Senior Health Insurance Sales Operations Analyst

Gusto•San Francisco, NY

1d•Hybrid

About The Position

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.

Requirements

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.

Nice To Haves

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.

Responsibilities

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.
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.
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, 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.
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.