GTM Systems Administrator

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.

As GTM Systems Administrator, you will play a critical role in ensuring the stability, scalability, and evolution of Upside’s go‑to‑market technology stack. You will serve as a trusted systems partner, supporting day‑to‑day systems health while also contributing to strategic initiatives that improve automation, data quality, and user experience. This role requires strong independent ownership, sound judgement in complex systems decisions, and the ability to translate business needs into durable, scalable solutions.

Reporting to the Senior Director, Revenue Operations, you will help ensure our technology ecosystem remains a reliable system of record and a catalyst for operational efficiency, including supporting emerging AI‑powered workflows and automation plays.

• Support the administration, configuration, and ongoing optimization of Upside’s GTM Technology Stack (Salesforce, Conga, Docu Sign, Outreach, Etc.), ensuring platform reliability, performance, and data integrity.

• Deliver production support by troubleshooting, prioritizing, and resolving issues raised by end users and integrated systems, with a focus on root‑cause resolution.

• Support program management for the Salesforce domain, including roadmap definition, backlog grooming, prioritization, and delivery planning in partnership with business partners.

• Partner with stakeholders to gather business requirements and translate them into scalable Salesforce solutions.

• Document business requirements, solution designs, and system behaviour to ensure clarity, alignment, and long‑term maintainability.

• Design and implement automation (including flows, validations, and AI‑enabled capabilities) to improve efficiency, reduce manual work, and support scale.

• Support AI automation initiatives by helping operationalize new Salesforce features and adjacent tools that enhance productivity and decision‑making.

• Proactively monitor Salesforce releases and broader ecosystem trends, ensuring Upside stays ahead of new functionality and practices

• Partner with Enablement and Operations leaders to support training programmes, develop user documentation, and reinforce consistent system usage.

• Act as a thought partner on systems strategy, finding opportunities to improve data quality, governance, and cross‑platform alignment.

• Collaborate with external vendors and internal technical partners to support integrations, enhancements, and platform investments.

• 4+ years of hands‑on Salesforce administration experience in a complex, fast‑paced environment (certifications preferred).

• Deep understanding of Salesforce core functionality (Sales Cloud preferred), automation tools, and data model design.

• Proven experience gathering business requirements and translating them into well‑architected system solutions.

• Strong production support mindset, with the ability to balance urgent issues against longer‑term platform improvements.

• Demonstrated ability to operate independently, prioritise competing demands, and exercise good judgement

• Strong communication and collaboration skills, with the ability to influence without authority and partner across functions.

• Salesforce

• Hubspot

• Outreach

• Gong

• Conga / Docu Sign

• n8n

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.