Senior Software Engineer, AI

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 As a Senior Software Engineer on Sentry’s AI/ML team, you’ll be responsible for building the evaluation infrastructure that measures the accuracy, reliability, and real-world performance of our AI systems. This role is critical to ensuring that our debugging agents and AI-powered features behave correctly, safely, and predictably as they scale. You’ll design datasets, benchmarks, and test harnesses that turn ambiguous AI behavior into measurable signals, helping the team ship AI with confidence. In this role you will Design and build robust evaluation frameworks to measure accuracy, reliability, regressions, and edge cases in AI systems Create and curate high-quality datasets, golden test cases, and benchmarks grounded in real production data Build automated test harnesses and metrics pipelines to continuously evaluate models, prompts, and agentic workflows Partner closely with applied AI engineers and product leaders to define what “good” looks like and translate it into measurable criteria Own the evaluation lifecycle for major AI initiatives, from early experimentation through production monitoring You’ll love this job if you Care deeply about correctness, rigor, and measurement in AI systems Enjoy turning fuzzy product goals and model behavior into concrete tests and metrics Like building foundational infrastructure that unlocks faster iteration and higher confidence for the entire AI team Thrive in cross-functional environments and enjoy influencing model design through better evaluation Qualifications Minimum 5+ years of professional experience with a Bachelor’s degree in computer science, machine learni

We believe that the way people interact with their finances will drastically improve in the next few years. We’re dedicated to empowering this transformation by building the tools and experiences that thousands of developers use to create their own products. Plaid powers the tools millions of people rely on to live a healthier financial life. We work with thousands of companies like Venmo, SoFi, several of the Fortune 500, and many of the largest banks to make it easy for people to connect their financial accounts to the apps and services they want to use. Plaid’s network covers 12,000 financial institutions across the US, Canada, UK and Europe. Founded in 2013, the company is headquartered in San Francisco with offices in New York, Washington D.C., London and Amsterdam. Team: Plaid is becoming an AI-first company, and Intelligent Tooling builds internal platforms and tools to lead the transformation. Our biggest opportunity isn't just better tools for engineers, it's extending AI-native internal tooling to the rest of Plaid. Tools built for engineers assume things non-engineers don't have: local toolchains, monorepos, engineer credentials, PR-based workflows. That mismatch means Ops, Support, and other teams can't easily inherit what we build for engineering. They need their own path and we're building that path. Role: As a Senior Software Engineer on Intelligent Tooling, you will build and operate internal systems that empower non engineering teams to automate their workflows with AI. You will own the product and platform layer for internal tools, including the constraints and infrastructure that keep those tools safe and maintainable. There's no existing playbook for this at Plaid. You will define what the right non-eng AI surface looks like, ship its first durable versions, and partner closely with internal users to make sure it solves real problems. You will act as the engineering point of contact embedded with non-engineering teams, running discovery and trans

Secure Every Identity, from AI to Human Identity is the key to unlocking the potential of AI. Okta secures AI by building the trusted, neutral infrastructure that enables organizations to safely embrace this new era. This work requires a relentless drive to solve complex challenges with real-world stakes. We are looking for builders and owners who operate with speed and urgency and execute with excellence. This is an opportunity to do career-defining work. We're all in on this mission. If you are too, let's talk. Okta is the identity standard. The Okta Platform is an independent and neutral platform that securely connects the right people to the right technologies at the right time. We help organizations do two things - secure and manage their extended enterprise, and transform their users’ experiences. Okta's Core Engineering team is responsible for building and evolving shared infrastructure and services that lay the foundation for what other engineering teams build on. We're in charge of common shared services like search, cache, configuration management, frameworks for async job management, and email pipeline, to name a few. We're cloud native, where redundancy, multi-tenancy, scale, resource optimization and resiliency are first class citizens. With Okta's mantra of 'Always On!' there's never a dull moment. Our biggest asset is our team of passionate engineers and technically minded managers. We're looking for a staff level backend engineer to join a team of highly skilled and talented team players who're proud of what they own and deliver. Our elite team is fast, creative and flexible; with a weekly release cycle and individual ownership we expect great things from our engineers and reward them with stimulating new projects, new technologies and the chance to have significant equity in a company that is changing the cloud computing landscape forever. You will: Work with engineering teams to design, develop and deliver cloud based infrastructu

