Health Insurance Sales Operations Analyst

Gusto is hiring a Senior Sales Operations Analyst to support its Health Insurance Sales team. The role builds analytics, reporting, forecasting, and AI-powered solutions while improving sales processes, territory administration, and cross-functional execution.

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

Preferred

ideally in a fast-paced SaaS or fintech environment

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

SaaS Experience

Fintech Experience

Payroll Experience

HR Tech Experience

SMB SaaS Go-to-Market

Regulated Sales Experience

Compliance-Driven Sales

Health Insurance Experience

Employee Benefits Experience

Automation Design

AI Workflow Design

Sales Systems Building

Sales Motion Development

Live Sales Testing

Cross-Functional Relationship Building

Iterative Testing

Benefits

All full-time employees receive equity (RSUs).

Employees based in Denver, San Francisco, New York City, and Scottsdale are expected to work from the office approximately 2-3 days per week (or more depending on role).

Company

Payroll, HR, benefits, and compliance software for small businesses

San Francisco, California, USA

https://www.gusto.com/

Founded in 2011

1001-5000 employees

Qualifications

5+ years in Sales Ops, RevOps, or a similar analytical GTM role

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

Ideally in a fast-paced SaaS or fintech environment

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

5+ years in Sales Ops, RevOps, or a similar analytical GTM role;

Required skills

Sales Operations, Salesforce, SQL, Tableau, Looker, Excel, Google Sheets, Sales Forecasting, Pipeline Management, Territory and Quota Planning, SaaS Go-to-Market

Preferred skills

ideally in a fast-paced SaaS or fintech environment

Experience

5+ years