Deidre Diamond, Founder & CEO, CyberSN and Founder, Secure Diversity

Deidre Diamond, founder and CEO of CyberSN, transformed the cybersecurity job search and hiring process by launching a deepjobs matching platform and standardizing all cybersecurity job functions into a common taxonomy of 45 roles. Deidre also founded and the Day of Shecurity conference to help promote diversity in cybersecurity. Deidre has 29+ years of experience in technology and staffing, leading teams at Rapid7 and Motion Recruitment. She received the Top 25 Women in Cybersecurity award by Cyber Defense Magazine and is a sought-after speaker who inspires individuals to join the cybersecurity industry while driving change in the industry.

Recently, in an exclusive interview with Digital First Magazine, Ms. Diamond shared her insights on the major trends and changes rising in the cybersecurity landscape, the inspiration behind establishing CyberSN, the mission and vision of Secure Diversity, pearls of wisdom, and much more. The following excerpts are taken from the interview.

What major trends and changes do you see rising in the cybersecurity landscape?

We are currently witnessing significant volatility, particularly in cybersecurity roles that are not compliance funded, within the U.S. job market. As the economic climate is volatile in itself, it seems that employers are prioritizing compliance and not investing as much in security practices. We see this in the job posting data that is posted on the CyberSN platform. At any given time, there are around 190,000 active jobs posted at CyberSN and this data shows compliance related roles staying steady and all other roles drastically dropping in postings. Additionally, we have observed many organizations putting cybersecurity open jobs on hold. This is giving further stress to the market that was already overworked. So, we are now seeing professionals reaching out looking for job matching support to get into an organization that is thinking more strategically about cybersecurity talent.

What are your thoughts on diversity and inclusion? How important is it to have authentic conversations with leaders, professionals, and changemakers to create more acceptance across the globe?

Diversity and inclusion are an absolute must. Our attackers are diverse. If we are to defend ourselves, we must also be diverse. By embracing diversity, we gain a deeper understanding of how others think, feel, and perceive the world, even if we don’t share the same life experiences. Therefore, diversity within the cybersecurity job landscape is not just important, it is imperative. Women constitute 51% of the marketplace and if we fail to include women in the cybersecurity workforce, we will be limiting our ability to effectively defend ourselves against adversaries.

Deidre, can you tell us about your professional background and areas of interest?

My professional journey began in the early 90s, shortly after graduating from college with a degree in sociology and criminal justice. It was during this time that I came across an advertisement in the paper placed by two ambitious entrepreneurs seeking someone who could think on their feet. Intrigued, I joined them and underwent training to become a technical recruiter and a leader capable of growing and scaling organizations. I was taken seriously and provided with the necessary support and guidance to succeed. With this newfound opportunity, I dedicated 13 years of my career to building Motion Recruitment, transforming it into a thriving $89 million enterprise before leaving. This experience propelled me into the realm of security software sales, where I was honored to become the first Vice President of Sales at Rapid 7, RPD. Through this role, I developed a deeper connection to my criminal justice background and developed a profound passion for the cybersecurity profession. Afterward, I embraced the role of CEO, working alongside the same founders and then later decided to found my own company, CyberSN. Two years later, I founded a non-profit organization, Secure My interests are building organizations that solve important problems while fostering cohesive teams of individuals who genuinely enjoy working together. Beyond my professional pursuits, I find joy in a variety of activities, including walking, practicing yoga, socializing, and being in nature.

What was the inspiration behind establishing CyberSN. What sets it apart from other market competitors?

The time had come for me to establish my own company. The gentlemen I worked for 21 years were retiring and I needed to keep going. Driven by my deep appreciation for working with cybersecurity professionals during my tenure at Rapid 7 and my passion for technical staffing I recognized an opportunity to merge these two passions and provide exceptional services to the cybersecurity community. Nine years ago, I founded CyberSN. Shortly after its inception, I realized that the job search landscape had undergone significant changes during the ten years I had been away. Matching professionals to suitable job opportunities now required an extensive investment of time, money and resources, making it a daunting, expensive task. I instantly started thinking about what’s needed to solve this job searching and match problem. A cybersecurity common language job taxonomy was the obvious need and that’s what we set out to do and did. First, we built an internal application using this taxonomy for job building and profile building. Three years later we launched our self-service matching platform for job posting and matching. We are now giving this gift of making job searching and matching at a much lower cost to employers and professionals. Today, we’re focused on scaling this offering so that everyone has access to easy job matching at a low cost.

Tell us about the mission and vision of Secure Diversity? Please share some of the initiatives taken by this non-profit organization to empower all genders and specifically women to find career opportunities in the cybersecurity industry.

