Customer Success Manager II - Payroll
Toast is driven by building a comprehensive solution that helps operators adapt, take control, and get back to what they do best: building the businesses they love.
Bready* to make a change?
In service to protecting revenue and creating raving fans, Customer Success Managers (CSMs) within the Payroll Success Team / Customer Success Organization will engage with customers at various milestones along the customer journey. Through targeted engagements and organized meeting schedules in our queue, our Payroll Customers have the opportunity to collaborate with our strategic team to drive their business success. Our core goals include downsell prevention, technical de-escalation, long term strategic partnership & revenue retention. Customers, internal teams, and senior leadership can also request Payroll Success assistance on an as-needed basis for success-related matters. As we grow in 2026 and expand our offerings to a larger customer base, module specific focus is needed! We are adding individuals to the team that will contribute work within our Payroll vertical and help us bring this module to life
CSMs engage in email communication and one-on-one interactions in thirty-minute to one-hour Zoom or phone meetings with customers. These meetings include but are not limited to - reviewing best practices, discussing activation and adoption strategies, facilitating crucial conversations aligned with business needs, and resolving pain points or de-escalating situations. Through targeted outreach, both proactive and reactive, this role targets life cycle moments that are both technical and crucial to longevity on the platform. Additionally, CSMs are responsible for inbound case assignments through email channels and will engage with customers digitally to resolve open issues or questions.
CSMs will be responsible for a dedicated, collaborative Book of Business, with roughly 500 locations assigned to you. But working as part of a larger pod, you will be responsible for a region or customer profile type and share a larger book of business by combining all locations and supporting your peers in a Pod Support Structure. Additionally, you will support customers in partnership with CSMs across all market segments - as a strategic internal partner, you are responsible for joining QBRS, tactical problem solving and clear ownership of the Payroll Module inclusive of the tax experience end to end. In this role, you will delve into technical and strategic initiatives with the customer, manage your time effectively, optimize customers' time, and deliver an exceptional customer experience. It extends beyond the traditional customer success manager position, as you will be instrumental in shaping a scalable customer success model. We seek an adaptable, flexible, and change-motivated individual to join our team.
About this roll* (Responsibilities)
- Live customer interaction! This role is all about meeting new customers, getting on camera & navigating strategically, efficiently and confidently. You can run a demo, deliver complex messaging in a simplified & concise manner and can redirect or transition conversations to accomplish your goals.
- Confidently navigate the Core POS System & partners and expertly navigate our Employee Cloud product
- Proactive Engagement: Interpreting data, you’ll regularly engage with clients to ensure they are satisfied and are maximizing the value of the payroll and POS services
- Take ownership of customer outcomes, issues and their experience by ensuring closed feedback loops and full resolutions in partnership with cross functional teams and partners.
- Leverage a thorough understanding of the business and payroll vendor services to recommend continuous improvements to payroll processes
- Technical focus & solution minded - you are driven by solving for intricate problems and project managing customer needs towards resolution
- Self investment into knowledge growth - education minded in order to continuously support customer at scale
- Data Driven - you leverage data to make informed decisions on behalf of the customer and the business
- Ability to diagnose customer issues, develop strategies, and make leverage cross-functional partners
- Retain & grow SaaS revenue through consultative engagement and product recommendation by understanding needs of each customer, tech stack analysis & conversation. Hosting demos and discovery calls are included in this motion
- Drive activation and adoption across the Payroll Product Suite by analyzing product module usage and leverage internal tools/customer marketing strategies/cross functional teams to deliver presentations, education & facilitate trainings
- Downsell & Churn Saves Motion - interacting with customers to understand and document pain points with guest modules, discuss contract terms and enable customers to best use our modules. Protect against Product Churn as a core function of the role
- Data entry, calendar hygiene and report building is vital to success in this role and is a crucial component on your daily activities
- Act as the voice of customer by gathering feedback and insight to relay to internal partners & leadership
- Actively look for opportunities to operate at scale
Do you have the right ingredients*? (Requirements)
- 2+ years of Account Management experience, responsible for customer satisfaction, churn mitigation and business operations
- Expert knowledge of Payroll Processes & Fundamentals - inclusive but not limited to - pay schedules, federal & state laws and taxes, accounting & reporting, calculations, benefits & deductions
- Significant experience within Payroll and Tax Operations in customer facing roles
- Case / Queue Management Experience - responsible for organization, data hygiene and prioritization management
- Success operating independently and navigating competing priorities in a constantly changing environment
- General technical proficiency using a variety of software
- Proven track record of success in meeting and exceeding goals
- Self starter & ability to work autonomously - ability to dive into complex customer scenarios and forge a path forward
- Strong & Professional Virtual Presence - Excellent communication, organizational, and influencing skills (including written communication, negotiation and presentation skills)
- Flexibility & adaptability - we move quickly and introduce change consistently - an open mind is key to success!
- Problem solving mindset - critical & creative thinker and someone who thinks at scale - you towards the macro & are excited to work in a dynamic, fast paced environment.
Special Sauce* (Non-essential 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
Our Spread* of Total Rewards
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.
#LI-DNI
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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