About Careful Security
Careful Security is a boutique cybersecurity and compliance implementation firm based in Burbank, CA. We deliver SOC 2, ISO 27001, ISO 42001, HIPAA, and PCI-DSS programs end-to-end, along with vCISO services, penetration testing, and our proprietary compliance monitoring platform, Dashr.ai. We back our work with a 90-day compliance readiness guarantee and a hands-on delivery model that sets us apart from generic GRC vendors.
We are scaling. We need a sales professional who can find the right buyers, open the door, and book qualified conversations.
The Role
You will own the top of our commercial pipeline. Your job is to identify security and compliance buyers, open conversations, qualify them against our offerings, and book qualified meetings into the CEO's calendar. Pipedrive is our single system of record and is non-negotiable.
What you will do:
- Run targeted outbound across email, LinkedIn, and phone into mid-market and SMB security buyers
- Build account lists by ICP: SaaS, fintech, healthtech, and AI-native companies pursuing SOC 2, ISO 27001, ISO 42001, HIPAA, or PCI-DSS
- Qualify against framework, timeline, budget authority, and audit window — book discovery calls for the CEO
- Maintain every contact, activity, deal stage, and note in Pipedrive in real time
- Nurture warm referral channels including CPAs, audit firms, cyber insurance brokers, and Provisors network connections
- Report a weekly scorecard: activities, meetings booked, pipeline added, and conversion rates
Who you are
Must have:
- 2+ years B2B outbound sales experience, ideally in cybersecurity, compliance, SaaS, or IT services
- Track record booking qualified discovery meetings with director-and-above buyers
- CRM-disciplined operator: Pipedrive, HubSpot, or Salesforce — every touch logged, every deal current
- Comfort selling to technical buyers (CISO, CTO, Head of Security, Compliance leads)
- Self-directed, curious, automation-minded, and comfortable with ambiguity
- Strong written and verbal English
Nice to have:
- Existing network in CPA, audit, or cyber insurance channels
- Familiarity with SOC 2, ISO 27001, or HIPAA buyer journeys
- Experience with Apollo.io, ZoomInfo, or similar prospecting tools
- Comfort with AI-assisted prospecting workflows
Compensation & Structure
- 1099 independent contractor engagement (LLC required after initial 90 days per California AB5 compliance)
- Monthly base retainer plus uncapped commission on closed-won revenue
- Performance checkpoints at 30 days, 90 days, and 6 months
- Existing client accounts and partner-sourced deals are subject to an exclusions schedule disclosed at offer
- Path to expanded scope and W-2 conversion based on performance
Location
Remote within the United States. You must be able to work core US business hours and overlap with Pacific Time for daily sales standups.
Careful Security is an equal opportunity employer. We evaluate qualified applicants without regard to race, color, religion, sex, sexual orientation, gender identity, national origin, disability, veteran status, or any other protected characteristic.