Keeping workplace technology up and running is vital to any organization’s success. While this task seems feasible, it’s growing harder and harder each year as cybercriminals expand their reach.  It’s not enough to simply protect workplace technology with software and security protocols. It’s also critical for your organization to test the overall effectiveness of these protocols on a regular basis. That’s where penetration testing can help.

Essentially, penetration testing consists of an IT professional mimicking the actions of a malicious cybercriminal to determine whether an organization’s workplace technology possesses any vulnerabilities and can withstand their attack efforts. Conducting a penetration test can help your organization review the effectiveness of workplace cybersecurity measures, identify the most likely avenues for a cyberattack and better understand potential weaknesses.

Review this guidance to learn more about what penetration testing is, the benefits of such testing and best practices for carrying out a successful test within your organization.

What Is Cybersecurity Penetration Testing?

Put simply, penetration testing refers to the simulation of an actual cyberattack to analyze an organization’s cybersecurity strengths and weaknesses. This testing usually targets a specific type of workplace technology, such as the organization’s network(s), website, applications, software, security systems or physical assets (e.g., computers and smart devices). Penetration testing can leverage various attack methods, including malware, social engineering, password cracking and network hacking, among others.

Generally speaking, penetration testing is often performed by a professional from a contracted IT firm who is not associated with the organization being assessed in any way. This helps the cyberattack simulation seem as authentic as possible. Penetration testing is typically either external or internal in nature. The primary differences between these forms of testing are as follows:

  • External penetration testing requires the IT expert to attack an organization’s external-facing workplace technology from an outside perspective. In most cases, the IT professional won’t even be permitted to enter the organization’s physical establishment during external penetration testing. Rather, they must execute the cyberattack remotely—often from a vehicle or building nearby—to imitate the methods of an actual cybercriminal.
  • Internal penetration testing allows the IT expert to attack an organization’s internal-facing workplace technology from an inside perspective. This form of testing can help the organization understand the amount of damage that an aggrieved employee could potentially inflict through a cyberattack.

In addition to these testing formats, there are also two distinct types of penetration tests. How much information an organization provides the IT professional prior to the cyberattack simulation will determine the penetration test type. Specifically:

  • An open-box test occurs when the IT expert is given some details regarding the organization’s workplace technology or cybersecurity protocols before launching the attack.
  • A closed-box test occurs when the IT expert is provided with no details other than the organization’s name before conducting the attack.

Ultimately, the penetration testing format and type should be selected based on the particular workplace technology elements or cybersecurity measures that an organization is looking to evaluate.

Benefits of Cybersecurity Penetration Testing

Penetration testing can offer numerous advantages to your organization, including:

  • Improved cybersecurity evaluations—By simulating realistic cyberattack situations, penetration testing can help your organization more accurately evaluate its varying security strengths and weaknesses—as well as reveal the true costs and of any security concerns.
  • Greater detection of potential vulnerabilities—If any of your workplace technology or other cybersecurity protocols fail during a penetration test, you will have a clearer picture of where your organization is most vulnerable. You can then use this information to rectify any security gaps or invest further in certain cyber initiatives.
  • Increased compliance capabilities—In some sectors, organizations are legally required to engage in penetration testing. For example, the Payment Card Industry Data Security Standard calls for organizations that accept or process payment transactions to execute routine penetration tests. As such, conducting these tests may help your organization remain compliant and uphold sector-specific expectations.
  • Bolstered cybersecurity awareness—Mimicking real-life cyberattack circumstances will highlight the value of having effective prevention measures in place for your employees, thus encouraging them to prioritize workplace cybersecurity protocols.

Cybersecurity Penetration Testing Best Practices

Consider these top tips for executing a successful penetration test within your organization:

  • Establish goals. It’s crucial for you to decide what your organization’s goals are regarding the penetration test. In particular, be sure to ask:
    • What is my organization looking to gain or better understand from penetration testing?
    • Which cybersecurity threats and trends are currently most prevalent within my organization or industry? How can these threats and trends be applied to the penetration test?
    • What specific workplace technology elements or cybersecurity protocols will the penetration test target?
  • Select a trusted IT professional. Consult an experienced IT expert to assist your organization with the penetration test. Make sure to share your organization’s goals with the IT professional to help them understand how to best execute the test.
  • Have a plan. Before beginning the penetration test, work with the IT expert to create an appropriate plan. This plan should outline:
    • The general testing timeframe
    • Who will be made aware of the test
    • The test type and format
    • Which regulatory requirements (if any) must be satisfied through the test
    • The boundaries of the test (e.g., which cyberattack simulations can be utilized and what workplace technology can be targeted)
  • Document and review the results. Take detailed notes as the penetration test occurs and review test results with the IT expert. Look closely at which cybersecurity tactics were successful during the attack simulation and which measures fell short, as well as the consequences of these shortcomings. Ask the IT professional for suggestions on how to rectify security gaps properly.
  • Make changes as needed. Based on penetration test results, make any necessary adjustments to workplace technology or cybersecurity protocols. This may entail updating security software or revising workplace policies.
  • Follow a schedule. Conduct penetration testing at least once every year, as well as after implementing any new workplace technology.

