Engineering Manager, Machine Learning

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 100,000+ organizations, Sentry is today’s application monitoring standard and our team is building its AI-native future. About the role AI and machine learning are reshaping how developers debug, monitor, and ship software, and Sentry is uniquely positioned to lead that shift. We sit on a novel and massive dataset of real production errors, spans, and logs from tens of thousands of engineering organizations — the kind of signal that makes ML genuinely useful, whether it's a clustering model that groups related issues, a ranking system that surfaces the right alert at the right time, or an agent that proposes a fix. We're looking for an Engineering Manager to lead and grow our Machine Learning Engineering team. This team owns the full spectrum of ML at Sentry: classical techniques like clustering, ranking, anomaly detection, and embeddings that quietly power core product surfaces today, alongside the LLM-based and agentic systems shaping where the product is headed. You'll partner closely with product, design, and engineering leaders to decide where ML belongs in our products, what kind of ML actually fits the problem, and how we translate that work into experiences millions of developers rely on every day. In this role you will Set technical direction across the team's full ML surface area — from classical models for clustering, ranking, and anomaly detection to LLM-based and agentic systems — and make sharp calls about which approach fits each problem Define how the team evaluates and monitors ML systems in production, from offline metrics to online experimentation to model and agent observability Stay hands-on enough to review code and model designs, contribute to architecture discussions, and unblock engineers on complex ML problems Define team roadmap and deliverables, scope work, allocate resources, and keep execution on track against ambitious goals Partner with product managers, designers, and engineering leaders across Sentry to identify the highest-impact opportunities for ML in our products Foster career growth for the engineers on your team, and recruit exceptional ML talent as the team scales You'll love this role if you Have a strong ML engineering background that you use to inform and validate the team's technical decisions, and you're comfortable staying close to the code Are excited to shape how AI and developer tools come together, and want to define how engineers and coding agents collaborate to find and fix problems Are driven by impact and want to lead a team working on high-stakes, high-visibility projects Love building things from the ground up — the ML team is still in its early chapters, and there's plenty of greenfield to shape Thrive in cross-functional environments and enjoy collaborating across product, design, and engineering to ship great work Care deeply about growing the engineers around you and finding opportunities for them to do the best work of their careers Qualifications 8+ years of professional engineering experience, with significant time spent building and shipping machine learning systems in production 3+ years of engineering management experience, ideally leading ML, AI, or data-focused teams Familiarity with deploying and operating ML models at scale, including evaluation, monitoring, and iteration in production Strong judgment in ambiguous, fast-moving environments Excellent written and verbal communication; comfortable working across product, research, and engineering A research background in machine learning, statistics, or a related field (MS, PhD, or equivalent research experience) is a plus but not a requirement Not sure if you meet 100% of the qualifications? We encourage you to apply anyway. We're interested in people who are excited about this opportunity and eager to grow. The base salary range (or hourly wage range, if applicable) that Sentry reasonably expects to pay for this position is $220,000 to $280,000. A successful candidate's actual base salary (or hourly wage) amount will be determined by a variety of relevant factors including, without limitation, the candidate's work location, education, work and other relevant experience, skills, and job-related knowledge. A successful candidate will be eligible to participate in Sentry's employee benefit plans/programs applicable to the candidate's position (including incentive compensation, equity grants, paid time off, and group health insurance coverage). See Sentry Benefits for more details about the Company's benefit plans/programs. 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. 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