Director of Agent Deployment Engineering

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

Over the past few years, development of LLMs has evolved at a rapid pace. It’s not enough for our customers to just “set it and forget it” when it comes to AI software. Truly successful AI Agents require hands-on execution, rigorous iteration, and deep technical delivery to reach enterprise-grade performance.

We’re creating an Agent Deployment Engineering Org: a specialized technical delivery team responsible for end-to-end execution of AI agent builds. Agent Deployment Engineers own the hands-on work required to deliver best-in-class agents—writing and configuring key components, validating integrations, and ensuring agents perform reliably at scale. This team brings greater specialization and focus to build quality. Agent Deployment Engineers are technical and customer-facing: interfacing with senior technical stakeholders while going deep on agent configuration and build execution.

About the Role

As Director of Agent Deployment Engineering, you will lead Decagon’s technical delivery for strategic enterprise customers—owning outcomes across multiple deployments and building the team, playbooks, and operating system required to scale. This is a senior, customer-facing leadership role where you’ll partner with customer executives and technical leaders to define success, translate requirements into delivery plans, and drive launches that measurably impact customer outcomes.

You’ll work closely with Agent PMs, Agent Success, Engineering, and GTM leadership to create tight feedback loops: driving delivery, surfacing product gaps, and influencing the evolution of Decagon’s agent-building platform based on real enterprise needs. This role is ideal for a leader who thrives in fast-moving environments, enjoys shipping customer-facing technical work, and can balance hands-on problem solving with structured execution at scale.

In this role, you will

• Lead and scale a high-performing delivery org

  • Own end-to-end execution of AI agent deployments for enterprise customers across a portfolio, from scoping through launch and iteration.

  • Build, lead, and develop a team of Agent Builders; hire, coach, and set a high bar for quality, velocity, and customer outcomes.

  • Establish delivery operating rhythms (planning, reviews, retros), capacity planning, and forecasting to ensure predictable execution.

• Drive executive-level customer engagements

  • Interface with senior technical stakeholders and executives to define success criteria, align on constraints (security/compliance), and drive delivery against timelines.

  • Lead complex escalations and unblock cross-functional teams when quality, timelines, or customer outcomes are at risk.

  • Translate customer needs into crisp internal documentation and execution plans across Product/Engineering/GTM.

• Create repeatable playbooks and scale mechanisms

  • Define and standardize delivery methodologies and artifacts (e.g., AOP quality bar, launch readiness checklists, iteration loops).

  • Establish best practices for evaluation and guardrails to ensure safe, compliant, and predictable agent performance in real-world scenarios.

  • Improve tooling and processes to reduce time-to-launch and increase reliability across deployments.

• Influence the platform roadmap through deployment insights

  • Identify recurring product/platform gaps and drive prioritization with Engineering and Product leadership.

  • Partner with internal teams to turn real customer needs into platform improvements that compound across deployments.

Your background looks something like this

• 10+ years of relevant experience in technical, customer-facing roles (e.g., forward-deployed engineering, solutions engineering, technical consulting, implementation engineering, technical product/PM, or similar).

• 5+ years of people management experience, including hiring, coaching, performance management, and building high-performing teams; ideally experience leading senior ICs and/or managers.

• Strong technical foundation—comfortable working with APIs, integrations, and complex systems; able to go deep to diagnose issues and guide solution architecture.

• Experience delivering production-grade customer solutions that require structured execution, testing/validation, and iteration.

• Ability to communicate clearly with senior technical stakeholders, translate requirements into execution plans, and drive delivery.

• Comfort operating in fast-moving, ambiguous environments where you build structure while maintaining momentum.

Even better if you have

• Experience deploying LLM-based products or AI agents in production (prompting, evaluation, guardrails, tooling, workflow design).

• Experience with enterprise SaaS integrations (e.g., ticketing systems, CRM, data pipelines) and security/compliance considerations.

• Strong product instincts—ability to define success metrics, write crisp requirements, and contribute customer insight back into product roadmap.

• Experience scaling a delivery function from high-touch execution to repeatable playbooks and durable operating cadence.

Compensation

$250K – $320K + Offers Equity

Benefits

We proudly offer the following benefits for our full-time employees:

• Medical, Dental, and Vision benefits for you and your family

• Life Insurance and Disability Benefits

• Retirement Plan (e.g., 401K, pension)

• Parental Leave

• Fertility and family building benefits through Carrot

• Monthly stipend to support your wellness, lifestyle, and work-life balance

• Daily lunches and snacks in the office to keep you at your best

• Take what you need vacation policy (subject to local requirements; UK employees receive 25 days of statutory leave)

These benefits are described in more detail in Decagon’s policies, may vary by location, and can change at any time according to applicable compensation and benefits plans.