We can help you recover from a cyber attack

Businesses are operating in an environment where it’s not a matter of IF a cyber attack will occur, it’s only a matter of when.

We need to take reasonable measures to reduce the likelihood of an attack, but we also need to be realistic and understand that inevitably, we’ll all deal with a cyber attack at some point.

The two most important questions you need to answer as a business owner are:

  1. Will I know how to respond when a cyber attack occurs?
  2. Will my business survive the devastating consequences of a cyber attack?

The planning you do today, the strategic partnerships you put in place, and the adequacy of your Cyber & Data Breach Insurance coverage are all critical components to confidently answering the question of ‘will my business survive after a cyber attack’ with a resounding ‘ABSOLUTELY.’

We understand the negative effects a cyber attack can have on your organization, we’ve seen first-hand how it impacts clients. We also know which insurance companies provide the broadest insurance coverage to help you recover after an attack occurs.

But we don’t stop there.

The best place to begin is with your own internal operations, the security measures you have in place, the controls implemented to avert a data breach and the response plans if a breach occurs.

In addition providing the Cyber & Data Breach Liability coverage, we can also provide you several services that will help position your business for the best insurance premiums offered by the nation’s strongest insurance carriers.  Specifically, we can:

  • Provide you with data security resources designed to help keep your data, and your network, safe
  • Perform a cyber risk assessment of your business to help identify areas of weakness, and offer solutions to mitigate the exposures
  • Help you develop and implement an incident response plan

To learn more about the ways we can help simply Request a Proposal and we’ll get to work right away.

Tom Simon

Tom Simon

Chairman of the Board

Tom has worked in the insurance industry since 1977 holding numerous positions from Account Executive and Agency Manager, President to his current role. He combines his unique ability of thinking differently with his wealth of insurance and business experience to propel CoverLink to new levels of success.

In his spare time, he enjoys spending time with his family, especially his grandkids. In addition, he’s also an avid woodsman… yes, you read that correctly. He can often be found yelling “timber” or just splitting firewood for family and friends.

 

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Matt Simon

President

Prior to joining the team at CoverLink in 2006, Matt worked as an Underwriter with a multi-state insurance company located in Columbus, Ohio. Matt is a Certified Insurance Counselor (CIC) and Chartered Property and Casualty Underwriter (CPCU), having successfully completed the rigorous coursework and exams to earn these designations.

He also serves on the Board of Directors for the Ohio Insurance Agents Association and the Associated Risk Managers of Ohio, in addition to volunteering his time to multiple other community and industry organizations.

In 2013, Matt was awarded and recognized as the National Young Insurance Agent of the Year, and in 2019 he was recognized as the Insurance Advisor of the year by Finance Monthly.

 

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Gina Loehr

Gina Loehr

Senior Account Manager

Gina oversees the Commercial Lines division at CoverLink, which is responsible for managing the business insurance needs for clients.

She has worked in the insurance industry since 1980, beginning as a Commercial Underwriter with a regional company located in Springfield, Ohio.

In 1984, she earned her Certificate in General Insurance, and in 1995, her Accredited Advisor of Insurance designation.

In her spare time, she enjoys spending time with her family, including four grandkids, and biking.

 

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Kyle Carper

Account Manager

Kyle joined the CoverLink team in 2018 as in intern when he was a junior in high school. Shortly after, he began studying to obtain his insurance license, which he passed in 2020 and joined our Personal Lines division.

Kyle helps individuals and families with their home, auto, umbrella and other personal insurance needs, which he thoroughly enjoys.

In his spare time, he enjoys spending time with the ones he loves, watching sports and playing video games.

 

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Tim O’Rielley

Senior Insurance Advisor

Tim works with individuals, families and businesses to design insurance policies perfectly suited to their specific needs.

He has been working in the insurance industry, and with CoverLink, since 1993. As a lifelong resident of Logan County, he’s been involved with a number of community organizations, often taking the leadership role such as President of the Chamber of Commerce, and the United Way.

