Senior Director of Engineering, Developer and Agent Experience

Toast, Inc.

Confirmed live yesterday High trust
Remote

Quick summary

Work type
Remote
Location
Remote
Salary
$314,000–$502,000 / yr
Posted
45 days ago
Freshness
Confirmed live yesterday
Closes
Dec 8, 2026

Market check

Salary context

Above market

How this pay compares to similar roles

Similar $224k
This role $408k
$146k most similar roles pay here $540k

This role pays more than 99% of similar roles. Most pay $183,987–$263,400 — the shaded band above. At the midpoint, this role pays about $408k versus about $224k for comparable roles.

Based on 240 similar postings.

Employer

About Toast, Inc.

Toast is a cloud-based restaurant management platform providing point-of-sale, payment processing, and operations software for the food service industry.

Toast, Inc. currently has 29 open roles on FindRole.

Listed pay typically runs $190,000–$304,000 across 29 roles with salary data.

Most-posted roles

View all roles at Toast, Inc.

At a glance

TL;DR · Senior Director of Engineering, Developer and Agent Experience

As the Senior Director of Engineering, Developer and Agent Experience, you will lead the development of an AI-native engineering operating system to transform how software is built from idea to production. You will build and manage a specialized organization focused on AI platform engineering, agent systems, and developer experience integration. Your daily responsibilities include designing and implementing AI-driven development systems, managing model access layers for LLMs, and re-architecting the inner and outer loops of the developer experience to automate code generation, testing, and deployment. You will utilize skills in applied AI, agentic architectures, prompt engineering, and context design while navigating compliance constraints like PCI and SOX. The role solves the challenge of transitioning individual AI tool usage into standardized, scalable workflows across the software development lifecycle and product development lifecycle for a large R&D ecosystem.

What you'll do

  • Build and manage an AI-native engineering operating system to automate the software development lifecycle from idea to production.
  • Develop core platforms including model access layers, agent orchestration systems, and internal AI marketplaces.
  • Design automated workflows that convert product requirements and design specifications into executable code, tests, and documentation.
  • Re-architect developer experience across inner and outer loops to reduce friction in code reviews and deployment.
  • Standardize AI tool usage across the organization by establishing playbooks, training, and technical guardrails.
  • Manage model-cost optimization, routing, and governance for all internal AI systems.
  • Build and lead a specialized team focused on AI platform engineering and developer experience integration.
  • Architect model-agnostic infrastructure to ensure portability across different LLMs and vendors.

What we're looking for

  • You must possess deep technical proficiency in applied AI and agentic architectures as an internal authority.
  • You must have 15+ years of experience in software engineering, including senior leadership roles.
  • You must have proven experience building and scaling developer platforms, internal engineering systems, and CI/CD pipelines.
  • You must be able to design end-to-end workflows and systemic, long-term platforms rather than point solutions.
  • You must be familiar with prompt engineering, context design, and usage-based cost models for platform governance.
  • You must have a proven capability to drive organization-wide adoption of new tools and standards across large R&D ecosystems.
  • You must have experience operating within real compliance constraints such as PCI or SOX.

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