Senior Program Manager

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.

About the Role

At Upside, Program Managers serve as strategic partners, systems-minded thinkers, and cross-functional leaders, driving operational excellence across R&D. We bridge strategy and execution by identifying core business challenges, developing scalable solutions, and ensuring alignment across product, engineering, design, data, and other business functions.

We’re looking for someone who thrives in ambiguity, excels at building relationships, and has the strategic depth to design solutions that drive measurable business outcomes.

Here are some ways you’d succeed at Upside:

• Drive strategic alignment and execution: Partner with R&D and business leaders to identify key challenges, design scalable solutions, and ensure initiatives deliver measurable business value.

• Lead cross-functional program delivery: Develop and manage program plans, coordinate dependencies, and facilitate forums that drive progress, accountability, and visibility across teams.

• Measure impact and ensure transparency: Define success metrics, create dashboards, and implement models that promote clarity, predictability, and data-informed decision-making.

• Champion continuous improvement: Use qualitative insights to identify bottlenecks, optimize delivery systems, and streamline how teams execute.

• Enable change and operational excellence: Empower teams to adopt new processes and behaviors, driving sustainable change and embedding a culture of accountability and efficiency.

What you Bring

• 5+ years of strategic delivery, transformation, or change management roles and/or 5+ years of program or project management experience with proven results driving large-scale, cross-functional initiatives.

• Demonstrated ability to translate strategy into actionable plans and measurable outcomes.

• Strong analytical skills with experience using data and metrics to drive continuous improvement.

• Exceptional communication, storytelling and influencing skills.

• Experience building dashboards, frameworks, or operating systems that improve visibility and decision-making.

• Familiarity with Jira, Confluence, and other project management tools.

• Basic level of experience with programming (e.g. SQL) or willingness to learn.

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 is $130,000 - $170,000 + 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.