Principal Product Marketing Manager (B2B SaaS)

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

5/5### Pace & Pressure

5/5### Autonomy Level

5/5### Communication Load

5/5AI insightThis principal-level role owns complex commercialization work across product, sales, account management, revenue enablement, and marketing in a fast-moving marketplace environment. Success requires translating retailer insights and product capabilities into measurable adoption and revenue outcomes while building alignment among senior stakeholders.

Salary analysis

Estimated compensation compared with the broader US market for similar roles.

$197,000

$160k–$230k

AI insightThe disclosed U.S. annual base-salary range is $179,000 to $215,000 USD, with a midpoint of $197,000. This is competitive for a principal-level B2B SaaS product marketing professional in the U.S.; a representative U.S. market base-salary range is approximately $160,000 to $230,000, excluding equity and benefits.

Core skills

Skills and capabilities most closely associated with this opportunity.

Sample interview questions

How would you develop a commercialization strategy for a new retailer-facing product feature?

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.

Describe how you would align Product and Retailer Go-to-Market teams when they have different roadmap priorities.

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.

What makes product messaging effective for a B2B marketplace audience?

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.

How would you measure the success of a product launch beyond initial revenue?

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.

Tell us about your approach to creating sales enablement materials for a complex product.

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 alignmentby 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 hierarchyin order to ensure effective and impactful launches and positive retailer reception- Contribute to our pricing strategyso that our price point reflects the product’s value, covers costs, and meets retailers’ expectations
• Drive adoption of new products and featuresamong target prospects, channel partners, and the existing Upside retailer partners- Help to discover and document new product use-casesbased on retailer pain points that could turn into new solutions and product offerings
• Partner with Revenue Enablementto ensure the Sales and Accounts teams are equippedto 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 commercializationand 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-functionallywith 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-solvingand 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.

#LI-REMOTE

#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 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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