---
title: 'Manager of Information Technology at OpenSesame'
canonical: 'https://feeny.ai/job/manager-of-information-technology-opensesame-remote-gavasaf8gsmz'
type: 'job'
last_seen: '2026-09-05'
---

# Manager of Information Technology at OpenSesame

- **Company:** OpenSesame
- **Location:** Remote
- **Work type:** remote
- **Posted:** 2026-08-31
- **Last confirmed live:** 2026-09-05
- **Apply:** https://boards.greenhouse.io/opensesame/jobs/8167583?gh_jid=8167583

## Job description

## 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:https://www.opensesame.com/about[www.opensesame.com/about](https://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.

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 built systems, driven alignment, and created impact at scale. When you look back a year from now, you’ll know you’ve made OpenSesame better, faster, and stronger because of your leadership.

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 $120,000 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.

Benefits: Benefits include comprehensive medical, dental, and vision coverage, flexible PTO, 401(k) matching, incentive stock options, volunteer time off, Employee Resource Groups, and a generous professional development program with dedicated annual time off for learning and growth.

We use AI. For real. Every team at OpenSesame works with AI tools daily, not as a buzzword, but as practice. You'll build fluency that most companies are still talking about adopting, with hands-on training and clear guardrails to experiment responsibly. AI amplifies your creativity and judgment. It doesn't replace them. The skills you build here travel with you.

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](https://www.opensesame.com/privacy) or the California Attorney General's website.

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.

## About OpenSesame

## Company Overview
- **One-liner**: OpenSesame provides a curated online training platform with over 60,000 courses in 70+ languages, helping organizations retrain their workforce for the age of AI.
- **Entity Type**: Private (Series D)
- **Headquarters**: Portland, Oregon, USA (remote-first)
- **Founded**: 2011
- **Founders**: Not publicly available (CEO is Don Spear)

## Core Business
- **Primary industry**: Corporate e‑learning / EdTech
- **Target customers**: B2B – enterprises, mid‑market, and SMBs that need compliance, skills, and workforce‑reinvention training
- **Mission**: “Workforce Reinvention in the age of AI” – integrated software, curated content, and expert services embedded into existing HR and learning systems.

## Products & Services
- **OpenSesame Platform**: SaaS‑based learning management and course curation with 60,000+ pre‑vetted courses matched to roles, skills, and strategy.
- **Simon (AI‑assisted custom course builder)**: Enables subject‑matter experts to build custom courses in under an hour using AI and learning science.
- **Workforce Reinvention Executive Series**: Expert‑led guidance for CHROs on leading AI‑driven workforce transformation safely and at scale.

## Market Standing
- **Valuation/Market Cap**: Not disclosed
- **Key Metric**: Annual Revenue ~$29M (estimated); Total Funding $97M
- **Notable Investors/Partners**:
  - JMI Equity (lead, Series D – $50M in 2021)
  - Altos Ventures, Partech, FTV Capital
- **Growth Signals**: 226 employees; remote‑first global team across 9 countries; active job postings +33% monthly; strong LinkedIn following (21,671); product reviews 4.7/5; CEO Don Spear driving “Workforce Reinvention” narrative.

## Competitive Advantages
- Largest pre‑vetted course library (60,000+) in 70+ languages with human curation and AI shortcuts.
- Fully embedded into existing HR/LMS systems (integrated software, not a standalone tool).
- AI‑powered custom course builder (Simon) reduces time from expert knowledge to course from weeks to under an hour.
- Remote‑first culture that attracts global talent and lowers attrition.

## Strategic Focus
- “Workforce Reinvention” in the AI era – helping CHROs and people leaders upskill and reskill employees safely and responsibly at scale.
- Deepening AI capabilities (AI‑assisted curation, custom course generation) while maintaining quality and compliance.
- Geographic expansion and hiring across Engineering, Data, AI, and Sales roles.

## Why Work Here
- **Remote‑first culture**: Live and work where you thrive; offices in Portland and Austin, but most roles are fully remote.
- **Comprehensive benefits**: Medical, dental, vision; 401k with 100% match up to 4%; flexible PTO; paid sick leave.
- **Professional development**: Every employee receives 40 hours/year and a generous budget for learning.
- **Volunteer Time Off (VTO)**: One day per year to give back.
- **Inclusion & ERGs**: Active Employee Resource Groups with annual ERG Week.
- **Recent ratings**: 3.7/5 on employer review sites (work‑life, compensation, culture, career).

## Sources
1. [opensesame.com/about/careers](https://www.opensesame.com/about/careers)
2. [opensesame.com](https://www.opensesame.com/)
3. [linkedin.com/company/opensesame](https://www.linkedin.com/company/opensesame)
4. [builtin.com/company/opensesame](https://builtin.com/company/opensesame)

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