The opportunity timeline

• Overview

  Strategic Advantage is hiring a Penetration Tester in Boston, MA.

• Role description

  Our next Penetration Tester will spend less time in meetings and more time in Emotional Intelligence, which is how Strategic Advantage prefers to operate. Earn $115,000 - $162,000 as a Penetration Tester, take ownership of Risk Assessment from day one, and build your career with a collaborative team.

  Key Responsibilities

  • Sketch the Burp Suite architecture, defend it in review, then build the thing
  • Pull Strategic Advantage's Kali Linux stack out of the MA region before the migration deadline
  • Deliver mid-level-quality features within the $115,000 - $162,000 Penetration Tester mandate
  • Build Burp Suite self-service tools so Boston teams stop filing tickets for everything
  • Mentor newer mid-level hires on how Strategic Advantage actually wires Kubernetes Security together
  • Shave milliseconds off the technology hot path that Strategic Advantage users feel every click
  • Reverse-engineer the mission-driven SOC 2 Compliance format Strategic Advantage inherited and never documented
  • Translate a napkin idea from Strategic Advantage founders into a Kali Linux people-first prototype

  What You'll Bring

  • Comfort presenting to a MA-wide audience without a script
  • A MA work history, or strong reasons you'll thrive here anyway
  • Strong time-management skills and a bias toward action
  • Ability to thrive both independently and as part of a tight-knit team
  • 5 or more years steering technology projects end to end

  The whole point of Strategic Advantage is to make GDPR Compliance dependable, and that plainspoken mission has anchored it in Boston from day one. Our Boston team would rather over-communicate than leave a teammate guessing at midnight.

  You'll receive $115,000 - $162,000, a hybrid schedule, and a personalized development plan tailored to your technology career goals.

  The Strategic Advantage team is scaling in Boston, MA, and we are hiring for it now.

  This temporary opening in Boston is built for someone like you, so don't let it pass.

• Required skills

  • Burp Suite
  • GDPR Compliance
  • Kubernetes Security
  • ISO 27001
  • Kali Linux
  • Risk Assessment
  • SOC 2 Compliance
  • Facilitation
  • Delegation
  • Emotional Intelligence

• Benefits & perks

  • Generous paid time off
  • Roth 401(k) option
  • Commission structure
  • Internet Reimbursement
  • Hackathons and innovation time
  • Free therapy and counseling sessions
  • Tuition reimbursement
  • Flexible Work Arrangements
  • Catered lunches
  • Burnout prevention resources
  • On-site cafeteria
  • Surrogacy assistance
  • Technology Stipend
  • Employer-paid health premiums
  • Career coaching

• Apply before 2026-12-18

  Submit your application for this Temporary technology position.