Senior Sales Operations Analyst - Business Insurance

Senior Sales Operations Analyst – Business Insurance

Join to apply for the Senior Sales Operations Analyst – Business Insurance role at Gusto

At Gusto, we’re on a mission to grow the small business economy. We handle the hard stuff—like payroll, health insurance, 401(k) s, and HR—so owners can focus on their craft and customers. With teams in Denver, San Francisco, and New York, we pride ourselves on supporting more than 400,000 small businesses across the country and building a workplace that represents and celebrates the customers we serve.

Gusto’s Benefits Sales team is launching a new Business Insurance (BI) vertical, a rapidly growing segment poised to scale quickly. You will be the primary Sales Operations thought partner for this new vertical, designing, implementing, and optimizing processes, and creating reports to track performance.

The Revenue Operations team supports the Benefits Sales organization and collaborates closely with sales leadership to empower a fast‑paced sales team that drives one of Gusto’s key growth areas. The team works on quotas, pipeline health, forecasting, process design, data integrity, and go‑to‑market strategy with an increasing emphasis on AI‑driven optimization.

• Process & Systems Optimization
  • Design and implement the BI Sales engine: lead the creation and deployment of AI‑driven workflows that automate manual processes and boost sales productivity.
  • Create a scalable system for tracking quotas, assigning territories, and modeling commissions, capable of expanding from 2 representatives to 60 within a year.
• Analytics & Insights
  • Build and automate dashboards in Salesforce to monitor lead conversion, analyze funnel performance, and identify trends and opportunities for AI use cases.
  • Provide clear, actionable recommendations that link data insights to automation or process improvements.
• AI & Workflow Innovation
  • Identify and prototype AI tools (e.g., content generation, analytics copilots, call coaching) to eliminate manual friction in the sales process.
  • Examine existing workflows and representative performance to pinpoint bottlenecks and offer actionable recommendations that link data insights to automation and process enhancements.
• Cross‑Functional Partnership
  • Act as a trusted advisor to the Head of Sales, Enablement, Finance, Analytics, and Biz Tech to facilitate progress, guide change management, and drive adoption.
  • Identify and address risks, uncertainties, and opportunities to enhance how AI and automation drive business outcomes.
  • Facilitate go‑to‑market readiness for new processes, AI workflows, and product updates by creating documentation and operational requirements.

• 5+ years in Sales Ops, Rev Ops, or a similar analytical GTM role, ideally in a fast‑paced SaaS or Fintech environment.
• High proficiency in Salesforce: identify data issues, audit pipelines, and build reports that leaders actually use.
• 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.
• Builder’s mindset: excel in environments where you build the plane while flying it and transform complex problems into repeatable playbooks.
• Proficient in creating reports and dashboards using Salesforce, Tableau, Looker, Excel, and Google Sheets.
• Proactive learner who looks for the best solution to a problem, whether an AI prototype or a simple process change.
• First‑principles problem solver capable of breaking down ambiguous issues, testing hypotheses, and developing structured solutions.
• Excellent communication skills with the ability to simplify complex information for stakeholders and provide written and verbal updates that align senior leadership.

• 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, Biz Tech, and Analytics.
• Experience building systems to support new sales motions.
• Comf…