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

In service to protecting revenue and creating raving fans, Customer Success Managers within the Payroll Success Partners team drive business growth through targeted lifecycle engagements. As we expand our Payroll vertical in 2026, this role focuses on core goals including downsell prevention, technical de-escalation, revenue growth, and long-term retention. CSMs engage both proactively and reactively through daily inbound cases, targeted call-downs, texting sessions, and 30- to 60-minute Zoom or phone meetings. By guiding adoption strategies, reviewing best practices, managing renewals, project managing technical inbound questions and de-escalating high-risk accounts, CSMs are expected to "go beyond the ask"—transforming reactive inquiries into strategic, value-driven partnerships that prevent churn.

Operating within a collaborative Pod Support Structure, each CSM is capable of managing ~500 locations, rotationally supporting over 3,000 shared regional locations across a team of 6. This shared model relies on clear communication, ownership and timeliness. This highly adaptable role demands strong cross-functional partnership to tackle tactical problem-solving and ensure clear, end-to-end ownership of the Payroll Module and tax experience. Beyond traditional duties, change-motivated CSMs will balance technical deep-dives with overarching strategic initiatives, playing an instrumental role in shaping a scalable, exceptional customer success model for our expanding user base.

What you'll do (Responsibilities)

• Build trust through high-touch, live video interactions across all lifecycle stages.
• Drive renewal conversations, expand SaaS revenue, and execute churn/downsell save motions through consultative strategies.
• Synthesize client feedback, pain points, and product usage to advocate for customer needs with leadership and internal teams.
• Act as a subject matter expert across the Payroll Product Suite, Employee Cloud, Core POS, and partner integrations.
• Project-manage intricate technical issues to full resolution alongside cross-functional partners.
• Analyze tech stacks and workflows to recommend continuous payroll process improvements for clients and internal teams.
• Monitor product usage data to deliver targeted presentations, education, and trainings that drive adoption.
• Simplify complex technical messaging to ensure customers realize the full value of the service offering.
• Leverage AI and internal tools to optimize daily workflows and scale customer support efforts.
• Maintain strict administrative rigor through CRM data entry, calendar management, and accurate reporting.
• Continuously expand domain and product knowledge to stay ahead of industry standards.

What you'll need to thrive (Requirements)

• 2+ years of Account Management experience, responsible for customer satisfaction, churn mitigation and business operations
• Expert knowledge of B2B 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 a customer facing role
• 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.

What will help you stand out (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

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.