Senior Software Engineer (Python/.NET)

ShiftKey Engineering Team Lead

ShiftKey's scheduling platform is the backbone of what we do - and we're in the middle of making it dramatically better. We've made a deliberate, focused decision to double down on the platform at heart of our product: modernizing the codebase, improving supportability, and building a foundation we can confidently evolve and ship features from for years to come. This isn't a greenfield rewrite for its own sake - it's a pragmatic, high-impact investment in software that real customers depend on every day. You'd be joining a tight, experienced engineering squad - 6 to 7 senior engineers spanning multiple products and stacks - at a genuinely defining moment for the platform. This isn't maintenance mode: you're shaping architecture, setting standards, and leaving real fingerprints on a product customers depend on daily. The team has also fully committed to an AI-accelerated SDLC - Claude Code, agent orchestration, LLM tooling - not as an experiment, but as how we actually build software. And the people make it worth showing up: experienced, coordinated, low-ego, and genuinely collaborative.

This is a fully remote position based in the United States. You should be comfortable working asynchronously and partnering with teammates in different time zones.

Lead backend development on our core scheduling platform modernization - setting Python best practices, guiding architecture decisions, and owning the quality of Python-driven services as the system evolves.

Contribute across a multi-product ecosystem (Engage, Auth, Messaging, Time) that spans Python and .NET - this role is built for engineers who thrive across stacks, not single-use specialists.

Write APIs, own services review code, and ship - the full range of what senior engineering looks like in practice.

Help drive the team's evolution toward an AI-accelerated SDLC, using tools like Claude Code to orchestrate agents that write, debug, and test software - this is an active part of how we work, not a future ambition.

Deep, production-grade Python experience (Python 3.10+) - you write clean, idiomatic code and you've set the standard for it on a team before.

Meaningful.NET exposure - enough to contribute across our existing product suite and feel comfortable in a mixed-stack environment.

Hands-on experience with AI-assisted or agentic development workflows - LLM tooling, multi-agent systems, or similar; you're already working this way or actively have been.

The kind of senior judgment that shows up as good instincts, constructive disagreement, and initiative without needing to be the loudest person in the room.

A genuine team-first orientation - ShiftKey engineering runs on collaboration, and we hire for it deliberately.

Inclusive and collaborative work environment where all voices are valued.

Hybrid-friendly office spaces designed to be fun and engaging.

Comprehensive health, vision, and dental coverage.

Benefits begin on your first day.

Generous PTO and company-paid holidays, including flexible floating holidays.

100% 401(k) employer match up to 6%.

Paid parental leave.

Wellness support, including access to mental health resources.

ShiftKey is an equal opportunity employer and is committed to embracing diverse and individual perspectives shaping our culture and contributing to the solutions that transform the world. We actively work to create an inclusive environment for employees to thrive.

ShiftKey does not discriminate based on race, religion, color, sex, gender, gender identity, sexual orientation, age, non-disqualifying physical or mental disability, national origin, veteran status, or any other basis covered by applicable law. All employment is decided based on qualifications, merit, and business needs. ShiftKey is committed to providing reasonable accommodation to applicants with a mental or physical disability, please contact: View email address on click.appcast.io