting people first, emphasizing integrity, and maintaining a customer-centric approach. Additionally, he follows the CIA principle:

  • C (Control): Evaluate whether you have the resources and means to control the situation, objective, or goal. Focus on applying yourself and utilizing available resources effectively.
  • I (Influence): Assess whether direct control is not possible but influence is achievable. Take strategic actions to influence the outcome positively.
  • A (Accept): When neither control nor influence is feasible, accept the situation. Avoid unnecessary stress and anxiety, understanding that certain aspects are beyond control.

Simon emphasizes the importance of radiating positive energy and behavior to influence the team positively, creating a momentum multiplier that starts at the leadership level.

Framework for Hypergrowth

Simon introduced the concept of the three Ps in the hypergrowth startup lifecycle:


  • Objective: Demonstrate a solution to a new problem or existing challenge, making the innovation noticeable.
  • Focus: Market penetration without requiring extensive collaboration.
  • Result: Establish a presence by showcasing a viable solution.


  • Objective: Build a strong foundation with the right team, product, packaging, messaging, routes to market, market focus, and results.
  • Focus: Collaboration across cyber services and partner ecosystems to protect the position as a solution provider.
  • Result: Strengthen survival and establish the startup as a reliable solution provider.


  • Objective: Encourage collaboration and alliances across the industry to solve problems collectively.
  • Focus: Extensive collaboration and alliances, including co-opetition, to address industry-wide challenges.
  • Result: Unite the industry against common adversaries, fostering the sharing of intelligence and IP for the greater good.

The three P’s represent distinct phases in the startup journey, emphasizing different aspects of growth and collaboration.

Team Building and Career Guidance

Simon prefers to hire individuals whom he trusts, but he also seeks out those who exhibit a stronger inclination towards intrinsic motivators on a psychological level. While many individuals still aspire for material gains such as a better house, car, or life for their families, Simon values those who find fulfillment and excitement in being part of a journey, a team, or a mission.

He believes that this mindset contributes to the scalability of the organization during hypergrowth, fostering a collaborative environment where everyone relies on each other, adapts well to change, and cultivates a contagious motivational spirit that generates energy and results for the team.

In guiding one’s career path, Simon recommends setting realistic goals for career progression. He emphasizes the importance of acting with integrity and treating others with respect, especially in an industry that thrives on trust and delivering results. Simon advises against compromising one’s integrity and stresses the significance of avoiding disrespectful behavior, given the relatively small network of relationships in the industry.

Championing Inclusivity in the Cybersecurity Sector

During Simon’s tenure at Claroty, the company embraced a progressive stance on gender diversity, exemplified by having five female members on the executive team. Claroty advocated for an inclusive approach to hiring and promotion, irrespective of individuals’ backgrounds, race, or identity. Simon, personally invested in this cause as the father of two girls, aspires for the industry to go even further.

He envisions a cybersecurity sector that not only supports inclusivity within the workplace but also actively promotes cybersecurity opportunities for women in schools and colleges worldwide. Simon is committed to contributing to the advancement of gender diversity in the field, fostering a more equitable and inclusive future for the cybersecurity industry.

Innovating Safely in Cybersecurity

Simon emphasizes the importance of adhering to frameworks like NIST, ISO27001, SOC2 or CES, or any other relevant ones in the industry. He believes that as long as innovation aligns with the goal of enhancing cyber posture, reducing risk, and meeting governance requirements, organizations should actively seek out innovative technologies.

Simon advocates for a proactive approach in adopting these technologies to accelerate a secure digital transformation. For him, the key is to embrace innovations that contribute to the overall safety and efficiency of the transformation process, enabling organizations to evolve rapidly in the digital landscape.

Approach to Staying Informed

For Simon, staying informed about emerging trends involves monitoring threat intelligence reports, tracking innovations from leading cybersecurity technology companies, and closely following Venture Capitalists and Private Equity firms investing in technologies addressing current or future problems.

Connecting insights from entrepreneurs and technologists with changes in the digital landscape, macroeconomic shifts, or geo-political changes helps him stay aware and learn more about emerging challenges.

This approach supports organizations in achieving hypergrowth by addressing client needs and delivering outcomes.

In his Advisor role at Claroty, with a large client base and a team of skilled cybersecurity engineers in R&D, they are well-positioned to respond to emerging threats in critical national infrastructure and operational technology.


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