Principal Software Engineer

Grubhub Holdings Inc.; Chicago (IL); On-site; USD 244,000 - 254,000; Full time

Job summary

Wonder is seeking a Principal Engineer to set the technical direction for its AI-native developer tooling from day one. You’ll define architecture to connect AI tooling to Wonder’s codebases, guide delivery of context aggregation, MCPs/CLIs, and sub-agents, and shape AI-assisted workflows developers rely on daily.

You’ll partner with engineers across teams, translate complex tradeoffs into standards, and mentor others while building scalable, auditable patterns for code generation, review,

Qualifications

• 10+ years of professional software engineering experience.
• Hands-on work with or on top of LLM-based tooling (agents, MCP servers, coding assistants, or similar).
• Direct experience integrating AI tools into real development workflows at scale.
• Strong system design skills with ownership of tools/platforms end-to-end.
• Ability to operate with ambiguity in a new team and shape playbooks.
• Experience designing and consuming APIs, webhooks, or integration systems.
• Experience building developer tooling, CI/CD systems used by engineers.
• Experience with Java/JVM and/or Python is a plus.

Responsibilities

• Define architecture for context aggregation, MCPs/CLIs, skills, and sub-agents to give AI tooling access to Wonder's codebases and systems.
• Set the direction for autonomous development agents and cloud agent solutions with proper access controls.
• Translate emerging AI patterns into standards that fit Wonder's stack, scale, and constraints.
• Define strategy for pre-review/triage tooling to automate mechanical and policy checks.
• Define architecture for systems that optimize AI costs and measure developer velocity.
• Set technical direction for developer tooling and ensure cross-team delivery in production.
• Write strategy docs and mentor senior engineers in durable AI-assisted engineering practices.

Skills

LLM tooling experience

AI tool integration

System design

API integration

Dev tooling / CI/CD

Java/Python

Communication

Education

Bachelor's or Master's in CS

Job description

About Wonder

Wonder Everything’s on the menu at Wonder. Except compromise. Wonder is the mealtime platform built to feed every craving in one order. With Wonder, you can mix and match hundreds of dishes from 20+ exclusive restaurants in a single order, so everyone gets exactly what they’re craving. Enjoy everything from tacos to Thai with $0 delivery fees, plus dine-in or pick up at a Wonder location near you. Each dish is made to order on-site by our culinary team and served hot. Behind the scenes, Wonder owns and operates every step of the dining experience, from recipe development to the technology that powers our experience, allowing us to deliver quality, variety, and consistency at scale. Join us as we work to make great food more accessible.

About The Opportunity

We're looking for a Principal Engineer to set the technical direction for this team from its earliest days and bring AI-enabled development practices to Wonder Engineering. You'll define the architecture for and guide delivery of solutions to solve context fragmentation, MCPs/CLIs, skills, sub-agents, and integrations that connect AI tooling to Wonder's codebases and systems, and the AI-assisted workflows — code generation, review, testing, documentation, refactoring, on-call/incident management — that engineers use every day. We’re looking for someone who brings proven AI-tooling developer patterns and practices from outside Wonder that we haven't yet discovered internally. You'll partner closely with the team's other engineers across the company, each of whom owns a distinct part of the developer-experience surface area, with senior engineering leadership, and with the platform, infrastructure, and application teams whose workflows you're improving.

Impact

Set the Architecture for AI-Native Developer Tooling: Define the architecture for and guide delivery of context aggregation solutions, MCPs/CLIs, skills, and sub-agents that give AI coding tools sanctioned, reliable access to Wonder's codebases, services, and systems.

Set the direction for Wonder's autonomous development agents and cloud agent solutions, including access controls and guardrails.

Bring Outside Patterns In: Bring a sharp point of view on where AI-assisted development actually creates leverage across review, testing, code generation, and documentation, and translate the best emerging practices into standards that fit Wonder's stack, scale, and constraints.

