Senior Manager, Deal Desk & Business Operations

Are you bready* for a change?

We are a rapidly growing company that’s revolutionizing the way the restaurant industry does business by pairing technology with an extraordinary commitment to customer success. We help restaurants streamline operations, increase revenue, and deliver amazing guest experiences through our platform that combines restaurant point of sale, guest-facing technology, and award-winning customer support. Join us as we empower the restaurant community to delight guests, do what they love, and thrive. 

We are seeking a Senior Manager, Deal Desk & Business Operations to lead and scale operational support for Toast’s rapidly expanding Mid-Market and Enterprise segments. This is a high-impact role at the intersection of strategy, execution, and cross-functional collaboration. This role owns and drives the Deal Desk process for Mid-Market and Enterprise customers, ensuring high-quality execution and operational excellence across the sales lifecycle. You will lead a growing team that supports complex, high-value deals and partners with senior stakeholders across Sales, Services, Legal, Finance, and Product to enable frictionless growth and long-term customer success.

As a strategic leader on the Business Operations team, you will design and optimize the systems, processes, and policies that empower our Mid-Market and Enterprise sales motion. Your ability to solve ambiguous problems, communicate with clarity, and influence stakeholders will be essential to removing friction from the sales cycle and enabling scalable, sustainable growth.

About this roll * (Responsibilities):

• Own and lead the Deal Desk function for Mid-Market and Enterprise segments, ensuring consistent, scalable support for complex, high-value deals from structuring through execution.Partner closely with Sales and other stakeholders to advise on optimal deal structures based on scalability, operational feasibility, and historical precedent, ensuring alignment with business goals and cross-functional requirements.
• Own and Lead the Mid-market/Enterprise Business Operations function, managing a team who support pre- and post-sale deal execution for large restaurant groups and franchises. Ensure all work is delivered accurately and on time, in alignment with established service level agreements (SLAs).

• Serve as the primary point of escalation for operational challenges tied to high-value and complex Enterprise deals, applying critical thinking and problem-solving skills to drive resolution quickly and efficiently.
• Build and nurture strong cross-functional partnerships across Sales, Legal, Finance, Product, and Services to align on goals, streamline operations, and accelerate deal velocity.
• Define and drive operational strategy to support Enterprise growth, identifying and implementing scalable processes, tooling improvements, and policies that enhance efficiency and customer satisfaction.
• Own operational forecasting, and key performance indicators (KPIs); communicate insights clearly to senior stakeholders to influence strategic decisions.
• Champion cross-functional collaboration and change management, influencing without authority to build consensus and drive initiatives forward.
• Lead, coach, and develop a high-performing team, instilling a culture of accountability, continuous improvement, and strong communication.
  
  

Do you have the right ingredients? (Requirements):

• 10+ years of relevant experience in business operations or revenue operations, and deal desk, with at least 3 years in people management.
• Strong experience supporting Enterprise or complex B2B sales cycles, ideally in SaaS, FinTech, or other high-growth environments.
• Exceptional problem-solving and critical thinking skills with the ability to thrive in ambiguity and resolve issues that span systems, teams, and functions.
• Excellent written and verbal communication skills with a proven ability to distill complexity and drive alignment across diverse stakeholders.
• Proven track record of strong cross-functional partnership and the ability to influence at all levels of the organization, including executive leadership.
• Demonstrated success in building scalable processes, driving operational efficiency, and leveraging data for decision-making.
• Highly proficient in Salesforce and Excel; familiarity with CPQ, CLM tools (Ironclad), and BI platforms (e.g., Looker, Tableau) is a plus.
• Experience hiring, leading, and developing high-performing teams with a focus on coaching and strategic impact.

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.

*Bread puns encouraged but not required