Senior Software Engineer II, AI Developer Foundations

About Us

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. 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. 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.

Our Culture

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:

• We think big
• We take simplicity seriously
• We come as we are
• We act with humility
• We are built on trust

Culture is everyone's responsibility at SimplePractice. Our culture is what drives us to do better for our teammates and customers. 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.

The Role

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. 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.

Responsibilities

• Own the context layer agents read: rules files, docs conventions, grounding data, with CI and named owners keeping it current
• 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
• 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
• Take the prototypes running today and turn the ones that hold up into supported workflows that run for someone other than their author
• Evaluate harnesses, models and vendors against criteria and eval sets
• Work the product-to-engineering handoff with PMs, designers and EMs
• Teach. Documentation, worked examples, office hours, and time sitting with a squad while they work with the tools we build
• 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

Desired Skills & Experience

Education & Experience

• BS/MS in Engineering, Computer Science, or related field, or equivalent experience
• 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
• Strong problem-solving and communication skills; comfortable in fast-paced, cross-functional environments

Ruby on Rails

• Recent, direct Rails experience in a large codebase
• Ability to read unfamiliar application code quickly and judge whether what an agent produced in it is any good

AI-Assisted Engineering

• LLM-backed systems you've shipped to users and kept running, past the point where better prompting stops helping
• Experience building context or memory handling, and writing evals
• Judgment about what belongs in code and what belongs in the model
• Track record evaluating tools with evidence

Developer Tooling & Enablement

• Internal tools, platforms, conventions or workflows that other engineers chose to use
• CLI and harness-shaped software, and comfort connecting systems over APIs
• Strong writing. Much of this role is getting other people to work differently, which happens through docs and worked examples rather than announcements
• Comfort working outside engineering, explaining technical constraints to people who don't share your background and taking their pushback seriously

Bonus Points

• Agent harnesses, MCP servers, orchestration frameworks
• Healthcare or another HIPAA-regulated environment
• AWS, Terraform, Kubernetes, Docker
• Experience on a platform or infrastructure team where the customers were other engineers
• Having overbuilt a platform once before the workflows existed, and learning to spot the warning signs earlier

Our Stack

Ruby on Rails monolith, Aurora MySQL, Redis, Sidekiq, Ember.js, AWS (EKS, Bedrock and more). Linear, GitHub, Semaphore, Datadog, LaunchDarkly.

Benefits

• Medical, dental, vision, life & disability insurance
• 401(k) plan with company match
• Flexible Time Off (FTO), wellbeing days, paid holidays, and summer Fridays
• Mental health resources
• Paid parental leave & Backup Care
• Tuition reimbursement
• Employee Resource Groups (ERGs)

Pay

Base salary is one component of total compensation. Employees may also be eligible for an annual bonus or commission. Some roles may also be eligible for overtime pay. The amount below represents the expected annual base compensation range for this job requisition. Ultimately, in determining your pay, we'll consider many factors including, but not limited to, skills, experience, qualifications, geographic location, and other job-related factors. Base Compensation Range: $208,000 USD - $260,000 USD