Manager of Information Technology

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.
• Authentic