Health Insurance Sales Operations Analyst at Gusto

Senior Health Insurance Sales Operations Analyst

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.

Here's what you'll do day-to-day:

Analytics, Reporting & Forecasting

• 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 RevOps, Finance, Marketing, and Analytics to produce operational reporting, revenue insights, and forecasting models across the weekly forecast, monthly reviews, and QBR cadence.
• 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, such as content generation, analytics copilots, and call coaching, that remove manual friction from the sales process.
• Partner with Sales, BizTech, 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.

Process Design & Continuous Improvement

• 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.

Operational Support & Problem-Solving

• 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, and coverage planning, plus monthly sales-compensation reconciliation.
• Troubleshoot reporting issues, broken workflows, missing CRM data, and gaps in pipeline visibility with fast, accurate fixes.

Cross-Functional Partnership & Communication

• Work closely with Sales Leadership, RevOps, Finance, BizTech, and Product to keep everyone aligned and remove obstacles to progress.
• Translate sales challenges into clear business requirements; partner cross-functionally to design solutions and durable improvements.
• Keep stakeholders aligned with clear, regular updates to managers and senior leadership on timelines, risks, and outcomes.
• Act as a trusted advisor, bringing structure, insight, and clarity to complex or ambiguous problems.

Here's what we're looking for:

• 5+ years in Sales Ops, RevOps, or a similar analytical GTM role; ideally in a fast-paced SaaS or fintech environment.
• Strong Salesforce proficiency; you can spot data issues, audit pipeline problems, manage account ownership and routing, and build reports and dashboards that reps and leaders actually use.
• 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 on a recurring cadence; for example, a weekly forecast feeding monthly reviews and QBRs.
• Comfort evaluating AI and automation tools and prototyping simple workflows to improve productivity.
• Excellent written and verbal communication; you simplify complex information and create alignment from frontline reps to senior directors.
• A first-principles problem solver who breaks down ambiguous issues, tests hypotheses, and builds structured solutions.
• Exceptionally organized and detail-oriented, you manage multiple projects and recurring workflows while protecting data quality and operational reliability.
• A strong partner to sales, with a track record supporting teams that have competing, fast-changing priorities.

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.
• Experience building systems to support new or evolving sales motions, with comfort in fast iteration and testing in live sales environments.