Staff Software Engineer, Business Insurance

Triwill Group; New York (NY); Hybrid; USD 197,000 - 247,000; Full time

Benefits offered by this job

Equity (RSUs)

Remote-friendly roles

Job summary

Gusto is building the next generation of the business insurance purchase experience. You will take projects from design through implementation to launch, shipping AI-powered features that simplify how businesses discover, evaluate, and purchase insurance.

You will work with a growing team to deliver reliable, end-to-end experiences and mentor engineers along the way. Join a fast-growing unit focused on innovative AI-driven insurance solutions, with opportunities to impact workflows, data flows,

Qualifications

• 8+ years of software development experience.
• AI-native mindset with AI tools embedded in daily workflow.
• Impact-driven with end-to-end multi-quarter delivery experience.

Responsibilities

• Design, build, and test core Business Insurance products that are reliable and scalable.
• Design and implement AI-powered Business Insurance experiences.
• Iterate quickly based on feedback and metrics once features are live.
• Partner with product, design and XF partners to refine ideas and scope.
• Mentor and develop engineers on the team with code reviews and knowledge sharing.

Skills

AI mindset

End-to-end delivery

Communication skills

Ruby on Rails

Python

Platform APIs

Tools

Rails tooling

Observability

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 part of the team building the next generation of the business insurance purchase experience at Gusto. This role is built for someone who wants to be part of a fast-growing team and build products that customers like to use. You'll take projects from design through implementation to launch, working closely with a good size team to ship AI-powered features that simplify and modernize how businesses discover, evaluate, and purchase insurance. If you're excited about joining a team early in its growth, executing reliably on shipping products rapidly, and learning by building alongside experienced engineers, you'll thrive here.

About the Team

Business Insurance is one of Gusto's fastest-growing areas. We own the end-to-end business insurance experience — both on and off the Gusto platform — spanning the sale and servicing of P&C insurance products such as Workers' Compensation and General Liability, as well as PEO. The domain is inherently complex, and that complexity creates real opportunity: to rethink how small business owners experience insurance through innovative AI and thoughtful system design, moving the industry beyond its traditional constraints and delivering something meaningfully better for our customers.

Here’s what you’ll do day-to-day

• Design, build, and test core Business Insurance products that are reliable and scalable
• Design and implement innovative AI-powered Business Insurance experiences
• Iterate quickly based on feedback and metrics once features are live.
• Partner with product, design and XF partners to refine ideas, shape scope, and iterate quickly on end-to-end experiences.
• Mentor and develop engineers on your team. Track record of elevating team capabilities through pairing, code review, and knowledge sharing.

Here’s what we're looking for

• 8+ years of software development experience, 2+ years of doing customer facing products at scale.
• AI-native mindset with AI tools naturally embedded in your daily workflow.
• Impact-driven with proven end-to-end multi-quarter projects delivery experience, from initial scoping and planning through execution, stakeholder management, and successful launch.
• Genuine excitement about joining a fast-growing and high velocity team.
• Natural aptitude for bringing clarity and simplicity to complex, ambiguous problems.
• Strong documentation and communication skills, with the ability to clearly articulate technical tradeoffs and align solutions with business needs across both technical and non-technical audiences.
• Strong Platform and Application Engineering experience (e.g., services, APIs, data flows, observability)
• Strong hands‑on experience building, deploying and evaluating AI solutions in production environments is a plus
• Experience with Ruby on Rails and Python is a plus.

Please note that a two day travel to a Gusto office for onboarding is required for this position.

Our cash compensation amount for this role is targeted at $163,000–$204,000 in Denver & most remote locations, and $197,000–$247,000 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.