Technical Enablement Director

Details

About Sentry

Bad software is everywhere, and Sentry is on a mission to help developers write better software faster. Sentry builds performance and error monitoring tools used by organizations such as Disney, Microsoft, and Atlassian.

Sentry embraces a hybrid work model across its global hubs, with Mondays, Tuesdays, and Thursdays set as in-office anchor days to encourage meaningful collaboration.

Role overview

Sentry is looking for a Technical Enablement Director to drive usage and adoption of the Sentry platform through education and enablement. The role combines product evangelism, multimedia content production, and teaching to translate technology into compelling stories and measurable learning outcomes. This position partners closely with Marketing, Product, Engineering, Design, Sales, and Customer Success and has both internal and external responsibilities.

This role requires strong technical expertise and a deep understanding of the Software Development Life Cycle (SDLC) and related technologies. Responsibilities include strategy, planning, and end-to-end execution of training and educational programs for employees, customers, and partners.

Responsibilities

• Become a Sentry product expert and understand product capabilities and customer usage patterns.
• Own the Sentry University virtual learning platform: prepare curriculum, build learning units, create content, and manage user experience.
• Create a comprehensive training strategy to enable customers to ramp on the platform quickly and accelerate time-to-value (TTV).
• Build and operationalize a certification program for customers, partners, and employees.
• Design and own end-user training content used by Customer Success Managers (CSMs) and Sales Engineers (SEs).
• Create and deliver instructor-led training: virtual group training and in-person workshops (when travel is appropriate).
• Work with Sales and Marketing to track progress of leads within the Sentry University.
• Collaborate with Product and Engineering to keep enablement materials up to date and aligned with company branding, messaging, and design.
• Develop programs and training materials for onboarding and ongoing technical enablement of customer-facing teams on topics related to the space (logging, monitoring, cloud, etc.).
• Develop KPIs that measure adoption and effectiveness of training programs.

Requirements / Qualifications

• Strong knowledge in the application monitoring field.
• 5+ years of experience in technical training development and delivery.
• BA/BS degree in Computer Science or Computer Engineering (or equivalent experience) is mandatory.
• Strong verbal and written communications skills; ability to build rapport and credibility with technical and business audiences.
• Strong presentation skills and significant experience working with customers and partners, both remotely and in person.
• Ability to develop structured training plans, measurable metrics, and think creatively about enablement programs.
• Experience leveraging various learning tools and media to provide optimal learning experiences.
• Deep understanding of the Software Development Life Cycle (SDLC) and related technologies; familiarity with logging, monitoring, and cloud technologies.

You’ll love this job if you:

• Enjoy talking about technology and interfacing with engineers and engineering leaders.
• Want to impact customers through teaching them to use the product to achieve business and technical goals.
• Appreciate working on a variety of projects with different stakeholders and being "in the middle of it all."
• Have a fast-paced, results-driven mindset and like developer tools, open-source, and software development lifecycle topics.

Benefits

• Not specified in the job listing.

Location & Work Model

• Location: San Francisco, California (Hybrid). Mondays, Tuesdays, and Thursdays are in-office anchor days.

Equal Opportunity

Sentry is committed to equal employment opportunities and provides reasonable accommodations for candidates with disabilities. For accommodation requests, contact [email protected].