About OpenSesame 

OpenSesame is disrupting the workforce development industry, leveraging an AI-powered marketplace of more than 50,000 skills courses, complemented by assessments, content authoring, curation, personalized learning pathways, and virtual coaching. eLearning is delivered seamlessly through existing enterprise systems and in the flow of work. More than 2,000 companies, including 150+ of the Global2000, rely on OpenSesame to develop the world’s most productive and admired workforces.

www.opensesame.com/about

About the Team

The IT team at OpenSesame keeps our employees productive by providing responsive, high-quality technical support. We work across the organization to resolve issues quickly, manage systems efficiently, and continuously improve the employee technology experience. Our team values collaboration, customer focus, and reliability.

About the Job

As a Help Desk Support Specialist, you’ll be the first point of contact for resolving technical issues, managing user access, and setting up hardware and software. You’ll support employee onboarding, maintain support documentation, and help ensure smooth day-to-day operations. This role requires strong communication skills, ownership of issues through resolution, and the ability to support non-technical users in a fast-paced, primarily remote environment.

Performance-Based Objectives

Within 30 Days

• Complete onboarding and demonstrate proficiency with OpenSesame’s ticketing system, IT documentation tools, and support workflows.
• Shadow hardware and software deployment activities, including workstation setup and user account provisioning.
• Resolve at least 20 Tier 1 IT support tickets, ensuring adherence to internal documentation and defined SLA standards.

Within 60 Days

• Independently resolve an average of 15 IT support tickets per week, handling hardware, software, and login-related issues.
• Complete 100% of user account requests within one business day of receipt.
• Update at least 3 knowledge base articles internal documentation to reflect current procedures and reduce repeat support requests.

Within 90 Days

• Increase to an average of 30 resolved support tickets per week, maintaining a 90% SLA compliance rate for Tier 1 tickets.
• Lead at least one IT onboarding session for a new employee, covering essential tools and support processes.
• Identify at least one recurring technical issue, document its impact, and propose a prevention or resolution plan in collaboration with Systems Engineering where appropriate.

Within 120 Days

• Sustain an average of 50 resolved support tickets per week, balancing ticket resolution with onboarding support and documentation responsibilities, with consistent SLA adherence and positive user feedback.
• Deliver a peer training session on a key IT tool, application, or support process.
• Actively contribute to one internal IT process improvement initiative, such as refining the hardware setup checklist or enhancing the triage system.

By 6 Months

• Demonstrate full autonomy in managing Tier 1 support, including hardware/software troubleshooting and user lifecycle management.
• Serve as a backup for onboarding/offboarding duties and support escalations.
• Maintain high accuracy and completeness in logging and closing tickets in the system, and continue contributing to team knowledge-sharing and documentation.
• Maintain strong end-user satisfaction through clear, timely, and effective communication.

Tech Stack

• OKTA
• Apple Macbook
• Google Workspace (GSuite)
• Jira
• Confluence
• Zoom
• Microsoft Intune
• JAMF
• Password Manager

Location: This is a remote-first role based in Mexico. 

Performance Driven: We're looking for self-starters with a track record of delivering excellent results, and we're highly selective about who we hire. We don't focus on typical job requirements, instead, we're interested in specific examples from your past experiences.

Pay Transparency: At OpenSesame, we prioritize pay transparency, fairness, and equity to create a positive and inclusive work environment, regularly reviewing our compensation practices to align with our values and goals. We provide competitive and fair compensation to our employees based on their skills, experience, and performance. 

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.

Learn more: www.opensesame.com/about

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. We’re looking for proven examples from your career that show you can do this job; that you’ve owned penetration testing programs, built vulnerability management systems, implemented security automation, and helped organizations adopt modern technologies (including AI) securely and responsibly.

You’ll be a strong fit if you’re detail-oriented, collaborative, and excited to build programs that reduce risk, improve visibility, and support safe innovation across the business.

Performance Objectives

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

• Develop a comprehensive view of OpenSesame’s external attack surface, vulnerabilities, and threat landscape — 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 — improving audit readiness and reducing 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 — leveraging automation, threat modeling, and targeted validation.
• Own and mature the bug bounty program — 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, not retrofitted.
• 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 — 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 — moving 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 — balancing innovation with risk management across internal and customer-facing use cases.
• Identify systemic risks, recurring vulnerability patterns, and process inefficiencies — driving 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 — including AI 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.