Raise the Ceiling on Review: Set the strategy for pre-review and triage tooling that clears and automates mechanical and policy issues before a human looks, and define standards for reviewing AI-generated code across Wonder Engineering.

Instrument for Efficiency, Not Just Adoption: Define the strategy and architecture for the systems that optimize AI costs across the org and abstract model selection away from engineers' day to day, so the platform routes each task to the right model at the right cost without every engineer having to reason about it. Define and measure developer velocity, tying AI spend to the outcomes it produces.

Guide Technical Outcomes: Set technical direction for developer tooling and ensure each team's deliverables add up to a complete cross-team solution, weighing tradeoffs (including build vs. buy, cost, and risk) and partnering with platform, infrastructure, and application teams and engineering leadership to land it in production.

Communicate Effectively: Write clear strategy docs, specs, and documentation, and provide, seek, and incorporate feedback from a team and organization still defining its own practices. Translate complex technical tradeoffs for audiences across departments and leadership levels, and mentor senior engineers in building durable, auditable AI-assisted engineering practices.

What You Bring to the Table

• Bachelor's or Master's degree in Computer Science or a related field, or equivalent practical experience.
• 10+ years of professional software engineering experience, including recent, hands‑on work building with or on top of LLM‑based tooling (agents, MCP servers, coding assistants, or similar).
• Direct experience integrating AI tools into real development workflows — code review, testing, code generation, or documentation — beyond individual use as an end user, ideally at organizational scale.
• Strong system design skills and a track record of owning tools or platforms end-to-end, from design through adoption across multiple teams.
• Comfort operating with ambiguity: this is a new team without established playbooks, and you'll be shaping them.
• Experience designing and consuming APIs, webhooks, or other integration/message‑based systems.
• Experience building developer tooling, internal platforms, CI/CD systems, or other software used by engineers as its primary users.
• Experience with Java/JVM and/or Python is a plus, though not required.
• A pragmatic approach to problem solving and the ability to troubleshoot complex technical obstacles.
• Excellent communication and interpersonal skills, including the ability to drive technical discussions with engineers and leaders across multiple teams, up to the senior director level.

Salary

Illinois Base Salary: $244,000 -$253,500. Wonder uses geographic‑specific salary structures, which means the salary offered may vary depending on where the job is located. The final salary offer will take into account various factors, such as the candidate's skills, education, training, credentials, and experience.

Benefits

The benefits applicable to this role include a competitive compensation package with equity and a 401(k). We also offer a choice of medical, dental, and vision plans, company paid short and long term disability coverage, paid time off including flexible time off for exempt employees, paid vacation for non‑exempt employees, and paid sick leave in compliance with applicable law in addition to paid parental leave, discounted meals and exclusive perks across the Wonder family of brands. Eligibility, effective dates, and available plan options vary by employment classification and location. To learn more about benefits for this role, visit our Careers page here.

Final Note

At Wonder, we build the best teams by hiring with an objective lens — evaluating people for their potential while championing diversity, equity, and inclusion. We do not discriminate based on race, color, religion, gender identity or expression, sexual orientation, national origin, age, military service eligibility, veteran status, marital status, disability, or any other protected class. As part of our commitment to fair and compliant hiring practices, Wonder participates in the federal government’s E‑Verify program to confirm employment eligibility. If you need an accommodation during the interview process, please let your recruiter know. Wonder is the mealtime platform built to feed every craving without compromise. With options including dine‑in, delivery, pickup, and meal kits, Wonder makes every mealtime effortless. Through the Wonder app, customers can combine hundreds of dishes from exclusive, chef‑developed concepts in a single order so everyone gets exactly what they’re craving. Wonder’s portfolio of brands includes meal‑kit pioneer Blue Apron, leading online food marketplaces Grubhub and Seamless, and Emmy®‑winning media company Tastemade. Together, we’re united by a single mission: to make great food more accessible. There has never been a more exciting time to join our world‑class team. We’ve brought together people who are changing the way the world eats — with grit, optimism, care, and a little bit of salt, and pepper. And we’re just getting started.