Senior Sales Operations Analyst - Health Insurance

About Gusto

At Gusto, we're on a mission to grow the small business economy. We handle the hard stuff—like payroll, health insurance, 401(k) s, and HR—so owners can focus on their craft and customers. With teams in Denver, San Francisco, and New York, we’re proud to support more than 400,000 small businesses across the country, and we’re building a workplace that represents and celebrates the customers we serve.

Learn more about our Total Rewards philosophy.

About The Role

This is your opportunity to shape the foundation of a rapidly growing, high-impact segment of Gusto's business as a Senior Sales Operations Analyst supporting our Health Insurance (HI) Sales team. In this role, you will develop insights and AI-powered solutions that enhance productivity for over 80 sales representatives across two segments. You will act as the link between data, processes, and execution, translating real-world sales challenges into tools, reports, automations, and workflows that make a difference.

You will contribute to the growth of a business segment that serves tens of thousands of small businesses through smarter, data-driven sales strategies. If you thrive at the intersection of analytics, problem-solving, and supporting others, this role offers you ownership, visibility, and the opportunity to influence how Gusto sells health insurance.

About The Team

The HI Sales Operations team collaborates closely with sales leadership to support two dynamic sales teams that contribute significantly to Gusto's growth. We consider ourselves builders, problem solvers, and strategic partners who transform uncertainty into clarity and fragmented processes into scalable, repeatable systems.

Our responsibilities encompass quotas, pipeline health, forecasting, process design, data integrity, go-to-market strategy, and increasingly, AI-driven optimization. Our team values curiosity, open communication, and the commitment to empower over 80 sales representatives to operate efficiently and confidently.

Here’s What You’ll Do Day-to-day

Analytics, Reporting & Forecasting

• Develop, automate, and maintain reports and dashboards that track performance, funnel metrics, pipeline health, SLAs, and representative productivity.
• Work collaboratively with Rev Ops, Finance, Marketing, and Analytics teams to generate operational reports, revenue insights, and forecasting models.
• Create metrics and dashboards for sales performance to ensure data accuracy, consistent definitions, and clear documentation.

Drive AI Strategy for Sales

• Actively identify and prototype AI tools (such as content generation, analytics copilots, and call coaching) to eliminate manual friction in the sales process.
• Collaborate with Sales, Biz Tech, Product, and Enablement teams to integrate AI into daily sales activities, improving both efficiency and effectiveness.
• Examine existing workflows and rep performance to pinpoint bottlenecks and offer actionable recommendations that link data insights to automation and process enhancements.

Process Design & Continuous Improvement

• Identify workflow bottlenecks and refine processes and tools to enhance conversion rates, sales efficiency, and customer experience using data insights and feedback.
• Collaborate with Sales Enablement to document processes, create playbooks, and ensure that any changes are effectively communicated and embraced by the sales team.

Operational Support & Problem Solving

• Provide daily support to HI Sales leadership and representatives across the organization by handling ad-hoc data requests, routing inquiries, resolving process issues, managing account assignments, and conducting one-off investigations.
• Troubleshoot reporting issues, broken workflows, missing Salesforce data, and gaps in pipeline visibility, providing fast and accurate solutions.
• Translate sales challenges into clear business requirements, then collaborate cross-functionally to design solutions or implement long-term improvements.

Cross-Functional Partnership & Communication

• Work closely with Sales Leadership, Rev Ops, Finance, Biz Tech, and Product teams to ensure alignment and remove obstacles to progress.
• Manage change effectively by providing regular…