Strategic Operations Lead
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.
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
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