In this episode of The New CISO, host Steve Moore speaks with Dean Sapp, CISO and Data Protection Officer at Filevine, about one of security's most critical yet overlooked skills—written communication. Drawing from a brutal college English class that failed students for a single typo and over 20 years building security programs in the legal tech industry, Dean reveals why the ability to articulate security findings clearly separates average professionals from exceptional leaders who drive real business impact.
After abandoning architecture when he learned it would take six years to become licensed, Dean leveraged his dual skills in computer-aided drafting and IT to launch a career at Novell, eventually earning nine certifications in two years and a master's degree from SANS Institute. His background in design thinking shapes how he approaches security program development—viewing it like building a structure that requires solid foundations, functional systems, and even window dressing like SOC 2 compliance.
After interviewing over 100 candidates for SOC positions, Dean identifies the biggest missing skill as the inability to translate security findings into business language executives understand and act upon. He introduces the BLUF (Bottom Line Up Front) principle from military communications, explaining why security professionals have roughly eight seconds to capture executive attention. Dean champions radical transparency through simple frameworks—using stoplight systems or report card grades to communicate security posture, deliberately giving his own program failing marks in areas needing improvement to build trust.
Dean tackles operational communication breakdowns that create real security risk, emphasizing mandatory peer review before escalating incidents. This two-person rule dramatically improves report quality while reducing false positives that waste senior leadership time. He shares how this high-standards approach helped Filevine achieve best-in-class cyber insurance rates, with underwriters calling their security program superior to any SaaS provider they'd evaluated. Drawing on Erik Durschmied's "The Hinge Factor," he illustrates how small communication failures doom missions—just as cavalry troops charging cannons failed because not one rider carried the nails and hammer needed to disable them.
Throughout the discussion, Dean emphasizes holding yourself to impossibly high standards so that external auditors find you excellent. He advocates for brutal honesty about program gaps, documenting accepted risks clearly, and using tools like Grammarly Premium to improve writing quality. His philosophy combines military precision, architectural thinking, and pedagogical discipline—all in service of making security programs that actually work rather than just looking good on paper.
Key Topics Discussed:
* Why written communication is security's most critical missing skill
* BLUF (Bottom Line Up Front): Capturing executive attention in 8 seconds
* Using stoplight or report card systems for transparent board reporting
* Giving your security program honest grades to build executive trust
* Mandatory peer review before escalation to reduce false positives
* How Filevine achieved best-in-class cyber insurance rates
* The two-person rule for improving incident report quality
* Lessons from "The Hinge Factor" about preparation and tools
* Holding impossibly high standards so external auditors find you excellent
* Translating technical findings into business impact language
LEARN MORE:
👉 LinkedIn: https://www.linkedin.com/in/deansapp
Company Website: https://www.filevine.com
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