Staff Software Engineer

SimplePractice; United States; On-site; USD 249,000 - 311,000; Full time

Benefits offered by this job

Medical insurance

Dental insurance

Vision insurance

Life insurance

Disability insurance

401(k) match

Flexible PTO

Wellbeing days

Paid holidays

Summer Fridays

Mental health resources

Parental leave

Backup care

ERGs

Job summary

SimplePractice is expanding its AI developer foundations team to shape how AI is used inside engineering, product, and design. This hands-on role writes code around a Rails monolith and defines conventions for prompts, context, and evaluation gates.

You will collaborate with PMs, designers, EMs and other engineers, and help build trusted, maintainable AI-powered workflows for clinicians. You will contribute to context handling, documentation, and cross-functional enablement while ensuring safety

Qualifications

• BS/MS in Engineering, Computer Science, or related field, or equivalent experience
• 7+ years building production software and maintaining it, with evidenced decisions
• Strong problem-solving and communication skills in fast-paced environments

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

Skills

Rails

AI/ML Systems

Context memory

Documentation

Education

BS/MS in Engineering/CS

Equivalent experience

Tools

AWS

Terraform

Kubernetes

Docker

Job description

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 250,000 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. In 2026, we were recognized by BuiltIn as a Best Remote Company to Work For, Software Guru's Best Places to Code, Becker Healthcare Telehealth Companies to Know, and we won a MedTech Breakthrough Award for Best Practice Management Solution Provider.

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

• 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

Benefits

We offer a competitive benefits program including:

• 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 CareTuition reimbursement
• Employee Resource Groups (ERGs)

California Job Applicant Privacy Notice

Thank you for your interest in opportunities at SimplePractice LLC ("SimplePractice" or "us" or "we" or "our"). Please note that when you submit your resume or application materials to us for employment purposes, you are subject to the SimplePractice California Job Applicant Privacy Notice.

For more information about our privacy practices, please contact us at [e-mail].

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

$249,120 — $311,400 USD