Benefits Customer Onboarding Manager

Position Overview

Gusto is seeking a customer-obsessed, tactical leader for our Onboarding Advocate (OA) team. As a People Empowerer (PE), you will be a hands-on coach to a pod of Advocates, ensuring your team provides small business owners and their employees with a world-class health insurance onboarding experience. Your primary focus is driving team performance by consistently meeting productivity and quality targets, proactively removing tactical hurdles, and coaching your team to excellence. You will play a critical role in scaling Gusto's benefits business, ensuring our customers have a seamless transition to their new plans. The Onboarding Advocate team is passionate about setting customers up for success with health benefits, managing the complexities of health benefits so that customers can focus on what matters most—their people and their business.

Key Responsibilities

• Drive Operational Excellence: Manage the daily health of your team's funnel, ensuring all customer milestones and SLAs are met with urgency and accuracy.
• Empower & Coach: Provide regular coaching and performance management (via 1:1s and monthly reviews) focused on technical mastery, customer-centricity, and hitting KPIs.
• Remove Roadblocks: Act as the first point of contact for tactical blockers and serve as the escalation point to ensure your team never feels "stuck."
• Promote Inclusive Growth: Create a psychologically safe and inclusive environment where diverse perspectives are valued and team members are empowered to do their best work.
• Iterate on Process: Analyze team performance data to identify and address moments of customer pain or internal friction, refining processes for greater efficiency.
• Partner Cross-Functionally: Collaborate with upstream Advisory and downstream Fulfillment partners to ensure clean handoffs and a unified customer experience.

Required Qualifications

• 1-2+ years of people management experience in customer success, onboarding, renewals, or a similar customer-facing operations role.
• A true passion for coaching and developing individual contributors into high-performing, engaged team members.
• Exceptional verbal and written communication skills with the ability to deliver feedback that is both direct and supportive.
• Strong operational skills with a proactive approach to process improvement and a proven track record of driving process optimization efforts.
• Eagerness to leverage AI-powered tools to enhance team efficiency and customer outcomes, with a commitment to developing your team’s AI fluency.
• Experience in the health insurance and benefits space is a strong plus.

Benefits & Perks

• Compensation: $74,285/yearly - $91,000/yearly (Denver, Phoenix, Chicago, Las Vegas)
• Location: Denver, San Francisco, New York City; additional hybrid work options available based on role and candidate location.
• Schedule: Approximately 2-3 days per week in office, with flexibility for remote work on non-office days.