AI Engineer — Workforce Reinvention

About OpenSesame 

While it appears to most people that we just sell training courses (over 50,000 of them), what we really offer is the opportunity for companies to upgrade the skills of each of their employees and reinvent their workforce in an AI world. 

We have strategic partnerships with 150+ Global 2000 companies who rely on our training programs to develop the world's most productive and admired workforces. Now we are building what comes next. 

About the Team

Our Workforce Reinvention team is at the forefront of driving efficiency and innovation across OpenSesame. We operate in an agile, continuously improving environment focused on optimizing workflows and empowering internal teams through practical automation and AI-driven solutions. 

The team partners closely with non-technical business groups including Sales, Marketing, and Finance to build scalable systems that reduce operational toil and accelerate productivity across the enterprise.

About the Role

The Workforce Reinvention – AI Engineer will help scale modular tools, intelligent workflows, and production-grade Retrieval-Augmented Generation (RAG) systems that support internal business operations. This person will serve as a pragmatic builder who consistently selects the most efficient solution for each challenge, whether through system integrations, lightweight scripting, reusable automation components, or custom AI agents.

The role will focus initially on maturing existing AI proofs-of-concept into reliable production systems while establishing engineering rigor through Test-Driven Development (TDD), CI/CD automation, infrastructure-as-code practices, and operational monitoring. 

Success in this role will require strong partnership with internal “AI Champions” across departments to create reusable automation capabilities that empower teams to safely self-serve and scale intelligent workflows across OpenSesame.  

Performance Objectives

30 Days — Onboarding, Context, and First Contribution

• Develop a comprehensive understanding of the current Workforce Reinvention architecture, codebase, deployment pipeline, and existing AI proofs-of-concept while building strong working relationships with AI Champions in Sales, Marketing, and Finance.
• Within the first month, successfully contribute and deploy a small but meaningful workflow improvement, automation script, or enhancement to an active internal tool while demonstrating the ability to operate within the team’s TDD and CI/CD practices and release processes.

60 Days — Production Launch & Component Foundations

• Take ownership of deploying a production-grade RAG workflow or intelligent internal tool built from a previously validated concept, ensuring the solution is stable, maintainable, and valuable to internal stakeholders. 
• Partner closely with AI Champions to identify and prioritize workflow bottlenecks while beginning to establish reusable modular automation blocks and standardized development patterns that form the foundation of a scalable enterprise component library.

90 Days — Engineering Rigor & Pipeline Optimization

• Lead improvements to the CI/CD pipeline that significantly reduce manual deployment steps, improve release reliability, and accelerate software delivery across automation initiatives.
• Begin implementing infrastructure-as-code practices using tools such as Terraform while introducing robust monitoring, logging, and observability standards that improve system reliability, track operational costs, and support a target uptime of 99.9% for critical internal automation APIs and workflows.

6 Months — The Scalable Automation Ecosystem

• Fully establish and maintain a reusable component library that enables rapid deployment of AI-driven and traditional automation workflows across multiple business units while empowering AI Champions to safely self-serve and scale departmental solutions independently. 
• Create a sustainable operational model where engineering maintains stable infrastructure, automated testing eliminates operational toil, documentation supports non-technical users, and intelligent workflows become a dependable force multiplier across the organization.

What Success Looks Like

• Successfully turns experimental AI ideas into scalable production systems that improve operational efficiency across OpenSesame.
• Builds reliable, maintainable automation frameworks that internal teams can confidently use and expand on.
• Becomes a trusted technical partner to AI Champions and helps create a scalable automation ecosystem that increases productivity across the company.

You might notice we don’t list a traditional set of requirements or buzzwords here. That’s intentional.

We’re looking for proven examples from your career that show you can build brands, create scalable systems, and drive measurable marketing impact. When you look back a year from now, you’ll know you’ve elevated OpenSesame’s brand and strengthened its market presence.

Location: This position can be based anywhere in the US. We operate as a remote-first company and invest in all-company in-person meetings several times a year. 

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 salary for this role range between $150,000 - $170,000  per year, 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. We carefully consider a wide range of compensation factors, relying on market data to determine compensation and consider your specific job family, background, skills, and experience. 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.

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.

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