Senior Program Manager, Retail Strategy and Operations

About Toast

Toast is driven by building a platform that helps our customers adapt, take control, and get back to what they do best: building the businesses they love.

About the role   

Toast Retail is Toast's fastest growing new vertical. As the Senior Manager of Retail Operations & Strategy, you will be the operational backbone supporting the teams powering that growth. Reporting to the Director of Retail Operations & Strategy, this person will partner with leaders across Product, Customer Success, Care, and others to build the programs and processes that enable the Retail business to scale.

A day in the life (Responsibilities) 

• Lead and project-manage cross-functional initiatives across Care, Customer Success, and Product - driving alignment, accountability, and momentum across teams.
• Build operational programs from the ground up: identify where the business needs structure, design the process, and see it through to execution.
• Support Care Operations by improving escalation workflows, streamlining cross-functional coordination, and helping the team scale sustainably as retail customer volume grows
• Partner with the Customer Success team on account health monitoring, capacity,  and operational frameworks that help the team prioritize and perform.
• Support Product and Engineering teams with operational needs including backlog hygiene, SLA monitoring, and cross-team dependency management.
• Contribute to retail strategic planning efforts including market expansion playbooks, and mid-market growth frameworks.

What you'll need to thrive (Requirements) 

• 10+ years of professional experience, including 5+ years managing programmatic initiatives or complex project lifecycles, ideally within a post-sale environment at a technology/SaaS company.
• Bachelor’s degree
• Strong project management skills; you can drive complex, multi-stakeholder initiatives to completion without formal authority
• Analytical and comfortable with operational metrics and lightweight analyses that drive decisions
• Track record of earning trust with senior leaders and cross-functional partners across both technical and commercial teams
• Excellent written and verbal communication; you translate complexity into clear narratives for varied audiences
• Results-oriented with a bias toward action; outstanding discernment about where to focus energy to add the most value

What will help you stand out (Nonessential Skills/Nice to Haves)

• Familiarity with tools like SQL, Jira, Jira Product Discovery, Salesforce, and Notion
• Experience scaling programs in a startup environment
• Curiosity and enthusiasm for AI tools; you actively explore how AI can be applied to automate analysis, surface insights, and build lightweight operational tools that help teams move faster
• Customer Success Management experience

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.