Principal Software Engineer, Experimentation Platform

Become a part of our caring community Every large organization is making critical decisions today about how it will leverage AI over the next decade. Few have leaders who can both define that vision and demonstrate its viability through hands-on engineering. This role requires both. We build the platform that transforms millions of clinical documents into trusted, actionable data. Our systems use large language models (LLMs) to read medical records, extract structured facts, answer complex questions with citations to source documents, and route difficult cases to human experts. These capabilities support decisions that impact real healthcare outcomes for members. As a Principal AI Applied Engineer, you will define the technical strategy, architectural standards, and long-term vision for AI-enabled products across the organization. You will influence enterprise-wide decisions regarding AI platforms, model strategies, engineering standards, and technology investments while remaining deeply hands-on in prototyping, experimentation, architecture, and software development. This is the highest-level individual contributor role within the AI Applied Engineering organization. Success requires exceptional technical depth, organizational influence, strategic thinking, and the ability to translate emerging AI capabilities into scalable, reliable, and responsible production systems. Why Join Us Shape the long-term AI architecture and engineering direction for a large enterprise healthcare organization. Influence how AI-enabled products are designed, built, evaluated, deployed, and governed across multiple teams. Drive strategic decisions involving models, vendors, platforms, infrastructure, and shared capabilities. Prototype and validate emerging technologies before the organization invests at scale.</

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

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 Product Engineering at Decagon builds all aspects of the platform our customers use to create, operate, and improve their AI agents. We turn work that currently requires an engineer into product that a CX team can run themselves. This team is core to how Decagon scales. The frameworks we build support every agent we have in production, each with its own workflows, data, and constraints. We build the agents too, and that’s what keeps the platform honest: a failure mode we debug in production becomes a guardrail, an eval, or a piece of tooling that catches it everywhere. Our agents run for companies like Hertz, American Airlines, and Notion across chat, voice, email, and SMS. About the Role You’ll design and build the systems that let customers configure, train, test, and monitor sophisticated AI agents with confidence. That means strong engineering underneath, and abstractions on top that hold up across different use cases without forking per customer. You’ll work day to day with prod

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

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 Product Engineering at Decagon builds all aspects of the platform our customers use to create, operate, and improve their AI agents. We turn work that currently requires an engineer into product that a CX team can run themselves. This team is core to how Decagon scales. The frameworks we build support every agent we have in production, each with its own workflows, data, and constraints. We build the agents too, and that’s what keeps the platform honest: a failure mode we debug in production becomes a guardrail, an eval, or a piece of tooling that catches it everywhere. Our agents run for companies like Hertz, American Airlines, and Notion across chat, voice, email, and SMS. About the Role You’ll design and build the systems that let customers configure, train, test, and monitor sophisticated AI agents with confidence. That means strong engineering underneath, and abstractions on top that hold up across different use cases without forking per customer. You’ll work day to day with prod

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 As a Senior Software Engineer on the Enterprise Product team, you will take ownership of designing and building robust, scalable systems that allow customers to create and optimize their AI agents with confidence. This means working closely with customer facing teams to understand current workflows, then designing elegant abstractions and interfaces 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,