Senior Manager, Digital Upsell Strategy at Toast

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 https://careers.toasttab.com/toast-benefits.

The base salary range for this role is listed below. The starting salary will be determined based on skills and experience. In addition to base salary, our total rewards components include cash compensation (overtime, bonus/commissions, if eligible), benefits, and equity (if eligible).

Pay Range

$136,000—$218,000 USD

Diversity, Equity, and Inclusion is Baked into our Recipe for Success

At Toast, our employees are our secret ingredient—when they thrive, we thrive. The restaurant industry is one of the most diverse, and we embrace that diversity with authenticity, inclusivity, respect, and humility. By embedding these principles into our culture and design, we create equitable opportunities for all and raise the bar in delivering exceptional experiences.

We Thrive Together

We embrace a hybrid work model that fosters in-person collaboration while valuing individual needs. Our goal is to build a strong culture of connection as we work together to empower the restaurant community. To learn more about how we work globally and regionally, check out: https://careers.toasttab.com/locations-toast.

Apply today!

Toast is committed to creating an accessible and inclusive hiring process. As part of this commitment, we strive to provide reasonable accommodations for persons with disabilities to enable them to access the hiring process. If you need an accommodation to access the job application or interview process, please contact candidateaccommodations@toasttab.com.

------

For roles in the United States, it is unlawful in Massachusetts to require or administer a lie detector test as a condition of employment or continued employment. An employer who violates this law shall be subject to criminal penalties and civil liability.

Senior Manager, Digital Upsell Strategy

Job Description