Veteran Owned with customer service at the of everything we do.

Operating out of Illinois since 2008 RedLegg is a master provider of information security services. RedLegg is a boutique, nimble, old-fashioned customer service company that enjoys the technology battlefield. Knee-deep in the community, RedLegg enjoys crafting solutions designed to find, document, monitor, & eliminate the risks & vulnerabilities unique to your business. RedLegg’s corporate office is located in Geneva, IL. RedLegg 24x7 Support Engineers are located all over the United States.

We are Soldiers. Here to support, grow,and protect.

ARMEE Methodology

RedLegg’s approach to consultancy is based on a solid risk management foundation. We’ve branded our own methodology, ARMEE, in order to apply a holistic, lifecycle approach to risk management.

A thoughtful approach
to customer service

Not only do we carefully design the right risk management solutions for every client, we also take the time to thoroughly explain the ins & outs of these solutions to our stakeholders. We like to answer your questions before you’ve even asked them. In other words, we’re always available, no matter the request, to attend to our client’s needs.

Geek out with us!

We live, breathe, & socialize around our industry. That’s why we love hosting community events for our team members & clients alike. In addition to executive retreats & educational seminars, we also organize golf outings, happy hours, a weekly trivia quiz that keeps everyone on their toes, and more!


Lynn Weddle Lynn Weddle
Laura Hees Laura Hees
Stewart Williams Stewart Williams
Andrey Zelenskiy Andrey Zelenskiy
Michael Smith Michael Smith
Phil Grimes Phil Grimes
Kevin O’Toole Kevin O’Toole

Lynn Weddle

Founder, Co-Partner

Lynn Weddle founded RedLegg in 2008 & is currently a co-partner. With a career in the information data protection industry spanning over 20 years, Lynn determined the strategic direction of the company & crafted RedLegg into a successful & honorable corporation. He received a degree in Finance from Southern Illinois University & served in the Illinois National Guard for 15 years. Twitter @1RedLegg

Laura Hees


Laura has spent more than a decade developing revenue growth opportunities and sales direction for RedLegg. Laura’s customer-centric attitude and focus on the infrastructure and security industry has allowed her to develop new programs, expand on current ones and consistently exceed annual revenue targets for RedLegg. Laura holds a Kinesiology degree from the University of Michigan and is giving the Iron Man Events a try. Twitter @RedLegg

Stewart Williams

Director of Operations

Stewart Williams comes to RedLegg with over 20 years in Managed Security Services. Stewart is an experienced team & process builder with experience building both US & Global operational & deployment teams. With a focus on efficient process creation & adaptive troubleshooting, Stewart sets the direction for RedLegg’s Managed Security Services and Operations.

Andrey Zelenskiy

Director of Advisory Services

Andrey holds a Masters in Electrical Engineering and has more than 15 years of InfoSec Management & Consulting experience working with Fortune 100 companies in Financial, Healthcare, Pharmaceutical, Legal and Packaged Consumer Goods Industries. Andrey has a wide range of intelligent and InfoSec talent and knowledge making him to be an outstanding vCISO and vDPO as well as a strong leader of the delivery services team. Andrey is professional and efficient. He also enjoys cooking!

Michael Smith

Sr. Manager of Technology Services

Michael Smith is a long-time veteran of creating and maintaining solutions for complex security and information technology problems across multiple verticals. As a Sr. Manager of Technology Services for RedLegg, Michael has a diverse IT background, although his true passion remains cybersecurity. He has provided expertise on security subjects such as strategic planning, BYOD, governance, policy development, vulnerability management and assessment testing.

Michael is a strong proponent of continued growth and education. He is currently a Doctoral candidate at Capital Technical University, researching gaming in security awareness education. He holds a Master’s in Information Assurance and maintains several certificates including his CISSP and OSP. Twitter @drbearsec

Phil Grimes

Manager of TradeCraft Labs

Phil is well versed in providing logistics, security assessments and penetration services for over a decade. A passion for the digital world lead Phil to the professional security industry in 2009 as a vulnerability researcher; he eventually became a proficient penetration tester and accomplished exploit developer. Phil’s experience in application security, physical & digital penetration testing, mobile security and social engineering has proven valuable in assessments for high-profile customers both domestically and globally. A regular speaker and presenter, Phil has brought many topics to life for OWASP & ISSA, several security industry related conferences and various other speaking appearances to a wide range of audiences.

Kevin O’Toole

Manager of MSS Operations

Kevin specializes in the oversights of all MSS staff and client relations. He is a master of developing workflow processes to increase the quality of analytics, decisions and action items. Kevin coordinates work assignments based on skill level and availability and executing internal audits to ensure service milestones are met. In addition, Kevin oversees day to day processes such as work orders being closed appropriately and ticket entry review and customer service. Finally Kevin is a runner when his back does not hurt and can run fast carrying a pumpkin.

Common Questions.

What does RedLegg mean?
Well, nothing, it is the company’s name. But “RedLeg” (one g) is slang for field artillery personnel. The term goes back to the American Civil War & referred to the 2” red stripe that was sew on each pant leg of their uniforms. Artillery soldiers were considered to be the elite back then. Most likely because the number of casualties that they inflicted on the battlefield. Artillery killed the lion share of the enemy (around 75%) so they were known as the king of battle. While Lynn was at Fort Sill for his artillery training, he was shouting instructions to fellow redleg’s. He then started to use redleg & his favorite football number as his password for everything. When thinking of the company name, he decided against his name initials but why not a name from a password that would not leave his head? He has since then changed his password & thus the birth of redlegg.
Do you sell products, services or both?
Why should I do business with you? There are other and so much BIGGER security partners!
We truly care & want to make a relationship with you & your company. We are not interested in a quick sale. We could talk & write all day about this. Meet with us, request a quote from us & you will see. We are different.
Why do you guys think you are so smart?
We are! Test our knowledge. Work with us & you will see. Our methodology is better. Our reports are better. We take things seriously. We do things the smarter way.
Are you a mom & pop shop?
Yes there are some marriages, family ties & moms & dads. Maybe we could try a no dating policy? Nah.
What do you NOT do?
We are not an auditor. We do provide GAP assessments but we are not an auditor.
You have a SOC (Security Operations Center)? Cool, tell me more.

Managed Security Services is a big growing part of our business. Client Infrastructure is **Not** hosted in our datacenter. It is hosted on your site and RedLegg simply VPN’s as an employee to review log & threat sources. Click here to learn more.

Who is your target customer?
Including but not limited to legal, insurance, financial, manufacturing, healthcare & companies between 250 & 100,000 users.
Do you have in-house engineers? How many? How big is RedLegg?

Yes! We have in house security engineers. Of course! We are less than 50 people. Small but extremely efficient.

Do you only serve the Chicagoland area?
Good gosh no! Our corporate office is located in IL. We currently support customers in 50 states & multiple different countries.
What do you guys do for the world? Is it just about you & profit & more money? Gosh, you are just like everyone else.
Yes while we are a for profit company, we do believe in giving back. We proudly support multiple different charities and children’s organizations throughout Illinois.