Onboarding & Cross-Sell Advocate — Payroll & Compliance

Jobtailor; Arizona; On-site; USD 42,000 - 62,000; Full time

Job summary

Jobtailor is seeking a customer service professional to support small business owners through onboarding and payroll setup. You will manage the ticket queue, promote plan upgrades, and identify cross-sell opportunities for health insurance, workers' comp, and 401(k).

You will diagnose tax discrepancies and work with state portals in real-time. You will collaborate with risk, learn payroll tax rules, and leverage AI tools to streamline workflows, while delivering consultative, outcome-focused

Qualifications

• 1+ years in a high-volume sales or customer service role involving cross-selling, upselling, or quota/KPIs.
• New graduates are welcome; internship or prior work experience should be translated to the role.
• Willingness and ability to learn tax codes, compliance rules, and payroll.
• Customer-focused consultative selling approach
• Goal-oriented and competitive
• Strong communication across phone, email, and chat
• Adaptability and problem-solving ability
• Proven day-to-day experience integrating AI into writing, research, preparation, and summarization
• Track record of providing useful feedback to improve AI tools and processes

Responsibilities

• Handle high-volume phone and email interactions with small business owners from onboarding through running their first payroll.
• Own and manage the ticket queue.
• Position plan upgrades and identify cross-sell opportunities for Health Insurance, Workers' Comp, and 401(k).
• Diagnose tax discrepancies and troubleshoot unfamiliar state portals in real time.
• Make compliance decisions based on state, company size, and industry.
• Configure sick time, PTO, and overtime policies.
• Determine when issues require specialist support and initiate handoffs.
• Collaborate with the Risk team and request additional customer information when needed.
• Use assigned AI tools daily, identify workflow friction and inefficiencies, and provide feedback to shape future tools

Skills

High-Volume Customer Service

Cross-Selling

Tax Code Knowledge

AI Tool Integration

Compliance Decision-Making

Tools

AI Tools

State Portals

Job description

Jobtailor is seeking a customer service professional to support small business owners through onboarding and payroll setup. You will manage the ticket queue, promote plan upgrades, and identify cross-sell opportunities for health insurance, workers' comp, and 401(k).

You will diagnose tax discrepancies and work with state portals in real-time. You will collaborate with risk, learn payroll tax rules, and leverage AI tools to streamline workflows, while delivering consultative, outcome-focused