Senior Staff Software Engineer, Benefits

Gusto; New York (NY); Hybrid; USD 191,000 - 265,000; Full time

Benefits offered by this job

Equity (RSUs)

Job summary

Gusto is seeking a Staff Software Engineer on the Benefits Advisory team to architect and build scalable, AI‑driven benefits experiences. You will transform benefits flows and design services enabling rapid product iteration and personalized customer experiences.

You will collaborate across Marketing, Sales, Operations and Engineering to deliver reliable, scalable infrastructure and AI‑powered interfaces supporting growth and a best‑in‑class shopping experience.

Qualifications

• 8+ years of experience building scalable full‑stack web applications.
• Frontend: React and TypeScript.
• Backend: API development, data modeling, database schema design.
• Experience building AI interfaces and AI‑driven personalization patterns.
• Deep experience with CI/CD and observability best practices.
• Ability to partner with technical and business teams.
• Nice to have: Ruby on Rails familiarity; experience with recommendation systems; AI architecture for scalable services.

Responsibilities

• Architect and evolve customer‑facing web platforms with a focus on scale and performance.
• Design, build, and maintain shared services for rapid product iteration.
• Implement and optimize key workflows for a best-in-class customer experience.
• Write high‑quality, well‑tested code across the stack with AI‑assisted tooling.
• Mentor fellow engineers and promote AI‑native design patterns.
• Partner with Marketing, Sales, Operations and leadership to translate business needs into technical solutions.
• Influence the technical roadmap to align with AI‑native strategy.

Skills

Full-stack development

React

TypeScript

API development

Data modeling

CI/CD

Observability

AI interfaces

Tools

Ruby on Rails

AI tooling

Job description

About the company

At the company, 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 the company 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 the company. 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

As a Staff Software Engineer on the Benefits Advisory team, you will be directly accountable for key architectural improvements to the company's benefits platform. This is a full-stack role where you will design and build platform capabilities that enable customers to explore, apply for, and maintain their benefits within your product area.

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, with an emphasis on enabling novel AI-driven interfaces to deliver a delightful benefits shopping experience.

You’ll operate at the intersection of marketing, sales, operations and engineering. If you are passionate about building highly scalable systems that can reason, predict, and personalize to unlock the company 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 needs. 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 the company'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 you’ll do day-to-day:

• Architect and evolve our customer-facing web platforms with a focus on scale and performance

Build innovative AI interfaces to best assist our customers

• 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.
• Influence the technical roadmap for your area of the Benefits Advisory platform, ensuring your work aligns with the company's AI-native strategy and team goals

Here’s what we’re looking for:

• 8+ years of experience building scalable full-stack web applications with expertise in both frontend (React, TypeScript) and backend (API development, data modeling, database schema design)
• Extensive Experience building AI interfaces, iterating on prompts and maintaining high quality evals
• Extensive Experience applying AI tools to accelerate full-stack development, improve code quality, and build intelligent user experiences. Familiar with AI-driven personalization patterns and willing to experiment with AI techniques to improve the benefits shopping experience
• Deep experience in CI/CD and observability best practices.
• 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:
• Direct familiarity with React, Ruby on Rails
• Experience with robust recommendation systems
• AI architecture and scalability for reliable platform services

Compensation

Our cash compensation amount for this role is targeted at $191,000/yr to $225,000/yr in Denver & most remote locations, and $225,000/yr to $265,000/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.

the company 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, the company'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 the company 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 the company.

the company 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. the company considers qualified applicants with criminal histories, consistent with applicable federal, state and local law. the company is also committed to providing reasonable accommodations for qualified individuals with disabilities and disabled veterans i