[Hiring] Principal Software Engineer, Full-Stack @Ollie

Role Description

Ollie is seeking a Principal Software Engineer, within our Core Platform team, who thrives in a small team and is excited to learn from teammates in a collaborative environment. This position is great for you if you are a curious, collaborative, and open-minded engineer. You have built and used many APIs before, and know the pitfalls and challenges involved with supporting and scaling them in the real world. You are someone who loves programming and is passionate about making a better product. You use AI tools to boost your productivity and knowledge while maintaining strict quality control over its outputs. You enjoy delivering reliable, performant, well-tested code that powers all your clients!

This is a remote role based in the Northeast U.S., with monthly in-person co-working sessions. The position collaborates across the organization and reports to the Senior Technical Lead, Platform.

What You'll Do:

• Design, build, and maintain APIs, interfaces, and technical infrastructure that power Ollie’s subscription platform.
• Contribute to all stages of the software development lifecycle - from planning to implementation, deployment, and maintenance.
• Collaborate closely with engineers and product managers in an agile environment to deliver high-quality, impactful features.
• Develop and integrate 3rd-party services to enhance functionality and improve the customer experience.
• Write reliable, performant, and well-tested code that scales with our growing business.
• Continuously improve existing systems through refactoring, performance optimization, and automation.
• Participate in code reviews, knowledge sharing, and technical discussions to uphold best practices and foster team learning.
• Troubleshoot production issues and help maintain a stable and resilient platform.
• Stay curious - explore new tools, technologies, and techniques to improve developer experience and product quality.

Who You Are:

• You have 7+ years of professional experience building applications in a Python framework (Django, Flask, etc.).
• You have 10+ years of experience building API systems, including technologies such as REST, OAuth2 and integrations with 3rd party services using REST APIs and JSON.
• You have an understanding and professional experience working in a Javascript frontend framework (React, Angular, Etc.).
• You have an understanding of and professional experience using a relational database (PostgreSQL, MySQL, etc.) including SQL language.
• You have strong technical knowledge and deep understanding of time/maintainability/quality trade-offs.
• You have experience writing unit tests.
• You have experience with using version control (git, svn, etc.).
• You have excellent communication & collaboration skills.
• You have experience using AI models and tooling (Claude code, Cursor, etc.).
• You’re a self-starter, positive and excited to work with a small dedicated team.
• You are passionate about using technology to streamline business processes.

Bonus Points if:

• You’re a dog owner or lover.
• You have experience with Django.
• You have experience with React.
• You have experience with NodeJS.
• You have experience with Shopify.
• You have experience documenting with JSON Schema and OpenAPI.
• You have experience with Docker/Containerization.
• You are a master prompt writer.
• You are an open source community contributor.

What You'll Get:

• Competitive salary.
• Sponsored 401k program with employer match up to 4%.
• Comprehensive health coverage including medical, dental and vision.
• Unlimited vacation policy that you're encouraged to use.
• Paid parental leave.
• 1-week paw-ternity leave for new dog parents.
• Free Ollie subscription.
• Inspiring pack members!

What We Value:

• Keeping Dogs At The Heart: Our profound love for dogs unites us and drives and inspires every aspect of our business.
• Being Courageous And Kind: We create a safe, inclusive space for everyone to show up as their authentic selves.
• Setting New Standards: We believe in continually raising the bar, never settling for less than our best as a team and individuals.
• Making Ollie The Best Chapter: We are building an impactful business while making memorable experiences with one another.