Staff Software Engineer, AI Platform

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 already sees the moment software breaks: the error, the trace, the replay, the commit that caused it. Seer, our AI debugger, uses all of that to figure out what went wrong and how to fix it. We're looking for a Staff engineer to help decide how that system should evolve as models improve every few months. Some of what we build today will be obsolete by next spring. Part of the job is knowing which parts, and building the rest to last. In this role you will Build state-of-the-art agentic AI systems to triage, debug, and solve real production issues Set technical direction for how our agents get context, use tools, and decide when they're done Build the evals that tell us whether a new model or prompt actually helped, fast enough that people use them Decide when to use a frontier model, a smaller one, or one we trained, and revisit that as cost and capability shift Leverage Sentry’s novel (and massive) dataset of errors, spans, and profiles Own major AI initiatives end to end, alongside the developers and product teams shipping them Run what you ship in production and debug it with Sentry You'll love this job if you Are driven by impact and enjoy working on high-stakes, high-visibility projects Enjoy building things. You will have the opportunity to join the AI/ML team as one of its foundational members Thrive in cross-functional teams and enjoy building features alongside developers and product teams Qualifications You've shipped an LLM-backed system people depended on, and can tell us what broke You have strong opinions on agent design and have changed at least one in the last year You've trained or fin

About Decagon Decagon is the leading conversational AI platform empowering every brand to deliver concierge customer experiences. Our technology enables industry-defining enterprises like Avis Budget Group, Block’s Cash App and Square, Chime, Oura Health, and Hunter Douglas to deploy AI agents that power personalized, deeply satisfying interactions across voice, chat, email, SMS, and every other channel. We’re building a future where customer experiences are being redefined from support tickets and hold music to faster resolutions, richer conversations, and deeper relationships. We’re proud to be backed by world-class investors who share that vision, including a16z, Accel, Bain Capital Ventures, Coatue, and Index Ventures, along with many others. We’re an in-office company, driven by a shared commitment to excellence and velocity. Our values — Just Get It Done, Invent What Customers Want, Winner’s Mindset, and The Polymath Principle — shape how we work and grow as a team. About the Team The Agent Platform team builds the runtime and model orchestration layer that powers Decagon’s agents in production. This is the orchestration layer that turns workflows, tools and guardrails into a reliable, low-latency, and delightful experience for end users. At the core of this work is the agent harness: the routing, execution logic, tool orchestration, and control-plane systems that determine how an agent behaves in a live conversation. The team owns the full execution lifecycle of each conversation—from selecting workflows and orchestrating multiple models (e.g., router/planner/supervisor patterns), to coordinating tool calls, enforcing safety constraints, and communicating back to the user. The team operates across both real-time systems (e.g., voice interactions with strict latency requirements) and longer-horizon execution (supporting more complex reasoning and workflows). Our research shows that an agent’s task execution reliability increasingly depends on the orchestration

About Decagon Decagon is the leading conversational AI platform empowering every brand to deliver concierge customer experiences. Our technology enables industry-defining enterprises like Avis Budget Group, Block’s Cash App and Square, Chime, Oura Health, and Hunter Douglas to deploy AI agents that power personalized, deeply satisfying interactions across voice, chat, email, SMS, and every other channel. We’re building a future where customer experiences are being redefined from support tickets and hold music to faster resolutions, richer conversations, and deeper relationships. We’re proud to be backed by world-class investors who share that vision, including a16z, Accel, Bain Capital Ventures, Coatue, and Index Ventures, along with many others. We’re an in-office company, driven by a shared commitment to excellence and velocity. Our values — Just Get It Done, Invent What Customers Want, Winner’s Mindset, and The Polymath Principle — shape how we work and grow as a team. About the Team The Security Engineering team at Decagon protects the platform that powers the most advanced conversational AI agents for enterprise customers across voice, chat, email, and SMS. We build the security foundations that enable Decagon's AI agents to handle sensitive customer data with complete trust while defending against sophisticated, AI-enabled threats at massive scale. This role sits at the intersection of Security and Infrastructure. Like the rest of our Infrastructure org, we believe the best security comes from paved paths, strong SLAs, and high-quality systems that other engineers can rely on by default. Our mission is to secure magical support experiences, ensuring that AI agents and human agents can collaborate safely to help users resolve their issues while maintaining the highest standards of security and privacy. About the Role We're hiring our founding Platform Engineer, Security to design, build, and operate the security infrastructure that powers Decagon's AI platform.

