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.

Learn more: www.opensesame.com/about

About the Team:

The Customer Success Operations team enables the Customer Success organization to work smarter, scale more effectively, and deliver better customer outcomes. This team partners across systems, process design, lifecycle strategy, and automation to improve how we support customers across both managed and digitally led motions.

About the Role:

OpenSesame is hiring a data-driven, systems-minded, and highly analytical CS Operations Analyst to help power smarter decision-making across the Customer Success organization. This role will own the reporting, dashboards, and data-informed automation support for Customer Success teams.

As an operator on this team, you will turn customer and operational data into reliable dashboards, clear and actionable insights, and scalable automations. You will be the bridge between our data and our strategy - working alongside Data Engineering to ensure we have the right data foundations, and partnering with the CS Ops Manager to turn those foundations into scalable automation solutions, including scorecards, lifecycle programs, and tech touch strategies.

This operator will help shape the future of Customer Success at OpenSesame by designing human+AI workflows that expand CSM capacity, improve consistency, and better service our customers across segments.

What you'll do:

• Build and own scalable reporting, dashboards, and forecasting that give CSM and Customer Success leaders clear visibility into customer health, risk, and growth opportunities.
• You will act as a steward for CS data integrity, collaborating with Data Engineering to establish the standards and definitions that ensure our metrics are consistent and trusted across the company.
• Turn customer, product, and revenue data into actionable insights that drive retention, expansion, and smarter lifecycle decisions.
• Partner cross-functionally to translate insights into action—shaping health scores, segmentation, automations, and customer programs.
• Leverage AI and automation tools to scale customer outreach, predict churn risks, and reduce manual operational overhead for the CS team.
• Design and implement AI-powered and agent-based workflows that help CSMs manage their portfolios more efficiently and spend more time on strategic customer work.

Key Performance Objectives:

Within 30 days:

• Build a strong understanding of OpenSesame's Customer Success strategy, customer motions, lifecycle stages, KPIs, and operating rhythms.
• Learn the current reporting environment, dashboard landscape, data sources, and definitions used across Customer Success.
• Build relationships with CS leadership, CS Ops, and key cross-functional partners.
• Identify early opportunities to improve data quality, reporting clarity, and dashboard usability.

Within 60 days:

• Take ownership of core CS dashboards and recurring reporting.
• Partner with CS Ops to identify automation opportunities backed by data and operational needs.
• Improve confidence in core CS reporting by resolving inconsistencies, clarifying logic, or simplifying access.
• Deliver initial analyses on customer health, segment performance, lifecycle friction points, or tech-touch opportunities.
• Identify repeatable CSM tasks that can be delegated to automation or agents.

Within 90 days:

• Launch or significantly improve a core suite of Customer Success dashboards used by leadership and frontline teams.
• Provide reporting and analysis that improves early risk detection, visibility into expansion opportunities, and renewal forecast accuracy.
• Establish a repeatable rhythm for delivering insights that influence prioritization, planning, and program design.
• Present at least 1–2 data-backed recommendations that lead to operational improvements, lifecycle changes, or new automation efforts.
• Become a trusted partner to CS leadership and CS Ops in using data to improve team performance and customer outcomes.

Within 6-12 months, you will:

• Be the go-to partner for Customer Success reporting, analysis, and data storytelling.
• Build scalable foundations across data, automation, and workflow design that make AI adoption and lifecycle optimization easier to implement across Customer Success.
• Build or orchestrate agent-based solutions with clear guardrails.

Success in this role looks like:

• Customer Success has a single trusted owner for dashboards, reporting, and analysis.
• Leadership decisions are faster, more confident, and grounded in reliable data.
• CS Ops can operationalize better automations and lifecycle programs because the underlying analysis is stronger.
• CSMs get clearer visibility into risk, opportunity, and next-best action.
• Managed and digitally led motions improve because data is actively shaping where we invest.
• Our CS Teams operate within the human+AI framework through the automations, AI tools, and agent-based workflows.

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: On-target earnings for this role range between $110,000 and $120,000 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.

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 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