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Rob Cheyne is a seasoned security expert with extensive experience in penetration testing, network security, and application security. He has held various leadership positions, including Founder and CEO of Big Brain Security, and has worked with prominent companies such as Symantec and @stake. With a strong educational background from Harvard Law School, Rob brings a unique blend of technical expertise and industry knowledge to his work.

Experience

  • Big Brain Security
    • Greater Boston Area
    • Founder, Chief Executive Officer
      • Feb 2014 - Present
      • Greater Boston Area

      At Big Brain Security, we are Infosec industry veterans who want to actually fix the problems we see, not simply perpetuate the status quo. We are passionate about developing and delivering smart security solutions that are both high-impact and high-value. We want to make the world a better, more secure place, and we’re going to have a lot of fun doing so. Our initial offerings seek to blend the best of InfoSec consulting with the best of in-person training. We combine deep consulting experience with deep training experience to create something we believe is truly unique in the InfoSec market.Seminars:- Security Therapy Seminar- Security Awareness Seminar- Application Security for ManagersWorkshops:- Architecture Assessment Workshop- Real Risk Assessment Workshop- Incident preparedness workshop- Information Security Train-the-TrainerCheck out our website to learn how we can transform the way your company thinks about information security.

    • Executive Director
      • Jun 2013 - Present

      SOURCE Conference: A Global Security, Business, and Technology Forum www.sourceconference.comNext session: April 8-10, BostonSOURCE Conference brings security professionals and practitioners together in an intimate and personal environment to discuss the security industry’s most important issues, technologies, and business trends. Responsibilities include:- Strategic planning and business development for the SOURCE Conference. - Work with the advisory board and volunteer committee to manage all aspects of the conference.

    • Advisory Board
      • Nov 2007 - Present

      Assist in strategic planning, event planning, speaker/talk selection, and other various conference duties that need to get done each year.Participated as an advisor since day one, and helped build the Source:Boston conference into a 300+ attendee annual event.Participated in the development and rollout of Source:Seattle.

    • Chairman of the Board
      • Dec 2012 - Jul 2014

      After leaving my full-time position as CEO of Safelight, I retained my role of Chairman of the Board. In this capacity, I provide feedback and guidance to Safelight on an as-needed basis, and participate in quarterly board meetings.

    • Founder, Chief Executive Officer
      • Jun 2007 - Dec 2012

      Safelight is an information security education company that provides role-based application security and information security awareness/privacy training. Training is delivered in both instructor-led and e-learning formats.Accomplishments include: - Along with my business partners, created a world-class team and processes for developing relevant, best-in-class security education - Successfully bootstrapped a multi-million dollar software product company during an extremely difficult economic climate, while taking on minimal private investment. - Built the company from a small initial investment into a market-leading business which regularly out-competes much larger, better funded competitors. - Delivered training solutions to over 200 customers in government, finance, health care, big retail, utilities, insurance and entertainment industries. - Led Safelight’s global instructor led training practice, delivering training in 9 countries to over 20,000 students. - Pioneered new techniques for developing and conducting in-person instructor led training using accelerated learning. - Designed and developed an innovative application security education curriculum that was rolled out to numerous Fortune 500 and other global, market-leading companies - Participated in the design and roll-out of Safelight’s corporate trade show presence, including multiple years as an RSA Conference silver sponsor.

  • Pwnie Express
    • Greater Boston Area
    • Interim CEO, Interim Director of Engineering
      • Apr 2013 - Nov 2013
      • Greater Boston Area

      - Helped lay the foundation for the Pwnie Express team to receive $5.1M in Series A venture capital- Conducted a custom-built Startup Bootcamp training session for the entire company- Assisted in recruiting efforts and establishing company policies- Provided leadership & direction for the engineering team- Created an engineering plan that included all product lines- Assisted with Pwnie’s trade show presence for Black Hat and Defcon 2013

    • Principal Security Instructor
      • Oct 2004 - May 2007

      (acquired @stake). Taught application security, network security and security awareness classes for managers, architects and developers at Fortune 500 companies, primarily large financial institutions

    • Managing Security Architect
      • Jan 2000 - Oct 2004

      - Founding employee of @stake- Helped design, develop and roll out assessment methodologies that are still in use by the information security industry today- Conducted secure architecture, design, code reviews, and application penetration testing for Fortune 500 companies- Developed LC4, an award-winning password auditing tool- Worked on SmartRisk Analyzer, a tool for locating security vulnerabilities in applications.- Conducted enterprise security training courses on application security, infrastructure security, and cyber attacks

    • Principal Security Consultant
      • Aug 1998 - Dec 1999

      Information security consulting:- Secure architecture & design reviews- Secure application implementation- Public Key Infrastructure (PKI) Deployment

    • Senior Consultant
      • May 1996 - Aug 1998

      - Founding member of professional services organization- Architecture design & review for client e-commerce projects- Customized e-commerce products to meet customer requirements (Transact, OM-Axcess)

    • Staff Consultant
      • Jun 1994 - Dec 1997

      - Systems integration consulting for fortune 500 companies.- Worked on the integration testing team for a major pharmaceutical client's system roll-out.- Helped establish a professional services organization for a pioneering e-Commerce product vendor.

    • Senior Software Engineer
      • Sep 1989 - May 1994

      - Designed, built, and tested MediaPhile video editing software applications on the Commodore Amiga platform. The applications were coded primarily in C.- Handled 2nd tier technical support for the entire product line.- Hand-assembled video editing hardware controllers

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Industry Focus. “Computer and Network Security”

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