Senior Manager, Digital Upsell Strategy

Toast is driven by building the all-in-one restaurant platform that helps restaurants operate their business, increase sales, engage guests, and keep employees happy. 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. The Digital Strategist at Toast is a  high-impact growth leader responsible for optimizing the end-to-end digital customer journey across Toast's multi-product platform. This role operates at the critical intersection of all customer facing digital experiences with a direct mandate to drive value-led,  measurable business outcomes.

About this roll* (Responsibilities)

• Own performance targets for eCommerce ARR and the inbound Self-Service MQL / Upsell funnel.
• Partner closely with Product Managers across Toast Web, Toast Shop, Toast Now, and Toast IQ to embed growth levers natively into core product surfaces.
• Build and maintain a digital growth roadmap that helps customers easily discover value and select the right Toast products for their needs.
• Develop seamless end-to-end journeys across discovery, demo request, trial, and eCommerce purchase flows—working hand-in-hand with Analytics, Design, and Engineering.
• Leverage data, research, and engagement insights to develop hypotheses on how customers discover, try, use, and purchase Toast products—and translate those insights into clear experiments.
• Define and execute rigorous testing frameworks, including A/B tests and broader growth experiments to improve traffic-to-trial, trial-to-usage, and purchase conversion rates.
• Influence and align Upsell and Product leadership with compelling performance narratives and clear communication of roadmap priorities and impact.
• Translate strategy into actionable work by writing clear briefs, user stories, and requirements for Design and Engineering partners.

Do you have the right ingredients*? (Requirements)

• 10+ years working in digital customer experience, product-led growth, eCommerce, or digital product strategy
• Proven success delivering exceptionally seamless and intuitive customer journeys that drive measurable business outcomes
• Strong communicator with the ability to influence cross-functionally and translate complex work for non-technical audiences
  
  
• Demonstrated growth ownership mindset: you identify opportunities, create clarity, and execute end-to-end with autonomy
• Experience operating within cross-functional teams including Product, Design, Engineering, and Analytics

Special Sauce* (Nice to Haves)

• Experience working in a B2B or B2B2C SaaS environment for a multi-product portfolio company.
• Prior experience in roles centered around Freemium, Free Trial, or Product-Qualified Lead (PQL) conversion models.
• Proficiency with product analytics tools (e.g., Amplitude, Heap) and experimentation platforms (e.g., Optimizely, LaunchDarkly)."
• Experience in high-growth, experimentation-heavy environments

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 All jobs at Toast →Browse Remote Software Engineer Jobs →