Senior Health Insurance Sales Operations Analyst

About Gusto

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 at Gusto. We 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.

About the Role

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.

About the Team

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.

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.

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Our cash compensation amount for this role is $104,490/yr to $128,000/yr in Denver & Scottsdale and $127,430/yr to $155,000/yr for San Francisco & New York. Final offer amounts are determined by multiple factors including candidate location, experience and expertise, and may vary from the amounts listed above.

Gusto has physical office spaces in Denver, San Francisco, and New York City. Employees who are based in those locations will be expected to work from the office on designated days approximately 2-3 days per week (or more depending on role). The same office expectations apply to all Symmetry roles, Gusto's subsidiary, whose physical office is in Scottsdale.

Note: The San Francisco office expectations encompass both the San Francisco and San Jose metro areas. 

When approved to work from a location other than a Gusto office, a secure, reliable, and consistent internet connection is required. This includes non-office days for hybrid employees.

Our customers come from all walks of life and so do we. We hire great people from a wide variety of backgrounds, not just because it's the right thing to do, but because it makes our company stronger. If you share our values and our enthusiasm for small businesses, you will find a home at Gusto. 

Gusto is proud to be an equal opportunity employer. We do not discriminate in hiring or any employment decision based on race, color, religion, national origin, age, sex (including pregnancy, childbirth, or related medical conditions), marital status, ancestry, physical or mental disability, genetic information, veteran status, gender identity or expression, sexual orientation, or other applicable legally protected characteristic. Gusto considers qualified applicants with criminal histories, consistent with applicable federal, state and local law. Gusto is also committed to providing reasonable accommodations for qualified individuals with disabilities and disabled veterans in our job application procedures. We want to see our candidates perform to the best of their ability. If you require a medical or religious accommodation at any time throughout your candidate journey, please fill out this form and a member of our team will get in touch with you.

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