Senior Associate, Digital Upsell

Toast creates technology to help restaurants and local businesses succeed in a digital world, helping business owners operate, increase sales, engage customers, and keep employees happy.

The Sr. Associate, Digital Upsell is a high-energy, execution-focused role within Toast’s Digital Upsell team. You will own upsell funnel conversion rate optimization across Toast’s three core digital product surfaces-Toast Web, Toast Now, and Toast Shop- working at the intersection of CMS-driven content experiences and rigorous A/B testing to increase product discovery, inbound lead generation, and self-service purchase. This role reports into the Digital Upsell Lead and partners closely with Product, Design, Engineering, and Analytics to ship experiments that move the needle on upsell performance.

A Day In the Life* (Responsibilities): 

• Execute and optimize the end-to-end upsell funnel across Toast Web, Toast Now, and Toast Shop—from discovery and product detail pages through inbound lead generation and self-service purchase completion.
• Build, launch, and analyze A/B tests and growth experiments that improve traffic-to-trial, traffic-to-MQL, and purchase conversion rates across all digital surfaces.
• Partner with CMS (Contentful) and front-end engineering teams to create, iterate, and maintain high-performing product detail pages, splash pages, and upsell entry points- without requiring engineering tickets for every content change.
• Leverage product analytics tools (e.g., Amplitude) to develop hypotheses, monitor funnel health, identify drop-off points, and translate data into clear experiment briefs.
• Write clear user stories, requirements, and test plans for Design and Engineering partners, translating growth strategy into actionable sprint-ready work.
• Support the Digital Upsell Growth Lead in maintaining the digital growth roadmap and communicating experiment results, funnel insights, and performance narratives to Upsell and Product leadership.
• Collaborate cross-functionally with Product Managers, Designers, Engineers, Analytics, and Marketing to ensure seamless customer journeys across multi-product discovery flows.
• Stay current on CRO best practices, CMS capabilities, and experimentation frameworks, bringing fresh ideas and external benchmarks to the team.
• Embrace AI tools (e.g., ChatGPT, Claude, Cursor) to accelerate day-to-day workflows—from drafting experiment briefs and analyzing funnel data to generating content variations and prototyping CMS components—building faster and with higher quality.

What you'll need to thrive* (Requirements):

• 3+ years of experience in digital marketing, conversion rate optimization, product-led growth, eCommerce, or digital product strategy.
• Hands-on experience managing content on CMS-enabled surfaces (e.g., Contentful, WordPress, or similar headless CMS platforms).
• Demonstrated experience designing, executing, and analyzing A/B tests or multivariate experiments with measurable business impact.
• Strong analytical skills with proficiency in product analytics tools (e.g., Amplitude, Hex, Google Analytics) and comfort building dashboards or reports to track funnel performance.
• Excellent communication skills- you can translate complex data into clear insights and write sharp briefs that Design and Engineering teams can act on.
• Growth ownership mindset: you identify opportunities, move fast, and execute end-to-end with minimal hand-holding.
• Experience working within cross-functional teams including Product, Design, Engineering, and Analytics.
• Comfortable using AI and LLM-based tools to augment your work—whether for content creation, data analysis, or rapid prototyping—and eager to continuously learn and integrate new AI capabilities into your toolkit.

Nice to Have's: 

• Experience working in a B2B or B2B2C SaaS environment, ideally within a multi-product portfolio company.
• Familiarity with experimentation platforms (e.g., Optimizely, LaunchDarkly, or similar feature flagging tools).
• Prior experience with headless CMS architectures and component-based content delivery.
• Exposure to freemium, free trial, or Product-Qualified Lead (PQL) conversion models.
• Proficiency with tools such as Figma, Jira, or Asana for cross-functional collaboration.
• Experience in the hospitality, restaurant, or vertical SaaS space.

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.