Customer Success Manager II, Payroll

Toast creates technology to help restaurants and local businesses succeed in a digital world, helping business owners operate, increase sales, engage customers, and keep employees happy. A Day in The Life As a Payroll CSM, you will serve as a strategic engine for revenue protection and customer loyalty, managing a collaborative book of business of roughly 500 locations within a regional pod structure. Your day-to-day involves a high-energy mix of leading 30-to-60-minute Zoom consultations to drive product adoption, performing deep-dive account research to identify churn risks, and acting as the definitive Payroll and Tax expert during internal QBRs and tactical problem-solving sessions. You will balance proactive outreach with reactive inbound case management, navigating complex technical de-escalations and business conversations to ensure full resolution of payroll and tax-related pain points. As we scale in 2026, you will go beyond traditional account management to help shape a scalable success model, utilizing data-driven insights and cross-functional partnerships to optimize the customer journey and ensure our expanding payroll module is a vital, high-performing component of every client’s tech stack. What you'll do (Responsibilities) Live Customer Engagement: Lead high-stakes discovery calls and product demos, delivering complex messaging with confidence and strategic redirection to meet goals. Product Technical Expertise: Master the Core POS and Employee Cloud systems to diagnose technical issues and project manage intricate customer needs toward resolution. Proactive Retention Growth: Protect and expand SaaS revenue by identifying downsell risks and executing "churn save" motions through consultative engagement. Data-Driven Optimization: Leverage product usage data and business analytics to recommend payroll process improvements and ensure clients are maximizing service value. Adoption Enablement: Drive full activation of the Payroll Product Suite by hosting educational presentations, facilitating trainings, and analyzing module usage. Cross-Functional Advocacy: Act as the "Voice of the Customer" by gathering feedback for leadership and partnering with internal teams to ensure closed-loop issue resolution. Operational Excellence: Maintain high standards for data integrity, calendar hygiene, and report building to support scalable customer success operations. What you'll need to thrive (Requirements) Payroll Tax Expertise: 2+ years of experience in B2B payroll operations, including deep knowledge of pay schedules, federal/state taxes, and benefits calculations. Account Management Pro: Proven track record in a customer-facing role focused on churn mitigation, revenue retention, and driving overall customer satisfaction. Operational Excellence: Demonstrated experience in case/queue management with a focus on data hygiene, task prioritization, and organizational efficiency. Technical Proficiency: High general tech-fluency and the ability to troubleshoot complex customer scenarios while navigating various software platforms. Communication Presence: Strong virtual presence with professional skills in negotiation, presentation, and simplified messaging for complex topics. Strategic Problem Solving: A critical and creative thinker who can move between micro-level troubleshooting and macro-level scaling in a fast-paced environment. Adaptability Autonomy: A self-starter who thrives in a constantly changing landscape and can operate independently to meet or exceed aggressive goals. What will help you stand out (Nonessential Skills/Nice to Haves) FCP or CPP credentials Bilingual in Spanish 1+ years of experience using a POS (Point of Sale) software, ideally in the service industry Work or equivalent experience in Project Management role Experience working in the tech industry or for a SAAS company Experience with Salesforce CRM, Chilipiper, MS Office, G-Suite, and Slack AI at Toast At Toast, ... (truncated, view full listing at source)