---
title: 'Technical Enablement Director at Sentry'
canonical: 'https://feeny.ai/job/technical-enablement-director-sentry-san-francisco-rvn7817a3hxk'
type: 'job'
last_seen: '2026-09-04'
---

# Technical Enablement Director at Sentry

- **Company:** Sentry
- **Location:** San Francisco, CA
- **Employment:** full-time
- **Work type:** hybrid
- **Posted:** 2026-08-28
- **Last confirmed live:** 2026-09-04
- **Apply:** https://jobs.ashbyhq.com/sentry/ee7542d4-f478-4aa0-8da9-3583845d8269

## 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 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 accommodations@sentry.io.

Want to learn more about how Sentry handles applicant data? Get the details in our Applicant Privacy Policy https://sentry.io/careers/applicantprivacy/.

## About Sentry

## Company Overview
- **One-liner**: Sentry is the leading application performance monitoring and error-tracking platform that helps developers diagnose, fix, and optimize code in real-time.
- **Entity Type**: Private (Series E)
- **Headquarters**: San Francisco, California, USA
- **Founded**: 2012
- **Founders**: David Cramer, Chris Jennings

## Core Business
- **Primary industry**: Application Performance Monitoring (APM) and Error Tracking Software
- **Target customers**: B2B; developers and engineering teams at organizations of all sizes, from startups to large enterprises (200K+ organizations)
- **Mission or purpose**: To give every developer the tools to build better software, faster, by making debugging and performance monitoring accessible and indispensable.

## Products & Services
- **Sentry Error Tracking**: The core product — real-time error monitoring that captures, aggregates, and surfaces software bugs across 100+ coding languages and frameworks. [sentry.io](https://sentry.io/welcome/)
- **Sentry Performance Monitoring**: Traces slow transactions, API calls, and database queries to help developers optimize application speed and reliability. [sentry.io](https://sentry.io/welcome/)
- **Sentry Session Replay**: Video-like replays of user sessions to see exactly what happened before, during, and after an error. [sentry.io](https://sentry.io/welcome/)
- **Sentry Profiling**: Continuous code profiling to identify performance bottlenecks at the function level. [sentry.io](https://sentry.io/welcome/)
- **Sentry Crash Reporting (Cocoa/Android)**: Native SDKs for mobile error tracking and performance monitoring. [sentry.io](https://sentry.io/welcome/)
- **Seer (AI Debugging Agent)**: An AI-powered tool that uses Sentry context (logs, commits, traces) to automatically root-cause issues and generate merge-ready patches. [sentry.io](https://sentry.io/welcome/)
- **Sentry MCP Server**: Integrates with coding agents to bring full debugging context directly into the developer's workflow. [sentry.io](https://sentry.io/welcome/)

## Market Standing
- **Valuation/Market Cap**: Not publicly disclosed (last known funding round was $217M total raised)
- **Key Metric**: $217M total funding raised across 6 rounds; processes 190B+ events daily; serves 200K+ customers and 4M+ total users across 146 countries [sentry.io](https://sentry.io/about/)
- **Notable Investors/Partners**: Backed by prominent venture capital firms (specific names not listed on the about page, but the company has raised significant capital). Key integrations include GitHub, Slack, Jira, and Linear. [sentry.io](https://sentry.io/welcome/)
- **Growth Signals**: Acquired Codecov in December 2022 to expand into code coverage; processes 790B+ events per month; has 200+ employees across offices in San Francisco, Vienna, Toronto, Amsterdam, New York, and Sydney. [sentry.io](https://sentry.io/about/)

## Competitive Advantages
- **Developer-First DNA**: Built by developers for developers, with an open-source heritage that fosters deep trust and community adoption.
- **Unified Observability Platform**: Uniquely connects errors, logs, session replays, traces, profiles, and metrics under a single trace ID, providing end-to-end context that competitors like Datadog or New Relic offer as separate products.
- **AI-Native Debugging**: Seer, the AI debugger, goes beyond simple alerting to automatically root-cause issues and generate patches, a significant moat in the AI-assisted development space.
- **Massive Scale & Community**: Loved by millions of developers and 200K organizations, with 190B+ events processed daily, creating a powerful network effect and data advantage for AI models. [sentry.io](https://sentry.io/about/)

## Strategic Focus
- **AI-Powered Developer Tools**: Deep investment in AI (Seer, AI code review, AI evals) to move from passive monitoring to proactive debugging and automated fixing.
- **Unified Observability**: Continuing to break down silos between errors, performance, logs, and replays into a single, trace-connected experience.
- **Platform Expansion**: Growing beyond error tracking into a full-stack observability and developer productivity platform, including code coverage (via Codecov acquisition) and AI-assisted development.
- **Enterprise Scale**: Building out capabilities for large organizations (enterprise product marketing, solutions engineering, security compliance) while maintaining a strong developer experience.

## Why Work Here
- **Culture & Values**: Emphasizes "pixels matter" (attention to detail), constructive feedback, iteration, and valuing people from diverse backgrounds. The culture is described as relatively small, fast-growing, and highly influential. [sentry.io](https://sentry.io/careers/)
- **Remote/Hybrid Policy**: Offers roles across multiple global offices (San Francisco, Toronto, Vienna, Amsterdam, New York, Sydney) with a mix of in-office and remote positions. The careers page lists specific locations for each role. [sentry.io](https://sentry.io/careers/)
- **Notable Perks**: Competitive compensation + equity, flexible PTO, paid parental leave, medical/dental/vision insurance, 401k plan (US), commuter benefits, professional development stipend, charitable matching program, and a well-stocked office (including "a minimum of six different brands of sparkling water"). [sentry.io](https://sentry.io/careers/)
- **Engineering Culture**: High ownership and autonomy; engineers influence product, brand, and culture. The company is known for shipping high-quality code and has a strong open-source ethos. [sentry.io](https://sentry.io/careers/)
- **Diversity & Inclusion**: Committed to equal employment opportunity and providing reasonable accommodations. Explicitly states that software should be accessible, starting with making the industry accessible. [sentry.io](https://sentry.io/careers/)

## Sources
1. [sentry.io](https://sentry.io/about/)
2. [sentry.io](https://sentry.io/careers/)
3. [sentry.io](https://sentry.io/welcome/)
4. [jobs.ashbyhq.com](https://jobs.ashbyhq.com/sentry)
5. [greatplacetowork.com](https://www.greatplacetowork.com/certified-company/7024898)

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