Principal Product Manager, Personalization

Meet Upside: We created Upside to transform brick-and-mortar commerce. Our technology uses the sophistication of online retail—profit measurement, attribution, and incrementality—to provide users with more value on their everyday purchases and brick-and-mortar businesses with new, profitable customers. We’ve helped millions of users earn 2 to 3 times more cashback than any other product, and hundreds of thousands of brick-and-mortar businesses earn measurable profit. Billions of dollars in commerce run through the Upside platform every year, and that value goes directly back to our retailer partners, the consumers they serve, and important sustainability initiatives. The Impact You'll Make Upside is building a sophisticated, personalized engagement system that uses AI, marketing technology, and consumer data to bring users to the Upside app with the right message, creative, and incentive at the right moment to drive the next highest action for the consumer. This is one of Upside's highest-leverage growth opportunities, with the potential to meaningfully grow user acquisition, frequency, retention, and revenue. As the Principal Product Manager owning this space, you'll have the rare chance to build this system largely from the ground up — turning an ambitious, high-level vision into a concrete, sequenced roadmap, and making foundational calls about the systems, partnerships, and technology needed to bring it to life. What You'll Do Own the strategy and roadmap for building Upside personalized growth engine. Translating a broad, ambitious personalization vision into sequential, buildable phases. Define clear requirements and specs, and prioritize the backlog across the growth stack — data infrastructure, multi-channel outreach, app surface areas, creative personalization, and incentive systems — including build-vs-buy-vs-integrate decisions. Define success metrics and KPIs for the growth system, and use data to guide prioritization and validate impact. Lead efforts to drive multi-vertical (Fuel, Grocery, Restaurant) network adoption, identifying high-relevance users and targeting them with localized, personalized communications based on proximity to relevant retail locations. Run rapid experimentation on messaging and incentives, using results to identify what drives repeatable user habits before scaling successful patterns globally. Build a strong partnership with Upside's internal consumer marketing team, deeply understanding their needs and translating them into clear product requirements. Lead cross-functionally without direct authority, aligning engineering, design, data, and marketing around a shared roadmap and set of priorities. Competencies You'll Need 10+ years of product management experience, including leading complex, ambiguous, or platform-level initiatives. Proven track record of building scalable personalization platforms, CRM systems, or 0-to-1 products — not just isolated features. Strong quantitative and analytical skills, with hands-on experience using data and experimentation to guide product decisions. Technical fluency and ability to synthesize granular detail into clear, strategic narratives for different audiences — comfort operating at both a high strategic level and a deep analytical level is critical to this role. Exceptional communicator who builds deep cross-functional trust and can influence senior stakeholders without direct authority. Strong business acumen, with the ability to connect product decisions to retention, revenue, and broader company strategy. Deep consumer empathy and an intuitive understanding of what motivates user behavior. Location: This hybrid role is based in our Austin, Chicago, DC, or NYC office. In-office attendance is required on Monday, Tuesday, and Thursday, and may increase based on project-based needs and changes to Upside’s in-office policy over time. Compensation: The U.S. base salary range for this full-time position varies by work location: Tier 1: NYC $224,000 - $243,000 Tier 2: Austin, Chicago, Washington, DC $204,000 - $221,000 In addition to base salary, this position is also eligible for equity and benefits. The final starting pay will be determined based on job-related skills, experience, qualifications, work location, and market conditions. Your recruiter can share more about the specific salary range for your location during the hiring process. #LI-Hybrid #LI-CO1 Benefits: Medical, dental, and vision coverage starting on Day 1 Equity (ISOs) 401(k) program Family planning programs + paid parental leave Physical fitness and wellness memberships Emotional and mental health support programs Unlimited PTO + 10 paid federal holidays + our annual, week-long Winter Break Flexible work environment Lunch reimbursement for in-office employees Employee Resource Groups Learning and Development stipend Transparent culture Amazing mission! Diversity and Inclusion: Diversity drives innovation, and our differences make us stronger. We‘re passionate about building a workplace that represents a variety of backgrounds, skills, and perspectives, and we do not discriminate based on race, religion, color, national origin, gender, sexual orientation, age, marital status, veteran status, or disability status. Everyone is welcome here! If there's anything we can do to support a disability or special need during your application or interview process, please email [email protected]. This email is for accessibility accommodations only, it should not be used to submit job applications. Notice To Recruiters And Placement Agencies: This is an in-house search with a dedicated recruiter. Please do not submit resumes to any person or email address at Upside. Upside is not liable for, and will not pay, placement fees for candidates submitted by any party or agency other than its approved recruitment partners.