Senior Staff Software Engineer, Benefits

Gusto • San Francisco, CA; Denver, CO; New York, NY; Los Angeles, CA; Seattle, WA; Toronto, Ontario, CAN • 2d ago

About the Role

As a Senior Staff Software Engineer on the Benefits Advisory team, you will spearhead the architectural evolution of Gusto’s benefits growth as we transition to an AI-native company. This is a full-stack architecture role where you will be instrumental in designing and building the foundational platform that enables customers to explore, apply for, and maintain their benefits.

Your work will focus on transforming our benefits opportunity, shopping and renewal flows, creating clear system boundaries that enable efficient reuse and increased scalability, allowing the ability to offer a wider variety of products more quickly. You will design services that continue to scale the organization while enabling novel AI-driven interfaces to deliver a delightful benefits shopping experience.

You’ll operate at the intersection of marketing, sales, and engineering. If you are passionate about building highly scalable systems that can reason, predict, and personalize to unlock Gusto Benefits’ next phase of sustainable growth, we’d love to have you join our team.

About the Team

The Benefits Advisory team is building the next generation of infrastructure that powers benefits applications, making it easier than ever to give customers access to the absolute best benefits for their needs.

Our mission is to build a robust system that informs our customers of the most relevant benefits options, making it easier than ever to confidently fulfill benefits that fit our customers current and future neds.. We’re building a world-class technology platform designed to understand customer context in real-time, and continuously improve through data and feedback. This means rapid experimentation, fast learning, and strong cross-functional partnership.

We prioritize quality, observability, and uptime because these intelligent systems are fundamental to Gusto's growth and brand. We partner closely with Marketing, Sales, and Operations to build and connect the AI-powered tools they use every day.

Here’s what we're looking for:

Architect and evolve our customer-facing web platforms with a focus on scale, performance, and AI-driven personalization
Design, build, and maintain shared services to enable rapid iteration on product offerings
Implement and optimize key workflows for a best-in-class customer experience.
Write high-quality, well-tested code across the stack, leveraging AI-powered tools to accelerate development and improve reliability
Support, mentor, and up-level fellow engineers on the team, helping to establish best practices for AI-native design patterns.
Partner cross-functionally with Marketing, Sales, Operations and leadership to translate business needs into technical solutions that fit our needs now and in the future.
Be an owner of the long-term technical roadmap, ensuring it aligns with Gusto’s AI-native strategy

Here’s what we're looking for:

12+ years of experience building scalable and robust web applications
Curiosity and ability to operate in an AI-native environment. Integrating intelligence, automation, and experimentation into systems.
Deep experience building modern and accessible frontend applications with technologies such as React, TypeScript, and Next.js.
Deep experience with backend API development, data modeling and database design
Deep experience in CI/CD and observability.
Ability to act as a thought partner for both technical (Engineering, AI/Data) and business (Sales, Operations) teams.
A balance of pragmatic execution and long-term architectural thinking to build a scalable, intelligent platform.
Experience enabling productivity across large engineering organizations.
Nice to have:
- Hands-on experience designing or implementing product experiences incorporating ML/AI, such as AI-driven personalization engines, recommendation systems, or predictive intent models.
- Experience with generative AI or LLMs, particularly in applications related to content personalization (for a CMS) or building intelligent customer-facing agents.
- Familiarity with building in React and Ruby on Rails

Compensation

Our cash compensation amount for this role is targeted at $225,000 - $275,000 for San Francisco, New York, and Seattle, $205,000- $255,000 in Los Angeles, $185,000 - $235,000 in Denver, and $200,000 - $250,000 CAD for Toronto, Canada. 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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