Sales Onboarding Advocate

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

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

Requirements

• 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

Core Competencies

Demonstrates expertise in high-volume customer interactions, compliance decision-making, and consultative selling. Proficient in utilizing AI tools for workflow improvement and problem-solving in payroll and tax-related contexts.

Highest-signal resume keywords

• High-Volume Customer Service
• Cross-Selling
• Tax Code Knowledge
• AI Tool Integration
• Compliance Decision-Making

Hard Skills

• Payroll Management
• Tax Discrepancy Diagnosis
• Policy Configuration
• Quota Achievement
• KPI Tracking

Soft Skills

• Strong Communication
• Adaptability
• Problem-Solving
• Customer-Focused Approach
• Goal-Oriented

Industry Keywords

• Health Insurance
• Workers' Compensation
• 401(k)
• Compliance Rules
• Small Business

Tools & Technologies

• AI Tools
• State Portals