Jr. Onboarding Associate

About the Role:

Your role will be to help small business customers choose Gusto. Interacting with customers who sign up on our website via email, chat, and live phone interactions, you’ll help match our people platform offering to their specific business needs, exercising advisory sales skills. You’ll help them navigate an important onboarding process, demonstrating sophisticated customer success skills.

Our team of over a hundred sales professionals includes folks practices across all channels and with different types of customers, but we all share deep passion and commitment to solutions selling: our company exists to solve problems for small businesses, and our sales team is a vital front door for small businesses who need and love our solutions. We have communal goals, a team spirit, and company leadership that cares about selling the right way.

Here’s what you’ll do day-to-day:

• Customer conversations: Handle high-volume inbound interactions across phone, chat, and email with small business owners at every stage — discovery, decision, and onboarding
• Drive outcomes: Treat every touchpoint as a chance to move customers forward, from onboarding milestones to their first payroll run
• Grow revenue: Proactively position plan upgrades and surface cross-sell opportunities for Health Insurance, Workers' Comp, and 401(k)
• Advisory selling: Build consultative selling skills tailored to small business needs
• Product mastery: Develop deep product expertise and genuine customer empathy over time
• Growth & community: Participate in career development and community opportunities at Gusto
• Use AI-powered workflows as a core part of how you sell: running assigned tools daily, surfacing friction and inefficiencies as you find them, and collaborating with your team to influence what gets built or improved 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
• Customer focus: A genuine commitment to empathy and ethical business practices
• Drive: Motivation to hit your goals and continuously sharpen your craft
• Communication: Strong skills across phone, email, and chat
• Adaptability: You thrive on challenge and adjust quickly when things shift
• AI: Proven, day-to-day experience integrating AI into how you work — across writing, research, prep, and summarization as a core part of your workflow, with a track record of giving clear, useful