Top Tech Jobs & Startup Jobs

Lead Gusto’s approximately 25-person AI Platform engineering organization. Set technical strategy and roadmaps for production AI agents and shared infrastructure, define platform ownership, establish reliability and evaluation standards, develop managers and technical leaders, hire for growth, and align engineering with company-wide AI strategy. Partner closely with product, design, data science, and other engineering teams while advancing AI-native ways of working.

Manage retirement plan conversions by validating asset allocations, reconciling trust and legacy provider data, configuring participant loan records, and ensuring accurate uploads before plan activation. Resolve discrepancies, protect historical data integrity, and collaborate with onboarding, compliance, reconciliations, and client success teams. The role also contributes to automation and tooling improvements while managing competing priorities in a high-volume, deadline-driven environment.

Own and improve Benefits Labs, an AI-powered system for intake, pilot governance, execution, measurement, evidence synthesis, and leadership recommendations. Build agents, automations, and workflows that scale operational change with minimal manual effort. Define success metrics, improve pilot quality, solve systemic process issues, coordinate cross-functional teams, influence decisions through data-driven narratives, coach Pilot Leads, and shape the future operating model for Benefits Labs.

Lead full-stack development of the signup-to-activation experience, inventing and shipping 0-to-1 AI-driven onboarding features across web, messaging channels, and third-party AI assistants. Collaborate with product, design, and data, mentor engineers, scope rapidly, and measure/iterate to improve activation metrics.

Drive expansion revenue within existing customers through high‑velocity outbound and inbound outreach. Make ~60 dials daily, hold consultative calls to uncover upsell/cross-sell opportunities, update Salesforce, hit monthly ARR quota, and use AI-powered workflows to optimize selling and feedback to product teams.

Serve as a trusted HR advisor handling complex employee relations matters: investigations, conflict resolution, performance management, documentation, and risk assessment. Coach managers, partner with Legal and People teams, surface systemic risks, and use data-driven insights to improve fairness and organizational outcomes.

Design, build, test, and launch reliable, scalable business insurance products and AI-powered customer experiences. Partner with product, design, and cross-functional teams to iterate using feedback and metrics. Lead multi-quarter projects from scoping through delivery, communicate technical tradeoffs, and mentor engineers through pairing, code review, and knowledge sharing.

The Senior Staff Security Engineer will lead edge and network security strategies, overseeing design, operation, and incident response for Gusto's security posture, requiring substantial expertise in Cloudflare and AWS.

Architect and scale an internal AI platform and APIs to integrate LLMs into developer workflows. Build autonomous agents, RAG systems, and production-grade tooling to boost developer productivity, ensure reliability, security, and cost-efficiency, and collaborate across product, infrastructure, and security teams.

Lead full‑stack engineering work on tax experiences: design, build, test, and operate scalable systems for tax collection, payment, and filing. Drive technical strategy, mentor engineers, collaborate cross-functionally, prioritize long-term architecture, and apply AI tools to improve developer productivity and customer workflows.