Part-Time v-CISO Service Lead (1099 Contractor)

DataSure24 is seeking a seasoned cybersecurity professional to serve as our Virtual Chief Information Security Officer on a 1099 independent contractor basis. This is a part-time retainer engagement - not a full-time hire - designed for a senior practitioner who runs an independent security consulting practice and can dedicate 10-20 hours per month to our organization., We are seeking a proactive and experienced Part-Time v-CISO Service Lead (1099 Contractor) to guide our clients’ cybersecurity strategies and initiatives. In this role, you will serve as a virtual Chief Information Security Officer (v-CISO) for our clients, providing expert leadership on security policies, risk management, and compliance frameworks. Your energetic approach will help organizations strengthen their security posture through strategic planning, technical guidance, and incident response oversight.

SCOPE OF WORK

The Fractional CISO will be responsible for:

• Security Program Leadership - Own and evolve our information security strategy, policies, and roadmap aligned to business objectives.

• Risk & Compliance Management - Lead our compliance posture across applicable frameworks (DFS / SOC 2 / HIPAA / ISO 27001 / PCI-DSS - specify yours); manage the risk register.

• Board & Executive Reporting - Deliver security briefings to the board/audit committee; translate technical risk into business language.

• Vendor & Third-Party Risk - Oversee vendor security assessments, BAAs, DPAs, and annual third-party risk reviews.

• Incident Response Oversight - Own the IR plan, tabletop exercises, and serve as executive lead during security incidents.

• Security Awareness - Direct the annual security awareness training program and phishing simulation cadence.

• Penetration Testing & Vulnerability Management - Scope and oversee annual pen tests; review results and remediation roadmaps.

• Policy & Standards - Maintain, update, and communicate information security policies, standards, and procedures.

• Team & Vendor Guidance - Provide strategic direction to internal IT/security staff and managed security service providers (MSSPs).

• M&A / Due Diligence Support - Provide security input on partnerships, acquisitions, or new product launches as needed.

Do you have experience in Team leadership?, * 10+ years of information security experience, including at least 3 years in a CISO, VP of Security, or equivalent leadership role.

• CISSP, CISM, CRISC, or equivalent certification.

• Demonstrated experience operating as a fractional, interim, or independent consulting CISO - we want a practitioner who knows this model.

• Deep expertise in at least two of: SOC 2, ISO 27001, HIPAA, PCI-DSS, CMMC, NIST CSF.

• Experience presenting to boards of directors and executive leadership teams.

• Ability to work independently, manage multiple client relationships, and deliver without daily oversight.

• Active LLC, sole proprietorship, or corporation; able to provide a W-9 and Certificate of Insurance before engagement start.

• Strong written and verbal communication skills - you will be the face of security to our leadership and customers.

PREFERRED QUALIFICATIONS

• Prior experience in SaaS / healthcare / financial services.

• Hands-on experience with GRC platforms (Vanta, Drata, OneTrust, Archer, or similar).

• Cloud security expertise in AWS, Azure, or GCP - Security Hub, Defender for Cloud, IAM governance.

$100 - $125 an hour - Part-time, Pulled from the full job description

• Flexible schedule, * Competitive hourly rate

• Long-term, stable engagement with a growing organization - not a one-time project.

• Collaborative internal team (IT, Engineering, Execuitve) ready to execute on your direction.

• Flexibility to manage your own schedule; we care about outcomes, not hours logged.

• Opportunity to grow with us - as we scale, so may the scope of this engagement.