Senior Sales Operations Analyst - Health Insurance

Gusto•Chicago, NY

7d•Hybrid

About The Position

This is your opportunity to shape the foundation of a rapidly growing, high-impact segment of Gusto's business as a Senior Sales Operations Analyst supporting our Health Insurance (HI) Sales team. In this role, you will develop insights and AI-powered solutions that enhance productivity for over 80 sales representatives across two segments. You will act as the link between data, processes, and execution, translating real-world sales challenges into tools, reports, automations, and workflows that make a difference. You will contribute to the growth of a business segment that serves tens of thousands of small businesses through smarter, data-driven sales strategies. If you thrive at the intersection of analytics, problem-solving, and supporting others, this role offers you ownership, visibility, and the opportunity to influence how Gusto sells health insurance. The HI Sales Operations team collaborates closely with sales leadership to support two dynamic sales teams that contribute significantly to Gusto's growth. We consider ourselves builders, problem solvers, and strategic partners who transform uncertainty into clarity and fragmented processes into scalable, repeatable systems. Our responsibilities encompass quotas, pipeline health, forecasting, process design, data integrity, go-to-market strategy, and increasingly, AI-driven optimization. Our team values curiosity, open communication, and the commitment to empower over 80 sales representatives to operate efficiently and confidently.

Requirements

You possess a unique blend of analytical sharpness, operational instincts, and strong communication skills.
You can move quickly while paying attention to details and are comfortable supporting a high-volume sales team where priorities can change rapidly.
You thrive on analyzing complex data, resolving workflow issues, and transforming problems into clear solutions.
Most importantly, you communicate effectively with colleagues at all levels, from frontline representatives to directors, ensuring alignment, visibility, and trust.
Experience: 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 know how to identify data issues, audit pipeline problems, and create reports and dashboards that sales reps and leaders actually use.
Analytical Proficiency: Proficient in creating reports and dashboards using Salesforce, Tableau, Looker, Excel, and Google Sheets.
Proficient in AI and Automation: Skilled at evaluating AI tools and automation solutions to identify opportunities for improving productivity.
Experienced in prototyping simple workflows and incorporating AI into operational processes (no engineer-level skills required).
Excellent Communication: Excellent communication skills with the ability to simplify complex information for stakeholders, providing written and verbal updates that align senior leadership with stakeholders.
A first-principles problem solver capable of breaking down ambiguous issues, testing hypotheses, and developing structured solutions.
Exceptionally organized & detail-oriented, capable of managing multiple projects and recurring workflows while ensuring data quality and operational reliability.
A strong partner to sales , able to tackle daily challenges and create solutions that improve their experience and efficiency.
Proven experience supporting teams with competing priorities.

Nice To Haves

Experience in payroll, HR tech, or SMB SaaS go-to-market motions.
Experience designing or implementing automations, AI workflows, or similar tooling.
Track record of building strong cross-functional relationships across Sales, BizTech, and Analytics.
Experience building systems to support new sales motions.
Comfort with fast iteration, experimentation, and testing in live sales environments.

Responsibilities

Analytics, Reporting & Forecasting Develop, automate, and maintain reports and dashboards that track performance, funnel metrics, pipeline health, SLAs, and representative productivity.
Work collaboratively with RevOps, Finance, Marketing, and Analytics teams to generate operational reports, revenue insights, and forecasting models.
Create metrics and dashboards for sales performance to ensure data accuracy, consistent definitions, and clear documentation.
Drive AI Strategy for Sales Actively identify and prototype AI tools (such as content generation, analytics copilots, and call coaching) to eliminate manual friction in the sales process.
Collaborate with Sales, BizTech, Product, and Enablement teams to integrate AI into daily sales activities, improving both efficiency and effectiveness.
Examine existing workflows and rep performance to pinpoint bottlenecks and offer actionable recommendations that link data insights to automation and process enhancements.
Process Design & Continuous Improvement Identify workflow bottlenecks and refine processes and tools to enhance conversion rates, sales efficiency, and customer experience using data insights and feedback.
Collaborate with Sales Enablement to document processes, create playbooks, and ensure that any changes are effectively communicated and embraced by the sales team.
Operational Support & Problem Solving Provide daily support to HI Sales leadership and representatives across the organization by handling ad-hoc data requests, routing inquiries, resolving process issues, managing account assignments, and conducting one-off investigations.
Troubleshoot reporting issues, broken workflows, missing Salesforce data, and gaps in pipeline visibility, providing fast and accurate solutions.
Translate sales challenges into clear business requirements, then collaborate cross-functionally to design solutions or implement long-term improvements.
Cross-Functional Partnership & Communication Work closely with Sales Leadership, RevOps, Finance, BizTech, and Product teams to ensure alignment and remove obstacles to progress.
Manage change effectively by providing regular updates to stakeholders, including managers and senior leadership, on project timelines, challenges, and outcomes with clear communication.
Act as a trusted advisor, providing structure, insights, and clarity to complex or ambiguous issues.