Cybersecurity Compliance Project Manager

About Us

Careful Security helps organizations turn cybersecurity and compliance into a business advantage. We pair expert vCISO guidance with AI-powered automation through our platform, Dashr.ai, to get clients audit-ready faster and keep them secure.

The Role

You are the operational backbone of our compliance practice. You own the templates, run the client meetings, and make sure every engagement runs on clear, repeatable processes. If you love bringing order to complexity and keeping clients confident, this role is for you.

This role starts part-time, or on contract, with a clear path to full-time as our practice grows.

What You’ll Do

• Build, document, and maintain our library of compliance templates (policies, procedures, risk assessments, audit evidence, reports)
• Lead client meetings: kickoffs, status updates, gap reviews, and audit prep sessions
• Design, document, and enforce internal processes so every engagement is consistent and scalable
• Manage project timelines, deliverables, and action items across multiple clients
• Track remediation progress and keep clients on schedule for certifications and audits
• Coordinate across our security, technical, and sales teams
• Continuously improve workflows using automation and AI tools

What You Bring

• 2+ years in project management, ideally in cybersecurity, GRC, or IT compliance
• Working knowledge of frameworks such as SOC 2, ISO 27001, HIPAA, NIST CSF, PCI DSS, or CMMC
• Excellent writing and documentation skills
• Confident, client-facing communicator who can run a meeting and drive decisions
• Highly organized, detail-oriented, and deadline-driven
• Comfortable with project management and GRC tools

Nice to Have

• PMP, CAPM, CISA, CISSP, CRISC, or Security+
• Consulting or MSP/MSSP experience
• Experience using AI tools to streamline documentation

Why Join

• Clear path to a full-time role and leadership of the compliance practice
• Flexible, remote schedule that fits around other commitments
• Performance bonus tied to client onboarding and audit milestones
• Build the playbook from the ground up, with your name on it
• Hands-on experience with AI-powered compliance tools (Dashr.ai)
• Compensation: $24–$30/hour, based on experience

To Apply

Send your resume and a short note on a process you built or improved. Please include your weekly availability and preferred arrangement (part-time or contract).