You might notice we don’t have the typical list of requirements and buzzwords here. That’s intentional.

We’re looking for proven examples from your career that show you can do this job — that you’ve owned penetration testing programs, built vulnerability management systems, implemented security automation, and helped organizations adopt modern technologies (including AI) securely and responsibly.

When you look back a year from now, you’ll know you’ve made OpenSesame more secure, more resilient, and better positioned to innovate with confidence.

Although it should go without saying (but it doesn’t), OpenSesame is an equal opportunity employer and we strive to create a welcoming, inclusive environment that celebrates diversity.

Location: 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.

Performance Driven: We're looking for self-starters with a track record of delivering excellent results, but we're highly selective about who we hire. We don't focus on typical job requirements, instead, we're interested in specific examples from your past experiences. All positions can be based anywhere in the US, and require up to 15 days of travel per year, with senior management and leadership teams requiring up to 35 days.

Compensation: The base salary for this position generally ranges between $130,000 and $160,000, depending on experience. At OpenSesame, we offer a comprehensive benefits package to employees upon hire, including professional development, ISOs, health insurance, 401(k) matching, and paid time off. 

Equal Employment Opportunity: OpenSesame is an Equal Employment Opportunity and Affirmative Action employer that values and welcomes diversity. We do not discriminate on the basis of various legally protected characteristics, including criminal history, and strive to provide reasonable accommodations to qualified individuals with disabilities. We prioritize safety and security and may use your information accordingly, and you can contact us for assistance or accommodations during the job application process. 

Pay Transparency: At OpenSesame, we prioritize pay transparency, fairness, and equity to create a positive and inclusive work environment, regularly reviewing our compensation practices to align with our values and goals. We provide competitive and fair compensation to our employees based on their skills, experience, and performance.

CPRA (California Candidates): When you submit your application, OpenSesame may collect and use your personal information in accordance with our privacy policy and the CPRA. This may include personal details and employment history, and will only be used for employment-related purposes. We may share this information with third-party service providers, but we will not sell it to third parties. If you have any questions or concerns, please contact us, and for more information on your rights under the CPRA, refer to our privacy policy or the California Attorney General's website.

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.

Learn more: www.opensesame.com/about

About the Job

We are seeking a strong, organized IT leader who wants to take an existing helpdesk and sysadmin organization and elevate them from reactive support to a proactive, process-driven internal service organization.

This is a working manager role for someone who thrives at the intersection of:

• People leadership and coaching
• Project and roadmap ownership
• Process design and operational rigor
• Security-minded systems thinking

A key priority for this role is establishing a reliable, automated, and audit-ready employee onboarding and offboarding program that works flawlessly across departments. This leader will bring structure, accountability, and measurable improvement to IT operations while developing a high-performing team.

Performance Objectives:

In your first 90 days, you will be getting the lay of the land with both your teams and OpenSesame. Success at 90 days means you have clarity on gaps, a prioritized roadmap, and early momentum toward operational improvements.

• People:
  • Build strong relationships with team members and understand career goals.
  • Assess strengths, skill gaps, and coaching opportunities.
  • Understand your team’s process and how people work together.
  • Participate in regular team workflows to gain hands-on context.
  • Get to know your peers in compliance, engineering and across the company.
• Product:
  • Gain hands-on familiarity with core IT tools and workflows.
  • Develop a reasonable understanding of the company tool ecosystem and ensure documentation is up to date.
  • Ride along with a vendor evaluation and/or renewal
  • Coach team members in collectively owning their work.
  • Audit the current onboarding/offboarding process end-to-end.
• Process:
  • Review the team productivity and quality metrics and OKRs.
  • Assess helpdesk SLAs, ticket workflows, and project intake.
  • Identify bottlenecks, documentation gaps, and automation opportunities.
  • Develop a 6–12 month improvement roadmap.
  • Take the reins for the process overall and evolve it further.
  • Propose a structured, cross-functional onboarding/offboarding framework.

Within 6 months, your team is aligned, projects are moving predictably, and onboarding/offboarding is measurably improving.

