Technical Enablement Director

About SentrySoftware 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...