Health Insurance Sales Operations Analyst

Description:

At Gusto, we're on a mission to grow the small business economy. We handle the hard stuff — payroll, health insurance, 401(k) s, and HR — so owners can focus on their craft and their customers. With teams in Denver, San Francisco, and New York, we support more than 500,000 small businesses nationwide and are building a workplace that reflects the people we serve.

All full-time employees receive competitive base pay, benefits, and equity (RSUs) — because everyone who helps build Gusto should share in its success. Offer amounts are determined by role, level, and location. Learn more about our Total Rewards philosophy.

AI is a fundamental part of how work gets done  expect all team members to actively engage with AI tools relevant to their role and grow their fluency as the technology evolves. AI experience requirements vary by role and will be assessed during the interview process.

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. You'll build the insights and AI-powered solutions that make a large, high-volume sales organization, supporting 80+ reps across two segments. You'll sit at the intersection of data, process, and execution; you'll turn real sales challenges into the tools, reports, automations, and workflows that move the numbers.

You'll help grow a business segment that serves tens of thousands of small businesses through smarter, data-driven sales strategies. If you thrive where analytics, problem-solving, and supporting others meet, this role offers ownership, visibility, and the chance to influence how Gusto sells health insurance.

The HI Sales Operations team partners closely with sales leadership to support two dynamic, fast-moving sales teams that contribute meaningfully to Gusto's growth. We think of ourselves as builders, problem solvers, and strategic partners; we turn uncertainty into clarity and fragmented processes into scalable, repeatable systems.

Our work spans quotas, pipeline health, forecasting, process design, data integrity, account and territory administration, go-to-market strategy, and increasingly, AI-driven optimization. We value curiosity, open communication, and a commitment to helping 80+ sales reps operate efficiently and confidently.

• Build, automate, and maintain reports and dashboards that track sales performance, funnel metrics, pipeline health, SLAs, and rep productivity; keep definitions consistent and documentation clear.
• Partner with Rev Ops, Finance, Marketing, and Analytics to produce operational reporting, revenue insights, and forecasting models across the weekly forecast, monthly reviews, and Q  cadence.
• Own metric definitions and data accuracy so leaders trust the numbers they act on.

• Identify and prototype AI and automation tools, such as content generation, analytics copilots, and call coaching, that remove manual friction from the sales process.
• Partner with Sales, Biz Tech, Product, and Enablement to embed AI into daily sales workflows, improving both efficiency and effectiveness.
• Source and lead net-new AI and automation projects, connecting data insights to process improvements that lift rep productivity.

• Examine workflows and rep performance to identify bottlenecks; recommend and implement process and automation changes that improve conversion, efficiency, and the rep experience.
• Partner with Sales Enablement to document processes, build playbooks, and drive adoption of new tools and workflows.

• Provide day-to-day support to HI Sales leadership and reps: ad hoc data requests, process issues, and one-off investigations.
• Own account and territory administration as the business evolves, assignment and coverage upkeep, book reassignments for leave and departures, large-scale account rerouting, and segment reclassification, supported by lead-routing and round-robin automation.
• Support territory, quota,…