Senior Security Analyst - OpenSesame

About OpenSesame

OpenSesame is the trusted partner for Workforce Reinvention in the age of AI. OpenSesame delivers integrated software, curated and customizable content, and expert services – embedded into existing learning, HR, and work systems – to help organizations expand their human+AI potential and thrive through change.

About the Role

As a Senior Security Analyst on our Compliance team, you will play a key role in strengthening OpenSesame’s security posture in a fast-moving, high-growth environment. We’re looking for someone who brings deep technical security expertise, a proactive mindset, and the ability to turn complex risks into practical, scalable solutions.

This role spans vulnerability management, penetration testing, bug bounty operations, cloud and application security, and audit readiness. You’ll partner across Engineering, DevOps, IT, and Compliance to improve security processes, support compliance efforts, and help ensure security is built into how we work, especially as we continue evolving our approach to AI security.

Performance Objectives

Establish Security Ownership & Technical Depth (0–6 Months)

• Develop a comprehensive view of OpenSesame’s external attack surface, vulnerabilities, and threat landscape by integrating signals from CrowdStrike, cloud environments (AWS, GCP), and application security tooling.
• Own external penetration testing engagements end-to-end, including vendor selection, scope design, execution oversight, remediation validation, and executive reporting.
• Build and operationalize a structured vulnerability management program, partnering with DevOps, Engineering, and IT to prioritize and remediate risk effectively.
• Stand up scalable evidence collection and control mapping workflows in Drata to improve audit readiness and reduce manual effort.
• Establish strong cross-functional relationships to embed security into engineering, infrastructure, and IT workflows from the outset.

Operationalize Continuous & AI-Aware Security (6–12 Months)

• Design and implement a continuous penetration testing program that complements annual third-party testing by leveraging automation, threat modeling, and targeted validation.
• Own and mature the bug bounty program by improving signal quality, triage processes, researcher engagement, and remediation workflows.
• Lead implementation of AI security practices across internal systems and product development:
  • Apply OWASP Top 10 for LLMs / AI systems to identify and mitigate emerging risks
  • Support adoption and operationalization of ISO 42001 controls
  • Define secure usage patterns for internal AI tools and third-party AI integrations
• Partner with Product Engineering to define and enforce secure AI and application baseline requirements, ensuring security is built into system design.
• Develop automations and tooling (Python, APIs, Make) to continuously collect threat intelligence, validate security baselines, and detect drift across AWS, GCP, GitHub, and SaaS platforms.
• Improve Jira and Confluence workflows to create visibility, accountability, and measurable progress across security findings and remediation.
• Provide deep technical support during audits by translating real-world implementations into clear, defensible narratives aligned with ISO 27001, ISO 27701, and ISO 42001.

Drive Security Maturity & Compliance Integration (12+ Months)

• Serve as a senior technical partner to Compliance, supporting vendor reviews, customer security questionnaires, and control design with practical, implementation-level expertise.
• Continuously improve Drata automation and evidence pipelines to move toward near real-time compliance visibility.
• Partner with Engineering and DevOps leadership to evolve secure development practices, CI/CD security controls, and cloud security baselines.
• Establish and refine AI security governance models that balance innovation with risk management across internal and customer-facing use cases.
• Identify systemic risks, recurring vulnerability patterns, and process inefficiencies to drive durable, organization-wide improvements.
• Contribute to long-term security strategy, aligning threat management, AI adoption, compliance requirements, and engineering velocity.

What Success Looks Like

• Penetration testing (external and continuous) is predictable, effective, and drives measurable reductions in risk.
• Vulnerabilities are prioritized intelligently and remediated within defined SLAs, with clear ownership across teams.
• The bug bounty program consistently yields high-quality findings with efficient triage and response.
• AI systems and tools are deployed with clear security guardrails aligned to OWASP AI Top 10 and ISO 42001.
• Engineering teams proactively incorporate security into design and development workflows.
• Audit readiness becomes continuous rather than event-driven, with strong evidence pipelines in Drata.
• Security is viewed as a strategic enabler of safe innovation, not a bottleneck.

Location & Travel

This position can be based anywhere in the US. We operate as a remote-first company and invest in mandatory all-company meetings several times a year in addition to required team travel as necessary (up to 15 days of travel per year).

Compensation & Benefits

• Base Salary: $130,000 – $190,000 depending on experience
• Benefits: Comprehensive medical, dental, and vision coverage
• Equity: Incentive stock options (ISOs)
• Retirement: 401(k) matching
• Time Off: Flexible PTO and volunteer time off
• Growth: Generous professional development program with dedicated annual time off for learning