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
- 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, one of our company values is that we're hungry to build and learn. We believe learning new AI tools empowers us to build for our customers faster, more independently, and with higher quality. We provide these tools across all disciplines, from Engineering and Product to Sales and Support, and are inspired by how our Toasters are already driving real value with them. The people who thrive here are those who embrace changes that let us build more for our customers; it’s a core part of our culture.
Our Total Rewards Philosophy
We strive to provide competitive compensation and benefits programs that help to attract, retain, and motivate the best and brightest people in our industry. Our total rewards package goes beyond great earnings potential and provides the means to a healthy lifestyle with the flexibility to meet Toasters’ changing needs. Learn more about our benefits at https://careers.toasttab.com/toast-benefits.
Diversity, Equity, and Inclusion is Baked into our Recipe for Success
At Toast, our employees are our secret ingredient—when they thrive, we thrive. The restaurant industry is one of the most diverse, and we embrace that diversity with authenticity, inclusivity, respect, and humility. By embedding these principles into our culture and design, we create equitable opportunities for all and raise the bar in delivering exceptional experiences.
We Thrive Together
We embrace a hybrid work model that fosters in-person collaboration while valuing individual needs. Our goal is to build a strong culture of connection as we work together to empower the restaurant community. To learn more about how we work globally and regionally, check out: https://careers.toasttab.com/locations-toast.
Apply today!
Toast is committed to creating an accessible and inclusive hiring process. As part of this commitment, we strive to provide reasonable accommodations for persons with disabilities to enable them to access the hiring process. If you need an accommodation to access the job application or interview process, please contact [email protected].
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For roles in the United States, it is unlawful in Massachusetts to require or administer a lie detector test as a condition of employment or continued employment. An employer who violates this law shall be subject to criminal penalties and civil liability.
Top Skills
Toast Boston, Massachusetts, USA Office
Toast’s headquarters is located in the heart of the Seaport District. Toasters are surrounded by art, culture, and delicious cuisine in one of the most bustling neighborhoods in Boston.
Early Careers
Toast's Early Careers program is designed to launch students' careers by integrating them into the company's vibrant culture and impactful work. Interns and co-ops are treated as full-time Toasters from day one, given meaningful projects, and provided with mentorship from industry professionals. The program emphasizes hands-on learning, collaboration across teams, and the autonomy for students to develop and showcase their skills, supported by consistent feedback. Toast offers opportunities across various departments, including technical roles like Software Engineering and Data Science, as well as non-technical roles such as Human Resources and People Operations.
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