Why join us Brex is the intelligent finance platform that enables companies to spend smarter and move faster in more than 200 markets. By combining global corporate cards and banking with intuitive spend management, bill pay, and travel software, Brex enables founders and finance teams to accelerate operations, gain real-time visibility, and control spend effortlessly. Brex’s AI-native automation and world-class service eliminate manual expense and accounting tasks for customers so they can focus on what matters most. Tens of thousands of the world's best companies run on Brex, including DoorDash, Coinbase, Robinhood, Zoom, Plaid, Reddit, and SeatGeek. Working at Brex allows you to push your limits, challenge the status quo, and collaborate with some of the brightest minds in the industry. We’re committed to building a diverse team and inclusive culture and believe your potential should only be limited by how big you can dream. We make this a reality by empowering you with the tools, resources, and support you need to grow your career. Data at Brex Our Scientists and Engineers work together to make data — and insights derived from data — a core asset across Brex. But it’s more than just crunching numbers. The Data team at Brex develops infrastructure, statistical models, and products using financial data. Our work is ingrained in Brex’s decision-making process, the efficiency of our operations, our risk management policies, and the unparalleled experience we provide our consumers. What you’ll do This position is on our Data Enablement Platform team. The Brex product requires a huge amount of data to power our client experiences. With a largely async architecture, proliferation of services and multiple operations systems, this data originates from many different sources and in different forms. To ensure that our product experience is unbounded in how it leverages this data, the Data Enablement Platform team owns and operates the systems required to deliver it t

About Flexport: At Flexport, we believe global trade can move the human race forward. That’s why it’s our mission to make global commerce so easy there will be more of it. We’re shaping the future of a $10T industry with solutions powered by innovative technology and exceptional people. Today, companies of all sizes—from emerging brands to Fortune 500s—use Flexport technology to move more than $19B of merchandise across 112 countries a year. The recent global supply chain crisis has put Flexport center stage as we continue to play a pivotal role in how goods move around the world. We are proud to have the support of the best investors in the game who believe in our mission, solutions and people. Ready to tackle global challenges that impact business, society, and the environment? Come join us. The Opportunity The Autonomous Freight Systems team is a brand new, AI-first engineering team in San Francisco, building Flexport's client-facing rates platform and self-serve freight booking experience from the ground up. We own two of the highest-leverage surfaces in the Client App: how clients see pricing and how they book freight without manual intervention. As a Senior Engineer, you will own significant technical domains end-to-end, not just features, but whole problem spaces. You will drive the engineering of systems that power rate visibility, pricing intelligence, and AI-assisted booking across ocean, air, and trucking. You don't wait to be told what to build next; you identify the highest-leverage problems, propose solutions, and see them through to production. You will be a technical force multiplier on the team: raising the bar on code quality, helping junior engineers grow, and shipping with a velocity and confidence that comes from deep ownership. This is a ground-floor opportunity to build the platform that moves Flexport from an assisted-sales model to a tech-run one for the long tail of our client base—turning the complexity of global trade into a s

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 team The Billing team sits at the intersection of product, finance, and infrastructure. They're responsible for ensuring every observable event—errors, logs, traces, tokens—gets accurately measured, priced, and billed. Their work directly impacts company revenue and customer trust, requiring distributed systems expertise, attention to financial accuracy, and deep understanding of product usage patterns. The team works cross-functionally with product, engineering, BizOps, marketing, and sales to build systems that enable new products and pricing models. About the role As a Senior Software Engineer, you will architect and scale the core systems that power Sentry's billing infrastructure, ensuring accuracy and reliability at massive scale. You will collaborate on building the next generation of Sentry’s usage tracking pipeline, processing hundreds of billions of events daily with low latency and financial-grade accuracy. You will help design flexible pricing primitives that support everything from per-event usage billing to complex enterprise contracts, enabling product and sales teams to experiment rapidly while maintaining revenue accuracy and reduced time-to-market for new products. You will contribute to technical decisions on data consistency challenges unique to billing—like handling event delays, retroactive pricing changes, and distributed count reconciliation across our infrastructure. You'll love this job if you Want to solve the "easy to explain, hard to build" problems—like ensuring a customer's bill matches their usage perfectly, even when processing hundreds of billions of events daily across distributed