Technical Enablement Director

About Sentry

Bad software is everywhere, and we’re tired of it. Sentry is on a mission to help developers write better software faster so we can get back to enjoying technology.

With more than $217 million in funding and 100,000+ organizations that believe we’re on to something, we're building performance and error monitoring tools that help companies like Disney, Microsoft, and Atlassian spend less time fixing bugs and more time building products.

Sentry embraces a hybrid work model across our global hubs, with Mondays, Tuesdays, and Thursdays set as in-office anchor days to encourage meaningful collaboration. If you like to selfishly build things that make your digital life better, come help us build the next generation of software monitoring tools.

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].

Want to learn more about how Sentry handles applicant data? Get the details in our Applicant Privacy Policy.