Staff Software Engineer, Retirement AI

Gusto, Inc.; Quinte West; On-site; CAD 266,000 - 404,000; Full time

Job summary

Gusto Retirement is seeking a senior software engineer to ship real, user-facing AI features. You will own end-to-end delivery, write production-ready code, and iterate with a small, senior team on language-model powered experiences.

You will partner with product and design to shape scope, implement LLM-driven flows, and ensure robust integration with existing systems. The role emphasizes pragmatism, bias to action, and clear communication.

Qualifications

• 7+ years of software engineering experience shipping production products.
• Hands-on experience implementing LLM-powered features and workflows.
• Strong services and APIs, data flows, and production-grade code.
• Experience leading sprint execution with Jira and cross-functional teams.
• Bias to action with strong written and verbal communication.
• Proficiency in Ruby on Rails or similar languages and React.

Responsibilities

• Design, build, and ship production features that use large language models.
• Implement and integrate LLMs (prompting, tool loops, evaluation, monitoring).
• Make pragmatic architecture decisions and keep projects unblocked.
• Partner with product and design to refine ideas and scope.
• Collaborate with other teams to integrate with existing systems.
• Write clear, reliable, well-tested code that scales.

Skills

LLM features

Team execution

Ruby on Rails

React

Jira

Bias to action

Communication

Job description

About Gusto

At Gusto, we're on a mission to grow the small business economy. We handle the hard stuff — payroll, health insurance, 401(k)s, and HR — so owners can focus on their craft and their customers. With teams in Denver, San Francisco, and New York, we support more than 500,000 small businesses nationwide and are building a workplace that reflects the people we serve.

All full-time employees receive competitive base pay, benefits, and equity (RSUs) — because everyone who helps build Gusto should share in its success. Offer amounts are determined by role, level, and location. Learn more about our Total Rewards philosophy.

AI is a fundamental part of how work gets done at Gusto. We expect all team members to actively engage with AI tools relevant to their role and grow their fluency as the technology evolves. AI experience requirements vary by role and will be assessed during the interview process.

About the Role:

You're a key engineer helping us ship real, user-facing AI at Gusto Retirement. This role is all about bias to action: owning problems end-to-end, getting working software in front of customers, and iterating quickly. You'll work closely with a small, senior team to implement language‑model‑powered experiences. If you like being hands‑on, making pragmatic technical decisions, working closely with product & design partners, and turning ideas into production features, you'll be a great fit.

About the Team:

We're a small, focused AI product team building practical, high-impact experiences to help people save for retirement at Gusto Retirement. The team is senior, collaborative, and very execution-focused—PMs bring strong ideas, and we own the execution fully. We work closely with product, design, and partner engineering teams, but keep tight ownership of our priorities and roadmap.

Here’s what you’ll do day-to-day:

• Design, build, and ship production features that use large language models to solve real customer problems.
• Implement and integrate LLMs (prompting, tool loops, evaluation, monitoring, etc).
• Make pragmatic architecture decisions, de-risk tricky areas, and keep the work unblocked.
• Partner with product and design to refine ideas, shape scope, and iterate quickly on end-to-end experiences.
• Collaborate with other engineering teams to integrate with existing systems and unblock dependencies.
• Write clear, reliable, well‑tested code that ships quickly and scales well.

Here’s what we're looking for:

• 7+ years of software engineering experience building and shipping production products or platforms
• Hands‑on experience implementing LLM‑powered features (e.g., RAG flows, agents, tool loops, workflow automation with language models, etc)
• Strong engineering skills (e.g., services, APIs, data flows); comfortable spending most of your time coding.
• Experience running or heavily contributing to a team’s execution: sprints, Jira, scoping, and cross‑functional coordination.
• Bias to action: you default to trying things, iterating, and learning, rather than getting stuck in analysis or waiting for direction.
• Clear communicator who can work well with product, design, and other engineering teams without needing a formal management title.
• Experienced with Ruby on Rails (or any comparable language), React (or any comparable library).

Our cash compensation amount for this role is targeted at $187,000-$234,000 in Denver & most remote locations, and $227,000-$284,000 for San Francisco & New York. Stock equity is additional. Final offer amounts are determined by multiple factors including candidate experience and expertise and may vary from the amounts listed above.

Gusto has physical office spaces in Denver, San Francisco, and New York City. Employees who are based in those locations will be expected to work from the office on designated days approximately 2-3 days per week (or more depending on role). The same office expectations apply to all Symmetry roles, Gusto's subsidiary, whose physical office is in Scottsdale.

Note: The San Francisco office expectations encompass both the San Francisco and San Jose metro areas.

When approved to work from a location other than a Gusto office, a secure, reliable, and consistent internet connection is required. This includes non-office days for hybrid employees.

Our customers come from all walks of life and so do we. We hire great people from a wide variety of backgrounds, not just because it's the right thing to do, but because it makes our company stronger. If you share our values and our enthusiasm for small businesses, you will find a home at Gusto.

Gusto is proud to be an equal opportunity employer. We do not discriminate in hiring or any employment decision based on race, color, religion, national origin, age, sex (including pregnancy, childbirth, or related medical conditions), marital status, ancestry, physical or mental disability, genetic information, veteran status, gender identity or expression, sexual orientation, or other applicable legally protected characteristic. Gusto considers qualified applicants with criminal histories, consistent with applicable federal, state and local law. Gusto is also committed to providing reasonable accommodations for qualified individuals with disabilities and disabled veterans in our job application procedures. We want to see our candidates perform to the best of their ability. If you require a medical or religious accommodation at any time throughout your candidate journey, please fill out this form and a member of our team will get in touch with you.

Gusto takes security and protection of your personal information very seriously. Please review our Fraudulent Activity Disclaimer.

Personal information collected and processed as part of your Gusto application will be subject to Gusto's Applicant Privacy Notice.