Customer Success Manager II, SMB Account Strategy

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

The Customer Success Manager (CSM) II, SMB – Account Strategy role sits at the heart of Toast's customer retention strategy. This team engages directly with customers in real-time to understand their needs, demonstrate the value of the Toast platform, and ensure every customer has the opportunity to thrive with Toast.

In this highly visible role, you will lead consultative retention conversations, navigate contract and pricing discussions, and leverage Toast's product suite to help restaurants find every reason to continue growing with Toast. This is a high-volume, inbound and outbound engagement position that requires strict adherence to service levels, a strong phone presence, and the ability to handle complex conversations with confidence and empathy.

Account Strategy CSMs partner closely with cross-functional teams and senior leadership, operating in a focused, data-driven motion with clear success metrics tied to retention, customer outcomes, and long-term growth on Toast.

What you'll do (Responsibilities)

• Staff a dedicated high-volume Account Strategy phone and chat line with adherence to service levels and schedule, engaging customers in real-time to understand their needs and ensure they are set up for long-term success on Toast

• Lead consultative, value-based retention conversations tailored to each customer's unique business and tech stack, helping them realize the full potential of the Toast platform

• Navigate complex customer conversations with professionalism, empathy, and confidence — including objection handling, competitive discussions, and contract and pricing negotiations

• Diagnose customer needs quickly and identify the best path forward to help each customer continue to grow and succeed with Toast

• Accurately document interactions, outcomes, and customer feedback with strong attention to data hygiene, case management, and reporting

• Leverage data, account insights, and internal tools to inform retention strategies and real-time decision-making

• Act as the voice of the customer, surfacing insights and competitive trends to internal partners and leadership to continuously improve the customer experience

• Operate in a focused, repeatable motion designed to work at scale while delivering exceptional, personalized customer experiences

• Collaborate cross-functionally with Sales, Support, Product, and Finance to drive customer outcomes and support escalation paths

What you'll need to thrive (Requirements)

• 2+ years of Account Management, Customer Success, or retention-focused experience with a track record of driving positive customer outcomes

• Experience working in high-volume, queue- or case-based environments with adherence to service levels and strong prioritization in real time

• Comfort navigating high-stakes, complex customer conversations with confidence and professionalism

• Strong objection handling, negotiation, and influencing skills, especially in live customer conversations

• Proven ability to operate independently while handling competing priorities in a fast-paced, changing environment

• Data-driven mindset with the ability to interpret account insights and apply them in real-time decision-making

• Strong phone presence with excellent communication, presentation, and written skills

• Self-starter with the ability to quickly assess complex scenarios and drive toward resolution

What will help you stand out (Non-essential Skills/Nice to