Principal Software Engineer

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At Gusto, we’re on a mission to grow the small business economy. We handle the hard stuff—like payroll, health insurance, 401(k) s, and HR—so owners can focus on their craft and customers. With teams in Denver, San Francisco, and New York, we’re proud to support more than 400,000 small businesses across the country, and we’re building a workplace that represents and celebrates the customers we serve.

As Gusto transitions to an AI‑native company, this role will help shape how intelligence is embedded across our Growth platform — from acquisition to onboarding to expansion. You’ll lead engineering efforts that make our systems adaptive, data‑driven, and intelligent by design.

Building not only for scale and reliability, but for learning and continuous optimization where every part of the funnel can reason, predict, and personalize. You’ll operate at the intersection of Growth systems, AI capabilities, and platform evolution to help unlock Gusto’s next phase of sustainable revenue growth.

We’re accelerating Gusto’s revenue growth by providing
1) an acquisition platform for driving visitors and leads,
2) an onboarding platform for converting leads to customers, and
3) upsell systems for expansion efforts. We’re also in an exciting phase of rebuilding our Revenue Systems stack, which will be key in unlocking Gusto’s next phase of growth.

Our focus is shifting from deterministic user journeys to intelligent growth systems — ones that understand intent, tailor experiences, and continuously improve through data and feedback.

We’re looking for a strategic and motivated engineering leader to empower and scale the engineering teams that are building Gusto’s next big thing!

• Define, iterate, and execute on initiatives contributing to Growth’s technical roadmap to drive revenue growth.
• Champion AI‑native patterns in Growth systems — designing for learning loops, feedback‑driven iteration, and safe model usage in customer‑facing contexts.
• Help establish best practices for experimentation, evaluation, and observability in AI‑augmented Growth experiences.
• Partner with cross‑functional teams to tackle complex and ambiguous problems, translating them into engineering solutions that drive our customer acquisition and ACV expansion platform forward.
• Collaborate with AI platform and data science teams to integrate model‑driven insights into Growth workflows — such as lead scoring, onboarding personalization, intelligent upsell recommendations, and AI/ML‑driven comms platform.
• Execute in different horizons based on Growth’s overall goals. This means at times, embedding in a team for multiple months/quarters to deliver complex projects, and at other times, kicking off ambiguous initiatives and helping teams drive alignment and build momentum.
• Execute in different capacities based on the needs of the org and initiative. Dive deep into the hardest technical areas while delegating the rest to partnering teams.
• Engage with all development teams across Gusto to align and drive towards long‑term maintainability and stability of our systems.
• Mentor and provide guidance to software engineers, fostering growth and development.
• Actively participate in code reviews and maintain code quality.

• 12+ years of professional software development experience.
• Curiosity and ability to operate in an AI‑native environment — integrating intelligence, automation, and experimentation into how we grow the business.
• Hands‑on experience building large‑scale, complex systems in a wide range of domains.
• Web architecture expertise, including observability and performance.
• Experience in highly cross‑functional environments for highly complex products.
• Experience as tech lead, overseeing large initiatives across multiple teams.
• Experience in scaling Engineering organizations.
• Nice to have:
  • Experience designing or implementing product experiences incorporating ML and AI — from recommendations to intelligent onboarding or personalization systems.
  • Experience building complex revenue systems that span multiple…