He’s often found spending as much time as possible with his two daughters, and his grandkids

 

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Mark Osborne

Account Executive

Mark has worked at CoverLink since 2004. He specializes in life and health insurance, where he utilizes his extensive knowledge to help clients make sense of a confusing and ever changing market.

He also holds the Property & Casualty Insurance License, and often helps families as well as small businesses to set up their insurance protection plan.

Mark graciously volunteers his time to several community organizations, and enjoys spending his free time with his family

 

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Leah Loehr

Account Manager

Leah joined the Commercial Lines division at CoverLink in 2012 where she works closely with business owners on their Commercial Insurance needs to help them achieve their desired level of protection.

Leah is known for her outgoing personality, positive attitude, and relentless pursuit of the goals she sets out to achieve. Clients often rave about her and the service she provides.

In her spare time, Leah enjoys spending time with her family and friends… and she can often be found at the closest Buffalo Wild Wings!

 

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Larry Middaugh

Larry Middaugh, PLCS

Senior Insurance Advisor

Larry joined CoverLink with an extensive background in sales, bringing over 30 years of experience and commitment to taking care of his clients in the banking and mortgage industry.

Larry’s dedication to his clients aligned so well with the CoverLink tradition of relentlessly caring for, and protecting its clients, that he joined the team of Licensed Insurance Advisors in 2015.

Those in need of Personal or Business Insurance are delighted after working with Larry.

Larry defines success as knowing his purpose in life, continuing to grow to reach his fullest potential and sowing seeds that benefit others. He’s a father of three incredible children and husband to an amazing, kind and loving wife.

 

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Tony Fink

Tony Fink, CIC, CLCS

Insurance Advisor

Tony is responsible for serving the needs of individuals and businesses looking for property & casualty insurance. In addition, he’s licensed and capable of advising clients that desire life insurance protection.

He’s a Certified Insurance Counselor (CIC) and a Commercial Lines Coverage Specialist (CLCS), having successfully completed the rigorous coursework and exams to earn these designations.

Tony entered the insurance industry in 2008 bringing a diverse background of experience and knowledge to his Account Executive position with CoverLink.

In his free time, Tony enjoys spending time with his family, being outdoors, following sports and listening to music.

 

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Meg Barton

Meg Barton

Senior Account Manager

Meg works in the Commercial Lines division at CoverLink as an Account Manager, where she helps businesses with their varying & complex insurance needs, from Business Auto to Commercial Liability, Directors & Officers to Commercial Property.

Meg earned her Bachelor’s degree in Business Management from Urbana University in Ohio. She has been active in the insurance industry since 2006, and is an Ohio Notary.

In her spare time, Meg enjoys spending time with her family at Indian Lake, listening to live music and reading.

 

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Jordan Springs

Jordan Springs

Account Manager

Jordan joined the CoverLink team in 2017, bringing top-notch client service skills acquired through several years in the banking industry.

She’s constantly assisting and advising clients on their personal insurance needs – home, auto, jewelry, umbrella and other policies – not to mention, she’s just plain fun to be around!

In her spare time, Jordan enjoys spending time with family and friends, especially her husband and two kids.

 

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Jill Rawlins

Jill Rawlins

Account Manager

Jill works in the Personal Lines Department where she helps individuals and families with their Home, Auto, Umbrella and other personal insurance needs.

She graduated with her Bachelor’s Degree in 2009 from Otterbein University, and shortly after began her career in the insurance industry.

In addition to holding the Ohio Property & Casualty Insurance License, she also has her Accident & Health, Life and Variable licenses.

Jill enjoys spending as much time as she can with her family, and especially enjoys being with her little girl who makes her laugh often.

 

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Chris Badenhop

Chris Badenhop

Insurance Advisor

Chris joined the CoverLink team in 2017 with a diverse and exciting professional and educational background. He works with individuals, families and businesses to find the ideal solution for their insurance needs.

He brings a positive attitude and a desire to help his clients in his position as an Insurance Advisor, but most importantly, he shares one of the most fundamental beliefs we hold dear within our organization: he cares. He cares about his clients, he cares about protecting all that’s important to them, and above all, he cares about doing what’s in the best interest of his clients. His enthusiasm and empathy set him apart, and he’s backed by the top-notch service provided at CoverLink, making him a tremendous asset to his clients. In short, Chris puts people before policies.

In his free time Chris enjoys spending time in the outdoors hunting and fishing. He’s also a passionate sports fan devoting support to all levels of play.

 

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Joe Cooney

Joe Cooney

Senior Insurance Advisor

Shortly after graduating from John Carrol University in 2008, Joe began his insurance career. His original focus and expertise was on personal lines and small commercial accounts, but he has since expanded his focus to include Cyber Insurance and Life Insurance, among other products.

