Top Tech Jobs & Startup Jobs

Design, build, and harden asynchronous infrastructure and developer tooling to improve engineer productivity. Work on background jobs and async communication using Sidekiq, Kafka, and Karafka, collaborate with product engineers, and apply AI/LLMs for large-scale code migrations and faster incident resolution.

Lead product design for Gusto Retirement: define strategy, prototype and ship high-trust, regulated financial experiences, partner with Product/Engineering/Data, use AI-accelerated workflows, evolve design systems, and mentor designers to improve adoption, retention, and cross-product cohesion.

Design, build, and ship production LLM-powered features for Gusto Retirement. Implement and integrate LLMs (RAG, agents, prompting, tool loops), make pragmatic architecture decisions, collaborate with product, design, and engineering, write reliable well-tested code, and drive end-to-end execution and iteration.

Lead and deliver vulnerability management and security operations programs across security, AIT, R&D, infrastructure, and GRC. Define strategy, run prioritization, expand detection and remediation coverage, build AI-driven security workflows and dashboards, manage vendors, budgets, audits, and stakeholder communications to harden the SDLC and scale security for an AI-native company.

Lead Gusto's AI/ML strategy, managing teams in Machine Learning Engineering, AI, and Risk Data Science. Ensure systems are reliable and impactful while fostering a culture of technical excellence.

Serve as the primary, consultative point of contact for retirement benefits clients via phone, email, and Zoom. Provide expert support on 401(k) and plan health, proactively identify churn risk, educate customers on fiduciary responsibilities, leverage AI tools and cross-functional partners to resolve issues, and drive customer retention and engagement.

Own the end-to-end onboarding journey for benefits integrations: drive consultative outreach, manage project timelines, confirm eligibility and compliance, gather required information, build policies, manage enrollments, coordinate with internal and external partners, and ensure accurate, timely benefits implementation and excellent customer experience.

Own inbound customer inquiries via phone (with email/chat flexibility), research complex benefits questions, collaborate cross-functionally to influence product, meet quality/productivity standards, and support peak-season overtime and blackout PTO periods.

Lead financial services compliance for consumer and commercial products, payments, and embedded finance. Advise Product, Engineering, Legal, and Ops on launches, partnerships, controls, monitoring, vendor oversight, regulatory change management, and examinations. Build and scale compliance programs using AI-enabled workflows while ensuring human-in-the-loop controls and risk-based decision making.

Lead design and implementation of the Tax platform: build scalable, fault-tolerant systems, improve extensibility, mentor engineers, drive technical strategy and roadmap, collaborate cross-functionally, improve reliability/incident response, and build AI guardrails to safely leverage agentic LLMs for tax compliance.