Careful Security careers

Careful Security is a boutique cybersecurity consulting firm that helps startups and mid-market companies turn compliance from a blocker into a business accelerator. We specialize in SOC 2, ISO 27001, HIPAA, and PCI-DSS — delivering managed vCISO services, compliance readiness programs, penetration testing, and MSSP capabilities that actually get companies audit-ready, not just checkbox-compliant.
Our clients range from Series A startups preparing for their first SOC 2 to established mid-market companies navigating complex multi-framework environments. We combine deep technical expertise with practical, business-focused guidance — because we believe cybersecurity isn't just defense, it's a competitive weapon.
We're also building Dashr.ai, our proprietary compliance readiness platform that gives companies real-time visibility into their security posture and audit preparedness.
What makes us different: we're small enough that every team member has direct impact on client outcomes and company direction, but growing fast enough that early hires will shape how we scale. We're on a path from $500K to $5M ARR and building the team and systems to get there.
We're remote-first, results-driven, and allergic to bureaucracy. If you want to do meaningful security work with real autonomy — not get buried in a large firm's org chart — Careful Security is where you build your career.