Manager of AI Data Operations

OpenSesame’s mission is to help develop the world’s most productive and admired workforces. We do this by delivering a comprehensive catalog of elearning courses from the world’s top publishers. We add value to customers through their entire learning journey.

While it appears to most people that we just sell training courses (over 20,000 of them), what we really offer is the opportunity for companies to upgrade the skills of each of their employees.

We are at a pivotal time in our growth as we diversify the ways we drive revenue. We’ve expanded our product offering dramatically, and have a growing network of partners that is developing into a vibrant channel. Our customer base has high satisfaction ratings and there is room to grow our retention even more.

About the Job:

The Manager of Data and Generative AI Operations plays a pivotal role at OpenSesame, a leader in e-learning solutions. This role is responsible for overseeing the operational management and strategic deployment of data analysis and generative AI technologies to enhance the company’s product offerings and operational efficiency. The Manager will lead initiatives to leverage data-driven decision-making and implement cutting-edge AI tools to propel OpenSesame towards its mission of developing the world’s most productive and admired workforces.

Performance Objectives:

In your first 90 days, you will be ramping up and working to understand the needs and opportunities of the analytics team as well as forming a plan for rollout of analytics and GAI tools company-wide. You will develop this plan in collaboration with management and begin executing that plan with your team.


  • Establish strong relationships with your team as well as internal stakeholders to understand their needs and how data and AI can support their objectives.


  • Lead cross-departmental collaboration to ensure alignment of data and AI initiatives with broader organizational goals.


  • Level up the data platform to include all data sources necessary for the department champions to build custom GPTs without having to worry if their data is available.

Within 6 months, your GAI efforts will be well-underway with multiple productivity enhancements implemented and delivering significant business value. You will have established yourself as a trusted expert within the company. You will have made connections with stakeholders across the organization.


  • Establish a culture of continuous learning and innovation within the team, fostering an environment where experimentation and calculated risks are encouraged.


  • By the end of the first six months, implement key performance indicators (KPIs) and regular reporting mechanisms to measure the effectiveness of data and AI operations.


  • Deploy the first round of department-wide GAI-backed efficiency solutions

By the end of your first year, you will have contributed to a massive increase in efficiency across the company. Your team will have transitioned from taking tickets to enabling better decision-making and strategy across the entire company.


  • You’ve successfully upskilled and inspired your team to contribute to company-wide efforts to improve efficiency and quality of data products


  • Continuously review and improve operational processes to increase efficiency, reduce costs, and improve data quality.


  • Continue to regularly release new GenAI and analytics products.Regularly present insights and progress reports to executive leadership, demonstrating the impact of data and AI initiatives on the organization’s strategic goals.
  • The company as a whole has improved efficiency through the efforts of you and your team.

Tech Stack: OpenSesame’s tech stack is too expansive to list here but includes our own industry-leading SaaS products in the adult education industry as well as hundreds of best-in-class vendors powering our business operations. You’ll have the opportunity to use cutting-edge tools and guid the future tech stack in analytics and Generative AI

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 pay for this position depends on experience and generally ranges between $130,000.00-160,000.00 annually. 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. 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 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.

💰$130,000 - $160,000/Yearly

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