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

Upside is seeking a Retailer & Channel Partnerships Senior Director to lead the strategy, growth, and execution of our partner ecosystem—from merchant SaaS startups to the largest financial institutions and payment platforms.

As a senior leader on the Business Development team, you will define and scale Upside’s merchant and channel partner strategy, cultivate executive-level relationships, structure and negotiate complex commercial agreements, and ensure partnerships deliver measurable growth. You will serve as the connective tissue across Sales, Product, Operations, and Marketing to bring high-impact partnerships from inception to full-scale execution.

What You’ll Do

Lead & Scale Channel Partnerships

• Build and operationalize a scalable, one-to-many enablement strategy to accelerate merchant adoption of Upside’s Pay and marketplace products.

• Drive meaningful merchant growth through channel and referral partnerships across POS platforms, processors, hardware providers, SaaS companies, and fintech partners.

• Explore and execute marketplace and embedded distribution opportunities within SaaS ecosystems while maintaining strong unit economics.

• Act as the voice of the merchant in all partner relationships.

Own Strategy & Execution

• Develop and execute a long-term partnership strategy aligned with Upside’s growth goals and vertical expansion.

• Lead cross-functional deal teams to build operational plans for each partnership and manage execution end-to-end.

• Establish performance metrics, monitor results, and ensure on-time, in-full delivery of contractual commitments.

• Champion prioritization of initiatives that maximize holistic impact while balancing product and engineering investment.

Structure & Negotiate Complex Deals

• Structure and negotiate multi-year commercial agreements across fintech, merchant processing, and retail technology ecosystems.

• Partner with Legal, Finance, Product, and Operations to deliver scalable, durable agreements that unlock long-term value.

Represent Upside Externally

• Serve as a senior external ambassador for Upside at industry forums, partner events, and merchant coalitions.

• Position Upside as the leading incremental-profit platform for brick-and-mortar businesses.

What You Bring

• 10+ years of experience in business development, strategic partnerships, corporate strategy, management consulting, or related commercial leadership roles.

• Deep experience negotiating complex commercial agreements and interpreting legal frameworks.

• Strong background in financial services, payments, retail technology, or merchant processing ecosystems.

• Experience working with ISVs, POS providers, processors, or SaaS platforms strongly preferred.

• Proven program management capability—driving technical and business implementations across cross-functional teams.

• Strong analytical and quantitative skills with a data-driven approach to decision-making.

• Ability to operate effectively in a fast-paced, matrixed, high-growth environment.

• Willingness to travel (approximately 10–40%).

• MBA or advanced degree preferred.

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 $188,000 - $224,000 + bonus + 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-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 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.