About Decagon Decagon is the leading conversational AI platform empowering every brand to deliver concierge customer experiences. Our technology enables industry-defining enterprises like Avis Budget Group, Block’s Cash App and Square, Chime, Oura Health, and Hunter Douglas to deploy AI agents that power personalized, deeply satisfying interactions across voice, chat, email, SMS, and every other channel. We’re building a future where customer experiences are being redefined from support tickets and hold music to faster resolutions, richer conversations, and deeper relationships. We’re proud to be backed by world-class investors who share that vision, including a16z, Accel, Bain Capital Ventures, Coatue, and Index Ventures, along with many others. We’re an in-office company, driven by a shared commitment to excellence and velocity. Our values — Just Get It Done, Invent What Customers Want, Winner’s Mindset, and The Polymath Principle — shape how we work and grow as a team. About the Team The Voice Agent team builds the real-time systems that allow Decagon agents to carry natural conversations across our omnichannels (phone, web, mobile, etc). We work across speech understanding, audio streaming, synthesis quality, and the voice specific execution logic that enables timing, pacing, and responsive dialogue. Our systems must remain accurate, responsive, and stable at scale. Voice is one of the most technically challenging surfaces in conversational AI, and our small team owns this entire capability end-to-end. About the Role As a Staff Software Engineer focused on Voice Agent, you will lead the architecture and evolution of Decagon’s voice platform. You will drive multi-quarter projects that improve timing, responsiveness, audio quality, and reliability across millions of interactions. You will collaborate with Research to integrate the next generation of speech models, with Infra to push the boundaries of latency and performance, and with Product to bring new voice cap

About Decagon Decagon is the leading conversational AI platform empowering every brand to deliver concierge customer experiences. Our technology enables industry-defining enterprises like Avis Budget Group, Block’s Cash App and Square, Chime, Oura Health, and Hunter Douglas to deploy AI agents that power personalized, deeply satisfying interactions across voice, chat, email, SMS, and every other channel. We’re building a future where customer experiences are being redefined from support tickets and hold music to faster resolutions, richer conversations, and deeper relationships. We’re proud to be backed by world-class investors who share that vision, including a16z, Accel, Bain Capital Ventures, Coatue, and Index Ventures, along with many others. We’re an in-office company, driven by a shared commitment to excellence and velocity. Our values — Just Get It Done, Invent What Customers Want, Winner’s Mindset, and The Polymath Principle — shape how we work and grow as a team. About the Team The Enterprise Product team creates the platform that customers use to build, maintain, and improve their AI agents. We transform complex engineering work into intuitive self-serve products, making sophisticated AI capabilities accessible to both technical and non-technical Customer Experience teams. This team is core to Decagon’s ability to scale: the tools you build directly support agents for all our customers, each with unique workflows, data, and requirements. About the Role You'll be a technical leader for a full-stack product engineering team, shaping the platform that empowers customers to create and optimize their AI agents. This means working closely with the Agent Software Engineering and Agent PM teams to understand current workflows, then defining technical strategy and establishing patterns that scale those capabilities across our customer base. You'll work day-to-day with the core product and design teams, joining discovery, defining requirements, reviewing designs, an

About Decagon Decagon is the leading conversational AI platform empowering every brand to deliver concierge customer experiences. Our technology enables industry-defining enterprises like Avis Budget Group, Block’s Cash App and Square, Chime, Oura Health, and Hunter Douglas to deploy AI agents that power personalized, deeply satisfying interactions across voice, chat, email, SMS, and every other channel. We’re building a future where customer experiences are being redefined from support tickets and hold music to faster resolutions, richer conversations, and deeper relationships. We’re proud to be backed by world-class investors who share that vision, including a16z, Accel, Bain Capital Ventures, Coatue, and Index Ventures, along with many others. We’re an in-office company, driven by a shared commitment to excellence and velocity. Our values — Just Get It Done, Invent What Customers Want, Winner’s Mindset, and The Polymath Principle — shape how we work and grow as a team. About the Team The Agent Product Engineering team at Decagon deploys mission-critical AI agents to our customers that impact millions of users and directly drive Decagon’s growth. You will build on our industry-leading AI agent platform, collaborate directly with customers and use your own creativity to devise long-term, scalable solutions. Our mission is to deliver magical support experiences — AI agents working alongside human agents to help users resolve their issues. About the Role On the Agent Product Engineering team, you’ll have complete ownership and autonomy in building and shipping best-in-class AI agents, from initial implementation through continuous iteration. You’ll work directly with leaders across industries like finance, healthcare and hospitality, solving their users’ needs with reliable and intuitive AI agents. Engineers here own their work end-to-end and are trusted to make a real impact. This role is for someone who dives deep into complex system challenges and builds elegant s