Senior Health Insurance Sales Operations Analyst

At Gusto, we're on a mission to grow the small business economy.

This is your chance to shape the foundation of a fast-growing, high-impact part of Gusto's business as a Senior Sales Operations Analyst supporting our Health Insurance (HI) Sales team.

About the Role You'll build the insights and AI-powered solutions that make a large, high-volume sales organization, supporting 80+ reps across two segments.

Responsibilities

• Analytics, Reporting & Forecasting:
• Build, automate, and maintain reports and dashboards that track sales performance, funnel metrics, pipeline health, SLAs, and rep productivity.
• Partner with RevOps, Finance, Marketing, and Analytics to produce operational reporting, revenue insights, and forecasting models.
• Own metric definitions and data accuracy so leaders trust the numbers they act on.

• Drive AI Strategy for Sales:
• Identify and prototype AI and automation tools that remove manual friction from the sales process.
• Partner with Sales, BizTech, Product, and Enablement to embed AI into daily sales workflows.
• Source and lead net-new AI and automation projects.

• Process Design & Continuous Improvement:
• Examine workflows and rep performance to identify bottlenecks and recommend process changes.
• Partner with Sales Enablement to document processes and drive adoption of new tools and workflows.

• Operational Support & Problem-Solving:
• Provide day-to-day support to HI Sales leadership and reps.
• Own account and territory administration as the business evolves.
• Troubleshoot reporting issues, broken workflows, and gaps in pipeline visibility.

• Cross-Functional Partnership & Communication:
• Work closely with Sales Leadership, RevOps, Finance, BizTech, and Product to keep everyone aligned.
• Translate sales challenges into clear business requirements and partner cross-functionally to design solutions.

Requirements

• 5+ years in Sales Ops, RevOps, or a similar analytical GTM role.
• Strong Salesforce proficiency.
• Analytical depth across Salesforce reports and dashboards, SQL, Tableau or Looker, and Excel/Google Sheets.
• Hands-on experience with forecasting, pipeline management, and territory or quota planning.
• Comfort evaluating AI and automation tools and prototyping simple workflows.
• Excellent written and verbal communication.
• A first-principles problem solver who breaks down ambiguous issues and builds structured solutions.
• Exceptionally organized and detail-oriented.

Preferred Qualifications

• Experience in payroll, HR tech, or SMB SaaS go-to-market motions.
• Experience supporting a regulated or compliance-driven sales segment such as health insurance or benefits.
• Experience designing or implementing automations, AI workflows, or similar tooling.
• A track record of building cross-functional relationships across Sales, BizTech, and Analytics.

What We Offer

• Competitive base pay, benefits, and equity (RSUs).
• Cash compensation amount for this role is $104,490/yr to $128,000/yr in Denver & Scottsdale and $127,430/yr to $155,000/yr for San Francisco & New York.