Retirement AI Senior Staff Engineer

Gusto • Denver, CO;San Francisco, CA;New York, NY • 2d ago

Why This Job is Featured on The SaaS Jobs

This Senior Staff Engineer role sits at the intersection of SaaS product engineering and applied AI, focused on shipping language model features directly into a customer-facing retirement product. In the current SaaS landscape, where many teams are still experimenting, the emphasis here is on production delivery, end-to-end ownership, and integrating LLM workflows into an existing product and platform surface.

For a long-term SaaS career, the work builds durable strengths: turning ambiguous product concepts into measurable software, making architecture tradeoffs that hold up under real usage, and establishing the operational habits that AI features require, such as evaluation, monitoring, and iterative improvement. The role also reinforces cross-functional execution with product and design, a core competency for senior engineers in subscription software where iteration and adoption matter as much as initial release.

This role is best suited to an experienced, hands-on builder who prefers high agency and direct accountability over narrow ownership. It fits someone comfortable leading through technical decisions and delivery rather than formal people management, and who enjoys pragmatic collaboration across teams while keeping a clear line of responsibility for outcomes.

The section above is editorial commentary from The SaaS Jobs, provided to help SaaS professionals understand the role in a broader industry context.

Job Description

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:

10+ 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).

Please note that travel to Gusto’s Denver office for onboarding is required for this position. If you have any questions regarding this requirement, please share with your recruiter.

Our cash compensation amount for this role is targeted at $213,000/yr to $236,000/yr in Denver & most remote locations, and $251,000/yr to $278,000/yr for San Francisco, Seattle & 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.

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