We believe that privacy and security is so much more than checking a box

ClearOPS stands for clear operational privacy and security.

Our Story

In 2011, Caroline left the firm to join a startup as their first General Counsel. Initially, she focused on supporting sales and mastering privacy. It did not take long for sales to send her a security questionnaire. This check-the-box, security theater spreadsheet reminded her of her first summer job at a law firm. The first day on that job, she was instructed to sort through about 15 boxes of "due diligence." Her only instruction was to look for things that seemed odd. She realized that security questionnaires were similarly time-consuming and mind numbing, yet full of potential liability.

Several years later, she met George at an old NY coffee shop called Eisenberg's. George was a good friend with one of Caroline's colleagues, with whom she was having coffee. George joined the discussion and the two completely geeked out on privacy and security. George had a passion for security and online anonymity, having spent the last 20 years building networks and infrastructure for financial services.

As George and Caroline continued talking, the two frequently discussed the huge communication gap within companies about the privacy and security operations and how detrimental this was to business, ultimately hurting the individual user. They decided to start a company with a mission to give individual's their control back by bridging that communication gap. When George asked what they should start with, Caroline responded, "let's start with the response side to security questionnaires."

We are subject matter experts since
before big data was big
We have analyzed over
questions and answers
We collect over
We are committed to

Get To Know The Team

CEO Headshot

Caroline McCaffery

Ceo & founder
she/ her

"I am a woman, a lawyer, an entrepreneur and a privacy and security expert in the technology field. My career is all about glass ceilings."

CTO Headshot

George Rosamond

founder, cTo

"I never met a repetitive, laborious task that I didn't want to automate."

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Head of spr

"I'm a professional hacker who builds data gathering systems that foster transparency."


Aqsa Sheikh


"I research and write programs that understand why questions are asked and how the answers relate."

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Want to see if automating your questionnaires will save your business money? Check out our blog post on the cost of security questionnaires and fill in the information to our ROI calculator. It's our way of showing you just how much we can save your business.
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