Senior Software Engineer in Test

About Chowly

Chowly is an all-in-one digital restaurant ordering platform that specializes in bringing enterprise-grade software to independent operators and emerging brands. Our mission is to simplify restaurant technology.

Chowly has quickly amassed over 17,000 restaurants on its platform, all with deeply integrated software embedded in the restaurants' technology stacks. These include some of the fastest-growing brands in the country, like Mod Pizza and many others. Chowly's best-in-class partnership ecosystem (including DoorDash, Toast, Uber Eats, Square, and others) has created an exciting opportunity to accelerate our growth further.

We seek a highly skilled and motivated Senior Software Engineer in Test to collaborate with our close-knit and agile Engineering Team. This individual will work with other engineers, product managers, and stakeholders to build and own the automated testing and quality infrastructure that protects Chowly's platform and its partner integrations.

YOU ARE

• Collaborative and have experience working with cross-functional teams to gather and refine requirements, ensuring alignment with overall business goals and customer needs
• An engineer first, you write production-quality test code, not just test cases
• Detail-oriented and write clean, maintainable, and well-structured code, adhering to best practices and industry standards
• Skeptical by instinct, you look for the edge case, the race condition, and the partner API that returns something undocumented
• Able to reason about risk and prioritize what matters most when full coverage isn't possible
• Independent and work well under occasional pressure in a fast-paced environment

YOU WILL

• Design, build, and own Chowly's automated test suites across the unit, API, service, and end-to-end layers
• Build and maintain integration test coverage for our partner ecosystem (DoorDash, Toast, Uber Eats, Square), including mocks, sandboxes, and contract tests that catch breaking partner changes before our customers do
• Establish and enforce quality gates in CI so regressions are caught on the pull request, not in production
• Build reliable test data and test environment tooling, so suites are repeatable rather than flaky
• Investigate, triage, and root-cause failures, and drive them to resolution with the owning engineer
• Develop and maintain technical documentation covering test strategy, coverage, and how to run and extend the suites
• Review fellow team members' work through code reviews, with a focus on testability and coverage
• Report on quality signals - coverage, flake rate, escaped defects, so the team can act on them

REQUIREMENTS

• 4+ years of professional software development experience, with a substantial portion focused on test automation
• Proven ability to write and maintain automated tests in a production codebase, including:
• Ruby and RSpec (Chowly's backend is Ruby on Rails with Sidekiq)
• An end-to-end browser framework such as Playwright or Cypress
• REST API and integration testing, including mocking and stubbing third-party services
• Experience working with relational databases such as MySQL, MSSQL, or PostgreSQL, and writing SQL to validate data
• Experience building and maintaining CI pipelines - GIT, GitHub Actions, DevOps, CICD
• Comfortable using AI coding assistants to accelerate test authoring and failure triage, while applying your own judgment to test strategy, risk analysis, and architecture
• Exceptional problem-solving skills with the ability to think critically and creatively to develop innovative solutions

EVEN BETTER IF YOU

• Have tested high-volume third-party API integrations, or a partner or marketplace platform
• Have built AI-assisted quality tooling - automated test generation, self-healing selectors, or LLM-based validation of outputs that don't have a single correct answer
• Have experience testing asynchronous, queue-based systems such as Sidekiq
• Have exposure to Cloud development methodologies and their associated environments, such as Azure and AWS
• Have a conceptual understanding of front-end technology to include React, HTML5/CSS, etc.
• Have experience with performance or load testing
• Have worked in restaurant technology, payments, or POS integrations

Perks and Benefits

We offer a competitive salary as well as:

• Remote first team (Chicago office space is available, but the team is entirely remote.)
• Unlimited Paid Time Off
• Parental & Holiday Leave
• 401(k) Plan
• Health & Wellness Stipend
• Robust Medical, Dental, & Vision Insurance (100% employer-paid employee medical insurance & 50% employer-paid dependents)
• Employer-Sponsored Basic Life, Short-Term, & Long-Term Disability Insurance

We’re an equal opportunity employer and comply with all applicable federal, state, and local fair employment practices laws. We strictly prohibit and do not tolerate discrimination against employees, applicants, or any other covered persons because of race, color, religion, creed, national origin or ancestry, ethnicity, sex, gender (including gender nonconformity and status as a transgender individual), sexual orientation, marital status, age, physical or mental disability, citizenship, past, current or prospective service in the uniformed services, predisposing genetic characteristic, domestic violence victim status, arrest records, or any other characteristic protected under applicable federal, state or local law.