Technical Enablement Director
Confirmed on the employer's own hiring board on Oct 17, 2026. First seen by Alion on Jan 30, 2026. Sentry scores A on the Alion truth index.
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 looking for a talented Technical Enablement Director to help drive usage and adoption of our platform through education and enablement. This position will be responsible for strategy, planning, and end-to-end execution of training and educational programs, both internal for our employees, and external for our customers and partners.
You are part product evangelist, part multimedia content producer, part teacher who loves to inspire and educate customers. You are a dynamic, thoughtful, creative professional who can translate technology with compelling stories, and uses analytical skills to drive continuous improvement.
You will partner closely with cross-functional stakeholders including Marketing, Product, Engineering, and Design. This is a uniquely strategic and operational role with a mix of 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. If you’re a technologist with experience working with technical products in customer-facing roles-and you’re eager to join a fast-growing team delivering real value through an exceptional product-we’d love to meet you.
In this role you will:
Become a Sentry product expert: be intimately familiar all product capabilities, and how how customers are using the product
Own the Sentry University virtual learning platform: prepare the curriculum, build the different learning units, create the content, and manage the overall user experience
Create a comprehensive training strategy to enable our customers to quickly ramp on our platform, and accelerate their TTV
Build out and operationalize an engaging certification program for customers, partners, and employees.
Design and own all end-user training content that will be used by CSMs and SEs to deliver to our customers and prospects
Create and deliver an instructor-led training curriculum that would inspire customers to use our product, through virtual group training, and in-person workshops (when it’s safe to travel!)
Work in close partnership with sales and marketing to track progress of leads within the Sentry University
Collaborate with Product and Engineering to ensure the enablement materials are always up to date, continuously update as needed, and meet standards of company branding, messaging and design.
Develop programs and training materials to drive the onboarding and ongoing technical enablement of our technical customer facing teams for topics related to our space (logging, monitoring, cloud, etc).
Develop KPIs that measure adoption and effectiveness of the training programs.
You’ll love this job if you:
Enjoy talking about technology and interfacing with engineers and engineering leaders
Are looking to make an impact in the life of our customers through teaching them how use our product to achieve their business and technical goals
Appreciate working on a variety of projects with different stakeholders
Like being “in the middle of it all”, working across the organization to move the product forward
Have a fast-paced, results-driven mindset
Love developer tools, open-source, and/or all things software development life cycle
Qualifications
Strong knowledge in the application monitoring field
5+ year experience in technical training development and delivery
BA/BS degree in CS or Computer Engineering-related field or equivalent experience is mandatory
Strong verbal and written communications skills with an ability to build rapport and credibility with technical and business audiences
Strong presentation skills
Significant experience working with customers and partners, both remotely and in person
Ability to think out of the box to develop structured training plans, actions, and measurable metrics
Experience leveraging various learning tools and media to provide optimal learning
Equal Opportunity at Sentry
Sentry is committed to providing equal employment opportunities to its employees and candidates for employment regardless of race, color, ancestry, religion, sex, national origin, sexual orientation, age, citizenship, marital status, disability, gender identity, veteran status, or other legally-protected characteristic. This commitment includes the provision of reasonable accommodations to employees and candidates for employment with physical or mental disabilities who require such accommodations in order to (a) perform the essential functions of their jobs, or (b) seek employment with Sentry. We strive to build a diverse team, with an inclusive culture where every teammate can thrive. Sentry is an open-source company because we believe that everyone, everywhere, should have the ability and tools to make great software. Software should be accessible. That starts with making our industry accessible.
If you need assistance or an accommodation due to a disability, you may contact us at [email protected].
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