David Winn

Compliance Director

David Winn serves as the Compliance Director for Compliance Cavalry and Help Desk Cavalry (HDCav), bringing more than 25 years of IT leadership, cybersecurity expertise, and compliance experience to organizations throughout the Pacific Northwest. Since joining Team Cavalry in 2020, David has helped organizations navigate increasingly complex cybersecurity and regulatory requirements while building practical, sustainable compliance programs that support long-term business success.

Before joining HDCav, David spent close to two decades as the Director of IT, where he led enterprise IT operations supporting industrial and defense-related environments. His background in operational IT leadership gives him a unique ability to bridge the gap between compliance requirements and real-world business operations.

David holds a Bachelor of Business Administration from Pacific Lutheran University and maintains several advanced cybersecurity and compliance certifications, including:

  • Certified CMMC Assessor (CCA)
  • Certified CMMC Professional (CCP)
  • Registered Practitioner (RP)
  • CompTIA Security+ CE

David has become a trusted compliance leader within the CMMC ecosystem, helping organizations prepare for assessments, strengthen cybersecurity maturity, and develop scalable compliance strategies aligned with NIST and CMMC requirements. He has also served as a primary liaison during formal assessment engagements, including environments that achieved perfect 110-point assessment scores.

Beyond technology and compliance, David is deeply connected to the Kitsap community. He is a past Kingston High School Athletic Booster President, was an active member of the Kingston Rotary where he is also a past President, and a longtime supporter of local community events and volunteer programs. Whether supporting local fundraisers, participating in Adopt-a-Highway cleanups, or helping at community events, David reflects the Team Cavalry belief that strong businesses should also strengthen the communities they serve.

When he’s not helping organizations navigate cybersecurity and compliance challenges, David enjoys spending time with his wife gardening, cooking, pickling, and exploring new culinary projects.”