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Deidre Diamond

Founder and CEO, CyberSN and at CyberSN (

Staffing and Recruiting

Boston, MA, USA


As an early stage Vice President of Sales for software security provider Rapid7 (NYSE:RPD), I have combined my nearly 15 years of building technical staffing agencies with my cyber security software sales background to create Cyber Security Network ( with a mission to identify and deliver Cyber Security Professionals to employers quickly! I have had repeated success building winning cultures and I enjoy helping others do the same.

I am also the Founder of #brainbabe (, a not-for-profit thought leadership platform that aims to empower women to join the Cyber Security and Technology professions and to help all current Cyber Security professionals—both women and men—work powerfully together using its communication training. I hope to have many opportunities in 2016 to share my tools and ideas for success in the cyber security and technology communities.


Combining my 21 years of experience working in technology and staffing, my love for the cyber security community, and a genuine enthusiasm for people; I created Cyber Security Network (, a company transforming the way Cyber Security Professionals approach job searches. will remove the frustration from job-hunting, and aid in interpersonal connections and education.

Throughout my career I have built large-scale sales and operations teams that achieved high performances. Creating cultures based on an anything is possible attitude allows people to achieve above and beyond the usual. By establishing an open communication framework throughout an organization; I have created cultures of positive energy, career advancement and kindness, that enables teams to reach beyond peak performance and have fun at work.

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I am willing to travel

Up to 100 miles


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Best Story

I took a yearlong sabbatical starting in September of 2013. After 20 years of start-ups and operational 24/7 duties, it was time for me to take a break and spend a significant amount of time thinking about how I wanted to spend the second half of my career. I knew I was ready to start my own company, but where was I going to focus? How was I going to take my experience and turn it into wisdom that could help a significant number of people? I have always loved making a difference in people's lives, and I wanted to do much more. I needed no distractions of job ideas, job offers, or any conversations about jobs. I left my LinkedIn page unchanged, told very few people what I was doing, and for the first time since before college I took a break to think about the future.

What I realized during my non-operational time was this: Cyber Security Professionals don't have the time to conduct a well-rounded job search. Ultimately, they are left feeling frustrated, in part because their searches involve speaking to so many people who have no concept of what they truly do at work.

Having spent almost 15 years building technical staffing agencies around the country and training hundreds of technical recruiters from scratch for Motion Recruitment, four years with Cyber Security Software firm Rapid7 building the direct and channel sales force, and then three years running the large-scale website development software company Percussion Software, I was inspired to combine all three backgrounds and bring my network of Staffing Specialists to help change the way Cyber Security Professionals conduct job searches with

Origin Story

At only 26 years old, I was the Vice President of Sales for the national technical staffing agency Motion Recruitment and was in charge of leading the hiring, training and development of hundreds of technical recruiters from an entry-level college graduate hiring model. I then spent nearly 15 years building this organization up from 20 people to just over 500 people. Today, Motion is still growing and thriving.

From there, I took my technical staffing and leadership experience to Rapid7 (NYSE:RPD), arriving when it was a company of 18 people. As Rapid7’s first Vice President of Sales, I led the teams and strategy build-out of the National Sales team, Pre-sales team, Professional Services team, Customer Success team and their Internal Recruiting Team. My leadership resulted in Rapid7’s new sales revenue increasing from $800,000 to $20M in four years—consequently creating $45M in new revenue generation (excluding renewals.) I then became the CEO of Percussion Software, where I led the release of their new content marketing software and learned the ins and outs of digital marketing, content marketing and web development.

Combining all three of these experiences, I am now the Founder and CEO of a national cyber security staffing company—comprised of highly trained cyber security staffing specialists and web technology—Cyber Security Network (CyberSN), which is changing the game of cyber security staffing. The skills that I now have are transferable and I am committed to seeing more people, particularly women, possess them. I strive to share and create a new way of hiring and retaining women in cyber security through both CyberSN and my not-for-profit thought leadership platform #brainbabe (

Example talks

"Soft Skill Matter"

The numbers don't lie - cybersecurity is losing people faster than they are joining the industry. In this talk, Deidre explores why this is happening and what we can do to turn this trend around.

"W.A.R. Words Are Risk"

Words can start and end wars and they can also build workplace cultures up, or tear them down. In this talk, Deidre shares simple changes that leaders and teams can make to improve communication and reduce breakdown.

The "Best Ways" To Hire, Attract, and Retain Talent

The cybersecurity industry has a massive retention problem. In this talk, Deidre Diamond shares what it takes to create cultures of high-performance with retention.

All Leaders Can Be Cyber Security Savvy

The importance of cyber security savvy leaders!

A Unique Approach: Job Information for Cyber Security Professionals

How to interview for the job you want, how to create your resume, how to manage things in a candidate driven market, and how to know what folks look for in the screening process.

Talking Total Compensation

How to make sure that you are discussing the "big picture" when you negotiate salary.

What Kind of Agreements Do You Make?

Making agreements in the workplace and keeping them. How can we be better communicators and where can we improve to drive efficiency?

The State of Cyber Security in New England

What's going on with the job market for cyber security professionals in New England? Deidre discusses trends, gives real-world examples, and gives tips for hiring quickly and more efficiently.