About Gusto

Mission: Grow the small business economy by handling payroll, health insurance, 401(k)s, and HR.
Locations: Denver, San Francisco, New York.
Supports over 400,000 small businesses nationwide.

About the Team

Integrated Benefits (IB) team is part of Gusto’s Benefits organization.
Manages complex platform areas including Voluntary Life and Disability (vLiDi) products.
Works with interconnected systems, external integrations, and regulated domains.
Plays a key role in modernizing platform foundations and enabling AI-native systems.

About the Role

Position: Senior Staff Software Engineer on the Integrated Benefits team.
Responsibilities:
Own and evolve architecture of key areas in the Integrated Benefits platform.
Drive architectural improvements for scalability, extensibility, and resilience.
Influence architectural decisions and technical strategy within domain.
Partner across teams to align technical direction.
Guide systems through complex transitions.
Operate with high autonomy and scope.
Balance immediate delivery with long-term platform health.

What You’ll Do

Own and evolve architecture ensuring scalability, reliability, adaptability.
Drive architectural decisions balancing business goals and technical constraints.
Contribute to technical roadmap aligned with team objectives and Benefits engineering priorities.
Design/build shared platform capabilities supporting vLiDi products and broker integrations.
Lead technical approach to complex problems; partner with product/design/cross-functional teams.
Identify cross-team dependencies; influence alignment on architectural patterns and standards.
Mentor engineers through design reviews and architectural guidance.
Apply AI tools to accelerate development, improve code quality, enable intelligent product capabilities; evaluate emerging frameworks using success criteria.
Contribute to shared tooling/patterns/standards enabling safe experimentation including AI-driven workflows.

What We’re Looking For

10+ years software engineering experience building/supporting production software systems.
Significant experience designing/evolving complex backend systems; deep Ruby on Rails experience.
Ability to own architectural decisions within product domain; influence technical direction across teams.
Experience building/contributing to platform capabilities or shared systems used by multiple teams.
Strong foundation in system design, data modeling, working with complex interconnected production systems.
Comfort operating in ambiguous problem spaces; leading technical decision-making through uncertainty.
Strong communication/collaboration skills; ability to influence without formal authority.
Experience applying AI tools in production engineering workflows for development velocity, system quality, or product behavior improvement.
Familiarity evaluating AI-driven outputs using well-defined success criteria and operational constraints.

Nice to Haves

Experience in regulated domains such as Benefits, Payroll, HR, Taxes, Compliance.
Experience designing/evolving large-scale integration platforms or service-oriented architectures.
Prior work supporting external partners or third-party integrations.
Experience contributing to internal developer platforms/shared tooling/technical standards.
Exposure to AI-driven systems beyond experimentation including monitoring/evaluation/governance.

Compensation

Target cash compensation: $223,000 to $265,000 per year (San Francisco & New York).
Stock equity is additional.

Location & Work Expectations

Offices in Denver, San Francisco (including San Jose metro), New York City; hybrid work model expected ~2 days/week onsite (or more depending on role).
Secure/reliable internet required when working remotely.

Equal Opportunity Statement

Gusto is an equal opportunity employer committed to diversity and inclusion. They provide reasonable accommodations for qualified individuals with disabilities during the application process.