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.

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.

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

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