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Salary: USD 160,000 - 180,000 / annual
Sentry is an application monitoring platform trusted by 200,000+ organizations. The company helps developers fix errors and performance issues before users notice them, enabling teams to spend less time firefighting and more time building.
You will lead Sentry's Support Engineering team as a hands-on manager. This role combines people leadership, strategic support operations, and direct customer engagement. You'll manage and coach a team of Technical Support Engineers, set clear expectations for technical depth and response quality, and design coverage models across time zones including on-call and escalation paths. You'll build career development paths for engineers who want to deepen technically, move into management, or transition to other teams.
On the outcomes side, you'll own core support metrics including customer experience, time to resolution, and escalation rates. You'll use support conversations as a signal to identify top drivers of tickets and work to fix them at the source—whether in the product, documentation, internal operations, or SDKs—rather than just answering faster.
A significant part of this role involves owning the roadmap for AI-assisted support. You'll decide which request types AI agents handle, what context they need, and when they hand off to humans. You'll set quality bars for agent answers and build processes to catch incomplete responses. You'll use data to determine where automation is worth building and where it isn't.
You'll also handle escalations and partner across Sentry. You'll run the escalation process with Engineering to ensure bugs reach the right team with clear reproductions and impact statements. You'll lead on high-stakes enterprise issues, working with Customer Success, Solutions Engineering, and Sales. You'll bring a clear, data-backed picture of customer pain to Product and Engineering.
This is ideal if you think great support is an engineering problem, not a staffing problem; want to build teams and systems simultaneously; can debug tricky SDK issues yourself while explaining incidents to executives; prefer fixing the root cause of 200 tickets over answering them faster; and have strong, evidence-based opinions on where AI helps in support and where it creates problems.
REQUIREMENTS:
- 8+ years in technical support, support engineering, or software engineering at a SaaS or developer tools company
- 3+ years managing technical support engineers, including hiring and growing a team
- Technical credibility with senior engineers: comfortable reading code in Python, JavaScript/TypeScript, Java, or Ruby, and debugging across frontend, backend, and infrastructure
- Solid understanding of distributed systems, APIs, and how observability tools (errors, tracing, logs) fit into them
- Hands-on experience running AI or automation in a support organization, with clear understanding of failure modes
- Track record of using support data to drive product and process changes
- Clear, direct written communication with customers, executives, and engineers
BONUS:
- Experience at a developer tools or observability company
- Former software engineer background
- Managed a team spread across multiple time zones
- Open source contributor or maintainer
