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.