• People:
• Develop senior team members into player-coaches.
• Establish clear ownership areas within the team.
• Improve visibility into team workload and capacity.
• Collaborate with compliance and engineering to have a shared security stance vision.
• Communicate about complex migrations with groups, potentially the entire company, at a high level of quality.
• Product:
• Own the IT project roadmap and prioritization process.
• Lead cross-functional IT initiatives (e.g., migrations, security improvements, system rollouts).
• Own 2-3 Vendor relationships.
• Begin to quantify vendor evaluation needs based on data.
• Collaborate and advocate for your vision for the project roadmap and priorities.
• Process:
• Own the application authentication stance for the company.
• Prioritize automation over hands-on action in more critical systems.
• Create disaster recovery processes for critical systems.
• Launch ongoing process improvement experiments backed by data.
• Implement measurable KPIs for onboarding/offboarding efficiency and accuracy.

By the end of your first year, you will have established yourself as a relied upon partner to most teams in OpenSesame and are working, often behind the scenes, for your team to keep them productively supporting all of the company's initiatives. IT runs with clarity and discipline.

• IT operates as a proactive partner, not just a service desk.
• You consistently understand team health, performance, and development needs.
• The team demonstrates ownership, accountability, and continuous improvement.
• Onboarding/offboarding is automated, documented, and audit-ready.
• Authentication and access management follow defined standards.
• Vendor spend and risk decisions are data-driven.
• Learning always, improving constantly.
• You are a trusted cross-functional partner influencing company-wide initiatives.

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.

Learn more: www.opensesame.com/about

About the Team

At OpenSesame, the Information Systems team empowers employees with the tools and systems to deliver exceptional customer service. We maintain Salesforce and key business platforms, streamline operations through automation, and enhance the employee experience through cross-functional collaboration.

About the Role

We’re seeking a motivated and detail-oriented Associate Business Systems Administrator to support our Salesforce platform and other core business systems. This is a great opportunity for someone eager to grow their technical skills, collaborate cross-functionally, and build a career within the Salesforce ecosystem.

As a key member of the Information Systems team, you’ll contribute to system administration, user support, process automation, and data management—helping ensure our systems run efficiently and our users are set up for success.

Performance Objectives: 

Within 30 Days:

• Gain a general understanding of OpenSesame’s Salesforce environment and business systems.
• Complete onboarding, familiarize yourself with existing automation, and support user management requests, such as role and profile adjustments.
• Complete routine administration tasks within 2 business days and process at least 5 minor system modifications.

Within 60 Days:

• Collaborate with other Salesforce administrators to identify process inefficiencies and recommend solutions.
• Assist in resolving user-reported Salesforce issues, ensuring at least 95% of business requests are implemented within agreed-upon timelines.
• Document and update system changes within 48 hours to ensure alignment with business processes.

Within 90 Days:

• Develop a standardized set of training materials and best practice guidelines for end users.
• Conduct at least one training session to improve adoption and efficiency.
• Take ownership of data imports, exports, and clean-up efforts, ensuring completion of data-related tasks within 2 business days.
• Participate in at least one significant process improvement that enhances system efficiency.

Within 120 Days: 

• Attend at least two training sessions or webinars per quarter to stay updated with the latest Salesforce releases and best practices.
• Work toward Salesforce Administrator certification, demonstrating a commitment to professional development.

Tech Stack

• Salesforce
• CPQ
• Jira/Confluence
• Ringlead
• Make
• Gong
• Celigo

Location: This is a remote-first role, but candidates must be located in regions that allow for significant overlap with U.S. time zones.

Performance Driven: We're looking for self-starters with a track record of delivering excellent results, and we're highly selective about who we hire. We don't focus on typical job requirements, instead, we're interested in specific examples from your past experiences.

Equal Employment Opportunity: OpenSesame is an Equal Employment Opportunity and Affirmative Action employer that values and welcomes diversity. We do not discriminate on the basis of various legally protected characteristics, including criminal history, and strive to provide reasonable accommodations to qualified individuals with disabilities. We prioritize safety and security and may use your information accordingly, and you can contact us for assistance or accommodations during the job application process. For more information on our Diversity, Equity, and Inclusion initiatives, click here.

Pay Transparency: At OpenSesame, we prioritize pay transparency, fairness, and equity to create a positive and inclusive work environment, regularly reviewing our compensation.

We Care About Your Security: We’ve been made aware of a phishing scam involving individuals impersonating OpenSesame recruiters. All legitimate communication from our team will come from @opensesame.com email addresses. If you receive a suspicious message, please contact us directly at careers@opensesame.com. Your security matters to us, thank you for staying vigilant.