Senior Director of Engineering, Developer and Agent Experience

United States Digital Space LLC; Dublin; Hybrid; EUR 121,000 - 190,000; Full time

Job summary

ToastTab is seeking a hands‑on Head of Developer & Agent Experience to lead the build of an AI‑native engineering operating system, shaping how ideas become production code. You will design systems, review architecture, and set platform direction with Product, Engineering, and Design.

You will own the inner and outer loop tooling, establish standards, dashboards, and cost governance, and build a focused team dedicated to AI platform engineering, agent systems, and developer experience

Qualifications

• 15+ years in software engineering, including senior leadership roles.
• Proven experience building and scaling developer platforms, internal engineering systems, CI/CD, build systems or platform tooling.
• Ability to design end‑to‑end workflows and systemic, long‑term platforms rather than point solutions or developer tooling.
• Familiarity with prompt engineering, context design, developer‑facing API/platform design and usage‑based cost models/platform governance.
• Proven capability to drive organization‑wide adoption of new tools, workflows, playbooks, and structural standards across a large, diverse R&D ecosystem.
• Experience operating inside real compliance constraints — PCI, SOX, or equivalent.

Responsibilities

• Define and deliver the core platform enabling AI‑native development, including the model access layer, agent orchestration, prompt frameworks and an internal AI marketplace.
• Design and implement AI‑driven development systems that convert PRDs and design specs into executable workflows.
• Re‑architect the developer experience across the inner loop and outer loop to reduce friction in PR creation, code reviews, and validation.
• Partner with Engineering, Product and Design leaders to transition AI tool usage into standardized workflows with training and playbooks.
• Define and monitor north‑star metrics and own dashboards and feedback loops to drive action.
• Build and lead a focused organization specialized in AI platform engineering, agent systems, and developer experience integration.
• Own the human‑facing developer experience alongside the agent‑facing one and establish durable operating contracts with Release Engineering.
• Architect for optionality and portability across models, vendors, and marketplace plugins.

Skills

Applied AI

Agent architectures

Platform tooling

Leadership

CI/CD systems

Tools

CI/CD tooling

Build systems

Code review tooling

Job description

the company creates technology to help restaurants and local businesses succeed in a digital world, helping business owners operate, increase sales, engage customers, and keep employees happy.

As the Head of Developer & Agent Experience, you will lead the development of the company’s AI-native engineering operating system—transforming how software is built from idea to production. This is a hands‑on leadership role. You will actively design and build systems, review architecture, and contribute to core platform direction, rather than operating purely through management layers.

This role is focused on systemizing AI across the software development lifecycle (SDLC), and product development lifecycle (PDLC) to turn tool usage into a scalable, standardized, and high-leverage engineering system. Partnering closely with senior technical leaders across Product, Engineering, and Design, you will define and deliver the platforms, workflows, and guardrails that enable teams to move from specification to code, test, and deployment with AI embedded at every step.

A day in the life (Responsibilities)

• Define and deliver the core platform enabling AI‑native development, including the model access layer (LLMs, routing, governance), agent orchestration systems (code, test, review, deploy), prompt/specification frameworks, coding harnesses and an internal AI marketplace

• Design and implement AI‑driven development systems that convert PRDs and design specs into executable workflows, enabling the automated generation of code, tests, documentation, and infrastructure

• Re‑architect the developer experience across the inner loop (local development, testing, iteration) and outer loop (CI/CD, deployment, release) to reduce friction in PR creation, code reviews, and validation

• Partner with Engineering, Product and Design leaders to transition individual AI tool usage into standardized workflows, establishing tooling defaults, playbooks, and training to ensure active AI usage across R&D

• Define and monitor the north‑star metrics and own the dashboards and feedback loops that turn them into action. This role owns model‑cost optimization, routing, and governance, while org‑wide spend and scorecard reporting sits with Technical Operations

• Build and lead a focused organization specialized in AI platform engineering, agent systems, automation and developer experience integration

• Own the human‑facing developer experience alongside the agent‑facing one: local development and inner‑loop tooling, the Developer Portal and service catalog, core libraries and service templates, schema‑first tooling, and authoritative service metadata — and establish a durable operating contract with Release Engineering for the delivery machinery underneath

• Architect for optionality rather than lock‑in: keep the harness layer model‑agnostic, evaluate open‑weight and self‑hosted options, and ensure marketplace skills, plugins, and agents remain portable across models and vendors

What you'll need to thrive (Requirements)

• You must possess deep technical proficiency in applied AI and agentic architectures, serving as the definitive internal authority.

• 15+ years in software engineering, including senior leadership roles, with a background in high‑velocity engineering organizations

• Proven experience building and scaling developer platforms, internal engineering systems, CI/CD, build systems or platform tooling

• Ability to design end‑to‑end workflows and systemic, long‑term platforms rather than point solutions or developer tooling

• Familiarity with prompt engineering, context design, developer‑facing API/platform design and usage‑based cost models/platform governance

• Proven capability to drive organization‑wide adoption of new tools, workflows, playbooks, and structural standards across a large, diverse R&D ecosystem

• Experience operating inside real compliance constraints — PCI, SOX, or equivalent — and a track record of reducing scope or negotiating defensible exceptions rather than accepting them as permanent blockers

AI at the company

At the company, one of our company values is that we're hungry to build and learn. We believe learning new AI tools empowers us to build for our customers faster, more independently, and with higher quality. We provide these tools across all disciplines, from Engineering and Product to Sales and Support, and are inspired by how our Toasters are already driving real value with them. The people who thrive here are those who embrace changes that let us build more for our customers; it's a core part of our culture.

Our Total Rewards Philosophy

We strive to provide competitive compensation and benefits programs that help to attract, retain, and motivate the best and brightest people in our industry. Our total rewards package goes beyond great earnings potential and provides the means to a healthy lifestyle with the flexibility to meet Toasters' changing needs. Learn more about our benefits at https://careers.toasttab.com/the company-benefits.

How the company Uses AI in its Hiring Process

Throughout the hiring process, our goal is to get to know you. We use AI tools to support our recruiters and interviewers with tasks like note‑taking, summarization, and documentation of interviews to ensure they can be fully focused on your conversation. All hiring decisions are made by people. To learn more: https://careers.toasttab.com/ai-in-hiring

Our Approach to Hybrid Working

We embrace a hybrid work model that fosters in‑person collaboration while valuing individual needs. Our goal is to build a strong culture of connection as we work together to empower the hospitality community, regardless of location. Please visit the Locations page on our career site to learn more about our in‑office expectations by region:https://careers.toasttab.com/locations-the company

Diversity, Equity, and Inclusion is Baked into our Recipe for Success

At the company, our employees are our secret ingredient—when they thrive, we thrive.The restaurant industry is one of the most diverse, and we embrace that diversity with authenticity, inclusivity, respect, and humility. By embedding these principles into our culture and design, we create equitable opportunities for all and raise the bar in delivering exceptional experiences.

We Thrive Together

We embrace a hybrid work model that fosters in‑person collaboration while valuing individual needs. Our goal is to build a strong culture of connection as we work together to empower the restaurant community. To learn more about how we work globally and regionally, check out: https://careers.toasttab.com/locations-the company.

the company is committed to creating an accessible and inclusive hiring process. As part of this commitment, we strive to provide reasonable accommodations for persons with disabilities to enable them to