Sales Onboarding Advocate

Start free →

Or apply yourself on the official page →

About the role

About Gusto At Gusto, we're on a mission to grow the small business economy. We handle the hard stuff — payroll, health insurance, 401(k)s, and HR — so owners can focus on their craft and their customers. With teams in Denver, San Francisco, and New York, we support more than 500,000 small businesses nationwide and are building a workplace that reflects the people we serve. All full-time employees receive competitive base pay, benefits, and equity (RSUs) — because everyone who helps build Gusto should share in its success. Offer amounts are determined by role, level, and location. Learn more about our Total Rewards philosophy . AI is a fundamental part of how work gets done at Gusto. We expect all team members to actively engage with AI tools relevant to their role and grow their fluency as the technology evolves. AI experience requirements vary by role and will be assessed during the interview process. About the Role: This role blends technical problem-solving with sales and customer service. After training, you'll be helping small business owners get their payroll and HR set up correctly. This means entering their past information, catching mistakes in their setup before they cause problems, and helping them navigate state and federal tax guidelines (every state does this differently, so you'll become the expert who can guide customers through all 50). This team is where technical sales careers start at Gusto. You'll build a strong foundational understanding of payroll, tax, and compliance expertise while developing consultative sales skills, and that opens doors. Reps who excel here can grow into specialized roles working in Implementations and Solutions Engineering. If you're looking for a sales career with a technical backbone, this is where that path starts. Here’s what you’ll do day-to-day: • Customer conversations: Handle high-volume customer interactions across phone and email with small business owners guiding them from onboarding to running their first payroll. • Pipeline management: Own your ticket queue the way a seller owns their opportunity pipeline. • Grow revenue: Proactively position plan upgrades and surface cross-sell opportunities for Health Insurance, Workers' Comp, and 401(k). • Technical diagnosis: Catch tax discrepancies live, troubleshoot unfamiliar state portals in real time, and make the right compliance call for each state, size, and industry combination. • Compliance setup: Configure sick time, PTO, and overtime policies to keep companies compliant from day one • Work across teams: You'll know when a customer's situation is something you can solve yourself versus when it needs a specialist, and you'll get that handoff started. You'll also work closely with our Risk team, asking customers for extra information when needed to build trust. • AI-powered workflows: Use assigned AI tools daily as a core part of how you work, surfacing friction and inefficiencies and giving feedback that shapes what gets built next. Here’s what we're looking for: • Experience: 1+ years in a high-volume sales or customer service role where you were cross-selling, upselling, or hitting a quota/KPIs. We love to hire new grads too, so if that’s you, please be prepared to translate how your internship or prior work experience would translate to this type of role. • Eager to learn: You're excited to dive into a brand new industry and figure out the details, whether that's tax codes, compliance rules, or how payroll actually works behind the scenes. • Customer obsessed: You put customer needs first, listening closely to understand what they would benefit from and help them understand how different parts of our product will affect their business. You build trust through consultative conversations, and that trust is

View the official posting →