Recognizing the rarity of my career path and the fact that I represented the less than 1% of women who had founded and self-funded their own software company, I felt a strong calling to make a difference. This realization led to the foundation of Secure Diversity, an organization dedicated to bringing women and underrepresented genders into the cybersecurity field, as well as supporting their career growth and development. Secure Diversity pursues its mission through various avenues. One notable initiative is the Day of Shecurity, a free conference that provides women the stage to learn from other women and allows for people to speak without having to sponsor an event. The most recent conference saw the participation of over 1000 women, both virtually and in-person. As a partner of the SANS Institute, Secure Diversity collaborates on multiple fronts. One significant collaboration involves the establishment of three cohorts focused on executive leadership in Governance, Risk, and Compliance (GRC), Cloud Security and Cybersecurity Operations. Through this partnership, we provide funding and support to women participating in these cohorts, enabling them to advance their careers and attain executive-level positions.

What are the top skills, both technical and soft skills, that are greatly needed as a cybersecurity professional in the current digital landscape?

From both a technical skills and soft skills standpoint, the cybersecurity job landscape encompasses 10 distinct categories, comprising a total of 45 functional roles. At, we provide a comprehensive mapping of these roles, allowing individuals to explore the necessary skills and qualifications associated with each position. When considering the soft skills perspective, it becomes evident that employers place great emphasis on professionals possessing high emotional intelligence. This encompasses the ability to genuinely care about how others think, feel, and perceive the world, fostering effective interactions and relationships. Additionally, creating a positive and productive work culture is crucial, promoting an environment where professionals enjoy collaborating and working together harmoniously. Problem-solving skills are highly valued within the cybersecurity field, as they enable professionals to tackle complex challenges and devise innovative solutions. Equally important is the ability to navigate and resolve conflicts effectively, ensuring that individuals can move forward rather than get stuck in unproductive disagreements.

In your academic or work career, were there any mentors who have helped you grow along the way? What’s the best piece of advice you have ever received?

Throughout my journey, from the very beginning until the point of establishing my own organization, I had the privilege of having mentors who remained by my side for many years. These mentors played a pivotal role in my personal and professional development, and I cannot overstate their significance in my journey. Interestingly, these mentors were individuals who happened to employ me, which underscores the importance I place on employer-provided mentorship. While external mentors can be valuable, I believe that internal mentors hold the greatest importance.

The best advice that I ever received is that nobody comes to work to fail. When I first started training others in recruiting, someone that worked for me didn’t follow my direction and I was not happy about it. It was at that point that my mentor, even decades ago and still relevant today, reminded me of this fundamental truth and to figure out why my communication had not been received effectively. From that day forward, I realized that it was my responsibility to ensure that my directives were not only delivered but also understood by everyone, not just those directly reporting to me. This realization has been invaluable to my career.

What has been your most career-defining moment that you are proud of?

The most pivotal moment in my career, one that I am immensely proud of, was when I earned the respect and support of highly successful entrepreneurs at a young age. It was not my age or gender that garnered their investment, but rather my daily dedication and accomplishments. I take great pride in having cultivated such relationships, as it has shaped my identity and set a standard for the rest of my professional life. From that moment forward, I made a firm commitment to myself and others. Nothing less than excellence was acceptable, both in the work I delivered and in the way I treated those around me. Age, gender, religion, or race were never going to serve as obstacles in my pursuit of success or hinder my interactions with others. This defining experience instilled in me a deep conviction to prioritize accomplishments, merit, and professionalism above all else. It propelled me to continuously strive for excellence and to foster an inclusive and supportive environment for everyone I worked with.

Where do you see yourself in the next 5 years?

I see myself surrounded by remarkable individuals, collaboratively tackling significant challenges, and consistently acknowledging the profound gratitude I hold for the foundation that has brought me to where I am today. That foundation was given to me by others, and I will forever feel lucky 5, 10, 15, 20+ years from now. Looking ahead, I remain committed to reciprocating the generosity I have received by uplifting others, sharing knowledge, and fostering an environment where individuals can thrive.

What advice would you give to cybersecurity professionals just starting out?

My advice to succeed in your career is to have a clear understanding of the specific role and career path you desire. By identifying your goals upfront, you can establish a stronger connection with hiring managers. Employers seek individuals who are genuinely passionate about the work they do. Therefore, take the time to explore the various roles and responsibilities within your field and determine which ones resonate with you the most. Another essential aspect is developing and owning your emotional intelligence skills. Mastering the art of win-win communication, active listening, looking at a problem with a 360-degree view, utilizing lean language, practicing empathy, and honing other emotional intelligence skills will empower you both in your professional and personal life. Building and nurturing relationships are essential to achieving success and finding fulfillment in your work. Remember to focus on relationships as much as you focus on other skills, and you will find more happiness at work.

Content Disclaimer

Related Articles