About the Role The AI Deployment Manager (ADM) - Pilots is a customer-facing role responsible for leading structured, time-bound enterprise AI pilots from initial scoping through final executive readout. This role is focused on helping customers evaluate OpenAI’s products in real-world contexts, identify high-value use cases, and generate clear, decision-ready signals tied to business value. You will design and lead pilot engagements that drive activation, sustained usage, and measurable impact across ChatGPT Enterprise, Codex, and adjacent workflows. This includes partnering with customer stakeholders to define success criteria, guiding users from experimentation to real adoption, and translating pilot outcomes into clear recommendations that support expansion or purchase decisions. This role requires strong judgment, the ability to operate in ambiguity, and a consistent focus on connecting technical capabilities to business outcomes. You will regularly engage both executive stakeholders and working teams, adapting your approach to meet customers where they are and move them forward. In this role, you will: Own the design and execution of enterprise AI pilots, including scoping, cohort definition, and success criteria aligned to a clear commercial decision. Identify and prioritize a small set of high-impact use cases that can generate credible signal within a 30–45 day pilot. Drive activation and sustained engagement across pilot cohorts through targeted enablement, office hours, and workflow-level coaching. Monitor pilot performance and adapt in real time, diagnosing gaps in engagement, use case traction, or stakeholder alignment. Translate pilot signals into clear, executive-ready recommendations, including whether and how the customer should expand. Navigate customer constraints such as security, data access, and competing tools while maintaining pilot momentum. Partner closely with ADs, SEs, and customer stakeholders to align on scope, risks, and next steps. Ca
Senior Technical Customer Success Manager
Market pay estimate
$87,100–$114,000 / year for comparable Customer Success Manager roles in United States. Not employer-provided.
Role overview
Job description
About Sentry Software runs the world and the pace is faster than ever. Sentry helps developers fix errors and performance issues before users notice, so teams can spend less time firefighting and more time building. Trusted by 200,000+ organizations, Sentry is today’s application monitoring standard and our team is building its AI-native future. About the role: Sentry is expanding our Technical Customer Success team to support our growing customer base and drive deeper adoption of the Sentry Platform worldwide. As a Technical Customer Success Manager (TCSM), you’ll be a Sentry product expert responsible for ensuring customers are successfully onboarded, achieve maximum value from our platform, and uncover new opportunities for growth through additional use cases and products. You’ll play a key role in helping customers realize measurable outcomes with Sentry. In this highly cross-functio
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How Customer Success Manager demand looks in United States
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33
Posted 30d
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Salary listed
48.5%
Salary trend 1Y
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What they are looking for
Skills & requirements
Qualification
This is a technical role combined with business skills. You have to have strong technical background to be successful in this role BA/BS degree in CS or Computer Engineering-related field or equivalent experience is mandatory 5+ years of experience in Customer Success, Account Management, Management Consulting, or another customer-facing role Strong industry experience and technical understanding related to Devs, DevOps, application monitoring, software release tools, and/or broader cloud-native application infrastructure platforms Experience in working with complex, multi-divisional, multi-geographical customers Impressive executive presence and communication abilities Experience working with cross-functional teams (e.g. Sales, Product, Marketing, ProServices) You’re driven; no one needs to push you to excel; it’s just who you are Passion for technology and being a part of a fast-growing SaaS company Bonus qualifications Past experience as a developer/devops Extensive knowledge in application monitoring, Logs, Metrics, Traces Equal Opportunity at Sentry Sentry is committed to providing equal employment opportunities to its employees and candidates for employment regardless of race
Department · Customer Success
Hiring company
Sentry
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