Senior Sales Operations Analyst Health Insurance

About Gusto

At Gusto were on a mission to grow the small business economy. We handle the hard stufflike payroll health insurance 401(k)s and HRso owners can focus on their craft and customers. With teams in Denver San Francisco and New York were proud to support more than 400000 small businesses across the country and were building a workplace that represents and celebrates the customers we serve. Learn more about our Total Rewards philosophy.

About the Role:

This is your opportunity to shape the foundation of a rapidly growing high-impact segment of Gustos business as a Senior Sales Operations Analyst supporting our Health Insurance (HI) Sales 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.

About the Team:

The HI Sales Operations team collaborates closely with sales leadership to support two dynamic sales teams that contribute significantly to Gustos 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.

Heres what youll do day-to-day:

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.

Heres what were looking for:

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.

Preferred Qualifications

• 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.

Our cash compensation amount for this role is $104490 to $128000 for Denver Atlanta & Las Vegas. $126530 to $155000 for San Francisco & New York. $97960 to $120000 for Phoenix. 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 Gustos 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 its 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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