Joe resides in Fairview Park, Ohio with his wife Megan and young son Jack. In his spare time, he coaches youth basketball and volunteers for the special Olympics.

 

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Kelli Young

Kelli Young

Director of Marketing

Kelli brings extensive marketing expertise to CoverLink after spending nine years in the automotive industry, where she gained valuable insight in the areas of design, digital presence, and content creation.

After joining CoverLink in 2015, her focus has been on telling the story of our long standing belief, that people are more important than policies, in a fresh way with a digital twist, allowing consumers who believe what we believe to find us easier.

Kelli graduated from Ohio University in 2006 with a Bachelor’s Degree in Communications, and earned her Master’s Degree in Business from Ashland University in 2010.

She enjoys spending time with her family, especially being outside with her son and two daughters.

 

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Jami Radern

Jami Rader

Director of First Impressions

As the Director of First Impressions, Jami brings top-notch client service skills. She’s constantly assisting clients with billing inquiries, working to resolve any frustrating issues they’re having, and she’s just plain fun to be around!

In her spare time, Jami enjoys spending time with family, especially her husband and four children and going on four-wheeling trips together.

Erika Asher

Account Manager

Erika works in the Commercial Lines division at CoverLink as an Account Manager, where she helps businesses with their varying & complex insurance needs, from Business Auto to Commercial Liability, Directors & Officers to Commercial Property.

In her spare time, Erika enjoys hiking, reading, and spending time with her son.

 

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Erin Whitaker

Account Manager

Erin joined the Personal Lines division at CoverLink in 2019, as an Account Manager, where she helps individuals and families with their Home, Auto, Umbrella and other personal insurance.

She previously worked in the healthcare industry before getting her insurance license in November of 2018.

When Erin isn’t at work, you can find her cheering on her kids at various sporting events almost every day of the week. In addition, she enjoys planting flowers, finding rusty items to decorate with and spending as much time with her family as possible.

Alissa Grim

Alissa Grim

Account Manager

Alissa works as an Account Manager where she helps individuals and families find the insurance that best fits their needs.

In addition to earning her Ohio Property & Casualty Insurance license in 2008, Alissa received her Life Insurance License in 2010.

In her spare time, Alissa enjoys spending time with her family camping, and watching her son race go karts around the U.S.

Vickie Allen

Vickie Allen

Account Manager

Vickie has worked at CoverLink since 2000 helping clients with a diverse set of needs, from securing the coverage that’s best for their individual situation, to providing guidance when claims or billing questions arise.

Vickie currently holds the Ohio Property & Casualty Insurance License, and is well known to clients because of her infectious personality and radiant smile that greets them when visiting the office.

In her spare time she enjoys spending time with family and friends, and traveling.

Randy Leopard

Randy Leopard

Vice President

Randy began his insurance career in 2000 working with both personal and business clients on their health insurance needs.  In 2008, he expanded his area of focus to include all types of insurance his clients needed from home & auto insurance, business insurance and farm insurance.

Randy resides in Urbana where he enjoys spending time with his family, and watching his horses race from time to time.

Melodi Wilkins

Melodi Wilkins

Senior Account Manager

Melodi has called CoverLink her ‘work home’ since 2009.  In her position as a Senior Account Manager, she works closely with clients needing home, condo, renters, auto, umbrella and other types of personal insurance coverage. Melodi also provides service and assistance to businesses regarding their insurance protection needs.

In her spare time, Melodi enjoys being outside and spending time with her family, especially with her granddaughter.

Morgan Edwards

Morgan Edwards

Account Manager

Morgan joined the CoverLink family in 2019, as an Account Manager. She helps her clients with personal insurance needs such as, home, condo, renters, auto umbrella and more. In addition, she works closely with business owners on their Commercial Insurance needs to help them achieve their desired level of protection.

In her spare time, Morgan enjoys spending time with her family and friends, making memories and enjoying all that life has to offer!

Sam Ankrom

Insurance Advisor

Sam joined the Coverlink team in 2020 with a strong passion and drive to help people. As an insurance Advisor with his Property & Casualty license, he assists individuals and business with all of their insurance needs.

He is dedicated to going above and beyond for his clients and wants to make sure every client is not only properly insured, but can also feel like a part of the Coverlink family. Sam is committed to helping everyone feel confident and comfortable with their insurance decisions and have the peace of mind knowing they are taken care of by not only himself, but by the entire Coverlink team.

Outside of work you can usually find Sam spending time with friends and family, or outside on the golf course.