About this role.
Upside is hiring a Principal Product Marketing Manager to commercialize products and feature releases for its retailer-facing marketplace platform. The role connects Product and Retailer Go-to-Market teams, representing retailer needs in product strategy, roadmap discussions, positioning, pricing, and launch planning. Key outcomes include increasing adoption, enabling sales and account teams with effective product narratives, and identifying retailer use cases that can inform new offerings. This is a senior, highly cross-functional B2B SaaS product marketing role requiring strong strategic judgment, analytical rigor, and influence without direct authority.
Role DNA
A quick view of the complexity, pace, ownership and collaboration implied by the job description.
Job Complexity
5/5Pace & Pressure
5/5Autonomy Level
5/5Communication Load
5/5Salary analysis
Estimated compensation compared with the broader US market for similar roles.
Core skills
Skills and capabilities most closely associated with this opportunity.
Sample interview questions
I would begin with retailer segmentation, problem validation, and a clear assessment of the feature's differentiated value. I would then define positioning, packaging or pricing considerations, launch tiers, enablement materials, adoption metrics, and a feedback loop with sales, account teams, and early customers.
I would establish a shared decision framework grounded in customer evidence, revenue opportunity, strategic fit, implementation effort, and adoption risk. By documenting tradeoffs and communicating a clear business case, I can create alignment while ensuring retailer feedback is represented in prioritization decisions.
Effective messaging starts with the buyer's business problem and quantifies the outcome wherever possible. It should clearly explain who the product is for, how it works, why it is distinct, and the measurable value it delivers, while remaining simple enough for sales teams to use consistently.
I would track leading and lagging indicators, including target-account engagement, sales readiness, pipeline influence, activation, feature adoption, time to value, retention, expansion, customer feedback, and win-loss insights. These measures reveal whether the launch created durable customer value rather than only short-term demand.
I would interview top-performing sellers, product experts, and customers to identify the objections, proof points, and use cases that matter most. I would translate those insights into concise pitch decks, discovery guidance, battlecards, demos, and role-specific playbooks, then use feedback and conversion data to refine the materials.
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
As Upside’s Product Marketer focused on Product Commercialization, you will work at the intersection of our Product and Retailer Go-to-market (RGTM) teams to shape how retailers think about our product. Internally, your work will drive cohesion and clarity across teams. Externally, your work will drive both product adoption and top-line revenue growth by acting as the voice of the retailer during product development, and by leading the commercialization of products and feature releases.
Specifically, you will:
Champion the voice of the retailer, using market and competitive research to highlight opportunities in the product strategy.
Ensure internal alignment by acting as the primary liaison between the Product and Retailer Go to Market (RGTM) teams, to champion the voice of the retailer and align on roadmap priorities
Define our internal product GTM hierarchy in order to ensure effective and impactful launches and positive retailer reception
Contribute to our pricing strategy so that our price point reflects the product’s value, covers costs, and meets retailers’ expectations
Drive adoption of new products and features among target prospects, channel partners, and the existing Upside retailer partners
Help to discover and document new product use-cases based on retailer pain points that could turn into new solutions and product offerings
Partner with Revenue Enablement to ensure the Sales and Accounts teams are equipped to tell the product story and accelerate conversion and expansion opportunities
What you should have
7+ years of experience in product marketing, sales enablement, or a related role—preferably in B2B, SaaS, or a high-growth tech environment. Experience with marketplaces is a plus.
A proven understanding of product commercialization and experience developing strategies to drive product adoption
Outstanding messaging and positioning skills, with the ability to distill complex ideas into clear, compelling value propositions.
Proven track record of crafting high-impact sales enablement content—including pitch decks, playbooks, and competitive battle cards.
Experience working cross-functionally with sales, marketing, and product teams to align on go-to-market strategies.
Demonstrates leadership through influence, earning trust through clear communication, concrete business cases, and compelling storytelling that achieve positive outcomes.
Data-driven approach, with experience using insights to optimize sales performance and messaging.
A bias for action and results, with the ability to work independently and drive initiatives forward in a fast-paced environment.
A genuine passion for problem-solving and applying an analytical approach to each new challenge.
Resiliency, by adopting the evolving nature of the position with a willingness to take on new responsibilities as the role continues to develop and expand.
Location:
This role offers location flexibility, however, if you’re based in the Washington, D.C., Austin, Chicago, or NYC metropolitan regions, in-office attendance is required on a hybrid basis.
Compensation:
The U.S. base salary range for this full-time position is $179,000 – $215,000 + equity + 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 during the hiring process.
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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 accommodations@upside.com.
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.
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