Senior Software Engineer II, AI Developer Foundations

<h4><span style="color: #000000;">About Us</span></h4> <p><span style="color: #000000;">At SimplePractice, we are improving access to quality care by equipping health and wellness clinicians with all the tools they need to thrive in private practice.</span></p> <p><span style="color: #000000;">More than 260k providers trust SimplePractice to build their business through our industry-leading software with powerful tools that simplify every part of practice management. From admin work to clinical care, our suite of innovative solutions work together to reduce administrative burden, empowering solo and small group practitioners to thrive alongside their clients.</span></p> <p><span style="color: #000000;">Award-winning and people-first, SimplePractice is shaping the future of health tech. Recognized by MedTech Breakthrough, the Digital Health Awards, and BuiltIn's Best Places to Work.</span></p> <h4><span style="color: #000000;">Our Culture</span></h4> <p><span style="color: #000000;">At SimplePractice, culture is our foundation. It influences the way we work, how we serve our customers, and how we approach accomplishing our mission. We have five core values that we strive to embody every day:</span></p> <ul> <li style="color: #000000 !important;"><span style="color: #000000;">We think big </span></li> <li style="color: #000000 !important;"><span style="color: #000000;">We take simplicity seriously </span></li> <li style="color: #000000 !important;"><span style="color: #000000;">We come as we are </span></li> <li style="color: #000000 !important;"><span style="color: #000000;">We act with humility </span></li> <li style="color: #000000 !important;"><span style="color: #000000;">We are built on trust</span></li> </ul> <p><span style="color: #000000;">Culture is everyone's responsibility at SimplePractice. Our culture is what drives us to do better for our teammates and customers.</span></p> <p><span style="color: #000000;">Connection and collaboration are also key to our success. You will work with our talented multi-national teams and have opportunities to participate in onsites in both the US and Mexico.</span></p> <h4><span style="color: #000000;">The Role</span></h4> <p><span style="color: #000000;">Engineers on the AI Developer Foundations will build the tools that build the product. It's a new team that owns how AI gets used inside engineering, product, and design at SimplePractice: the conventions for using these tools, the context agents read before they touch our code, the bar generated work has to clear before a human spends time on it, and the training that makes AI a useful tool to all of engineering.</span></p> <p><span style="color: #000000;">This is a hands-on role reporting to the VP of Technology. You'll write code most days, mostly in and around a large Rails monolith, and you'll also write the conventions other engineers follow. </span></p> <h4><span style="color: #000000;">Responsibilities</span></h4> <ul> <li style="color: #000000 !important;"><span style="color: #000000;">Own the context layer agents read: rules files, docs conventions, grounding data, with CI and named owners keeping it current</span></li> <li style="color: #000000 !important;"><span style="color: #000000;">Publish the standards for how we prompt coding agents, how we supply context, and what a spec needs to contain before it's worth handing to an agent</span></li> <li style="color: #000000 !important;"><span style="color: #000000;">Define the review gates any AI-generated artifact clears before a human spends time on it, and get what reviewers catch flowing back into the conventions</span></li> <li style="color: #000000 !important;"><span style="color: #000000;">Take the prototypes running today and turn the ones that hold up into supported workflows that run for someone other than their author</span></li> <li style="color: #000000 !important;"><span style="color: #000000;">Evaluate harnesses, models and vendors against criteria and eval sets</span></li> <li style="color: #000000 !important;"><span style="color: #000000;">Work the product-to-engineering handoff with PMs, designers and EMs</span></li> <li style="color: #000000 !important;"><span style="color: #000000;">Teach. Documentation, worked examples, office hours, and time sitting with a squad while they work with the tools we build</span></li> <li style="color: #000000 !important;"><span style="color: #000000;">Help us draw the boundaries for where an agent runs unattended, where a human signs off, and where we don't use one at all</span></li> </ul> <h4><span style="color: #000000;">Desired Skills & Experience</span></h4> <p><span style="color: #000000;"><strong>Education & Experience</strong></span></p> <ul> <li style="color: #000000 !important;"><span style="color: #000000;">BS/MS in Engineering, Computer Science, or related field, or equivalent experience</span></li> <li style="color: #000000 !important;"><span style="color: #000000;">7+ years building production software and then maintaining it. You’ve shipped something, lived with the decisions, and found out whether a design decision held up</span></li> <li style="color: #000000 !important;"><span style="color: #000000;">Strong problem-solving and communication skills; comfortable in fast-paced, cross-functional environments</span></li> </ul> <p><span style="color: #000000;"><strong>Ruby on Rails</strong></span></p> <ul> <li style="color: #000000 !important;"><span style="color: #000000;">Recent, direct Rails experience in a large codebase.</span></li> <li style="color: #000000 !important;"><span style="color: #000000;">Ability to read unfamiliar application code quickly and judge whether what an agent produced in it is any good</span></li> </ul> <p><span style="color: #000000;"><strong>AI-Assisted Engineering</strong></span></p> <ul> <li style="color: #000000 !important;"><span style="color: #000000;">LLM-backed systems you've shipped to users and kept running, past the point where better prompting stops helping</span></li> <li style="color: #000000 !important;"><span style="color: #000000;">Experience building context or memory handling, and writing evals</span></li> <li style="color: #000000 !important;"><span style="color: #000000;">Judgment about what belongs in code and what belongs in the model</span></li> <li style=&quo