Retirement AI Staff Engineer

The Wrap; New York (NY); Hybrid; USD 227,000 - 284,000; Full time

Benefits offered by this job

Equity (RSUs)

Benefits

Job summary

Gusto, a platform enabling small businesses with payroll, benefits, and HR, is hiring a senior engineer to ship AI-powered user experiences. You’ll own problems end‑to‑end and release working features to customers, iterating quickly in a senior, hands‑on team.

You’ll collaborate with product and design to deliver production-ready solutions using LLMs. We expect deep experience building production software, comfort with coaching peers, and a bias to action.

Qualifications

• 7+ years of software engineering experience with production products
• Hands-on experience implementing LLM-powered features (RAG, tool loops, workflow automation)
• Strong engineering skills across services, APIs, and data flows
• Comfortable coding and collaborating with product & design without formal management titles

Responsibilities

• 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).
• Make pragmatic architecture decisions and de-risk tricky areas.
• Partner with product and design to refine ideas, shape scope, and iterate on end-to-end experiences.
• Collaborate with other engineering teams to integrate with existing systems.
• Write clear, reliable, well-tested code that ships quickly and scales.

Skills

7+ years software eng

LLM-powered features

Ruby on Rails

React

APIs & data flows

Cross‑functional collaboration

Tools

APIs & services

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’ll be 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.

At Gusto, we don't use titles the traditional way, as a signal of rank or hierarchy. Instead, our titles describe two things at once — your craft (what you do, e.g. Engineering, Design) and your scope of ownership (what you're accountable for) — which is why you’ll see something like \"Head of X\" instead of a rank word like \"Director\" that tells you neither. Because of this, the title on this posting may look different from what you'd expect based on the scope and seniority of the role, and from how similar roles are typically titled elsewhere. If you have questions about how this role compares to your current title or level, your recruiter can help translate.

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.

Reliable, consistent presence

We expect regular and predictable attendance, whether you're working in‑office, hybrid, or fully remote, so that you stay closely connected to your team, customers, and stakeholders in real time and ensure colleagues and customers receive the timely support and responsiveness they deserve.

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.