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Strategic Operations Lead

99k – 140kDenver, COSan Francisco, CANew York, NYScottsdale, AZHybrid4+ YOE
Summary

Build and operate Benefits Labs, the AI-native system that governs how Gusto tests, validates, and scales operational changes across the Benefits organization. Design agents and workflows to run multiple high-quality pilots in parallel while influencing leadership decisions through evidence-based insights.

About the role

Responsibilities

  • Own the full Benefits Labs lifecycle including intake, pilot design, execution governance, measurement, and leadership recommendations
  • Operate and improve the AI-powered intake system that classifies, routes, and prepares incoming work
  • Run pilot governance ensuring every pilot has defined success metrics, checkpoints, and outputs using AI-driven workflows
  • Pressure-test hypotheses, refine success criteria, and hold Pilot Leads accountable to quality standards
  • Extend the agent and automation architecture across intake routing, workflow execution, evidence synthesis, and readout generation
  • Identify systemic inefficiencies and convert repeatable problems into scalable, AI-powered workflows
  • Develop analytical approaches and produce evidence-based narratives to influence leadership decisions
  • Lead cross-functional coordination across product, engineering, operations, enablement, and business partners
  • Create structure in ambiguous situations and deliver structured readouts, post-mortems, and recommendations
  • Coach Pilot Leads and BizOps partners on AI-powered ways of working

Requirements

  • 4+ years in operations, program management, or business operations in a SaaS, technology, or operationally complex environment
  • Proven ownership of outcomes across complex, cross-functional work
  • AI-native builder: demonstrated experience designing and deploying AI agents, automations, or workflows that execute multi-step work and measuring leverage created
  • Systems thinker who identifies root causes at the process level and builds scalable solutions
  • Strong data fluency with ability to structure problems, define success metrics, and turn data into decision-driving narratives
  • Operator + coach who raises quality of work through feedback, clear standards, and accountability
  • Cross-functional leader with experience driving alignment across product, engineering, and operations without direct authority
  • Comfort with ambiguity and ability to create structure where none exists

Nice-to-Haves

  • Experience in benefits, insurance, or brokerage operations
  • Experience working with operational metrics (cycle time, quality, throughput)
  • Direct experience building or managing AI agents in a production or operational context

Compensation & Benefits

  • Cash compensation: $98,725–$116,000/year in Denver & most major metro locations; $114,285–$140,000/year for San Francisco & New York
  • Equity (RSUs) provided to all full-time employees
  • Competitive benefits package
Skills
AI agentsAI automationWorkflow automationPilot governanceProgram managementCross-functional leadershipData analysisProcess improvementEvidence synthesisStakeholder management
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