Enterprise Cybersecurity Sales Executive - AI-Native

Pentera; Burlington (MA); On-site; USD 330,000 - 360,000; Full time

Benefits offered by this job

Competitive OTE

Benefits package

Job summary

Pentera is seeking an accomplished enterprise B2B salesperson to lead full-cycle deals in the cybersecurity space. You will source your own pipeline, engage CISOs with risk-based messaging, and close enterprise opportunities using AI-assisted tools.

You’ll help shape Go-To-Market motion and drive revenue across enterprise accounts. You’ll operate in a dynamic environment with Salesforce, Gong, Outreach, and AI-enabled workflows, delivering measurable business outcomes and scalable growth.

Qualifications

• 5+ years of enterprise B2B sales - cybersecurity or security buyers strongly preferred.
• Proven quota attainment on full-cycle enterprise deals, first touch to close.
• A self-sourced pipeline track record: you open your own doors and build demand.
• Credible CISO-level selling - risk and outcomes, not decks and scripts.
• Proficient with the AI-assisted sales stack: Salesforce, Gong, Outreach/Apollo, Sales Navigator, AI tools.

Responsibilities

• Own the full sales cycle end to end - prospecting, discovery, demos, POCs with our Sales Engineers, negotiation, close - across enterprise accounts.
• Self-source your pipeline: open your own doors and create demand - don’t wait for it.
• Sell to CISOs and security leaders, anchoring every conversation to their business risk, not our feature list.
• Run a modern, AI-assisted sales motion: Salesforce, Gong, Outreach/Apollo, Sales Navigator, and AI tools to research and personalize at scale.
• Forecast honestly and keep your pipeline clean - no deal goes dark without a clear next step.
• Shape the motion, not just run it - what you hear from buyers feeds Product, Marketing, and the playbook.

Skills

Enterprise B2B sales

Quota attainment

Self-sourced pipeline

CISO-level selling

AI-assisted sales tools

Tools

Salesforce

Gong

Outreach

Apollo

Sales Navigator

AI tools

Job description

Pentera is seeking an accomplished enterprise B2B salesperson to lead full-cycle deals in the cybersecurity space. You will source your own pipeline, engage CISOs with risk-based messaging, and close enterprise opportunities using AI-assisted tools.

You’ll help shape Go-To-Market motion and drive revenue across enterprise accounts. You’ll operate in a dynamic environment with Salesforce, Gong, Outreach, and AI-enabled workflows, delivering measurable business outcomes and scalable growth.