Jobs at Upside

Lead full-lifecycle recruiting for technical roles across Engineering, Product, and Data/Analytics. Responsibilities include role intake, sourcing, pipeline management, interview coordination, debrief facilitation, offer closing, candidate experience, ATS documentation, and recruiting process improvement. The role also develops scalable recruiting systems, templates, playbooks, scorecards, and interviewer resources while partnering closely with hiring managers and cross-functional leaders.

Own the strategy, roadmap, and growth of Upside’s restaurant vertical. Adapt incrementality measurement and offer optimization to restaurant economics, build merchant-facing reporting and onboarding products, and drive partner adoption, retention, and profitability. Partner with engineering, data science, design, sales, account management, and marketing while making integration decisions across POS, payments, and data systems. Establish OKRs and lead a 0-to-1 business area without direct authority.

Leads the Merchant & Pay engineering organization, overseeing managers and teams responsible for merchant, partner, payment, and internal tooling systems. Owns technical strategy, multi-year roadmaps, reliability, scalability, security, engineering standards, and generative AI adoption. Partners with Product, Data, Security, and company leadership while recruiting, developing, and retaining engineering talent. Requires extensive engineering leadership experience, AWS expertise, marketplace or payments experience, and experience scaling business-critical platforms.

Lead a full-stack Reconciliation team owning transaction-matching pipelines across mobile and backend systems. Drive reliability, observability, and accuracy for post-claim flows, coach and grow engineers, contribute hands-on in high-leverage technical areas, partner cross-functionally, and scale systems and processes to improve transaction success and user trust.

Own and maintain dbt data models across design, testing, deployment, monitoring, and documentation. Translate ambiguous Marketing and Product needs into reliable data solutions, write design documents, support production issues, create runbooks and schema documentation, and coach junior engineers. The role uses SQL, Python, Snowflake, dbt, Dagster, and AWS while partnering closely with Marketing, Data, and MarTech teams.

Drive application security by running SAST/SCA, threat modeling, vulnerability management, and remediation. Advise on secure architecture, train engineers, support pentests/bug bounties, and administer AWS Control Tower and IAM. Innovate with AI to improve AppSec tooling and practices.

The role involves designing and building AI-native systems for revenue teams at Upside, including developing applications, partnering with teams, managing the entire stack, and improving system reliability and performance.

Lead strategy and roadmap to build a personalized growth engine using AI and marketing technology. Define requirements across data infrastructure, multi-channel outreach, app surfaces, creative personalization, and incentive systems. Run experimentation, set KPIs, drive cross-vertical adoption, and align engineering, design, data, and marketing to scale repeatable user habits and retention.

Lead a small embedded design and research team to raise polish and consistency across consumer and payments experiences. Build design systems, embed design in discovery with Product/Engineering/Marketing, deepen research practice, apply AI-native scaling, and drive measurable outcomes for onboarding, redemption, and retention.

Lead the build-out of financial data infrastructure and automated reporting: design Snowflake-based warehouses, author SQL and dbt transformations, manage Pigment planning data, automate revenue workflows, use Python and AI for forecasting, create executive dashboards (Looker, HEX), and deliver ad-hoc strategic and M&A analytics to senior leadership and cross-functional partners.

Lead data analysis projects to help merchant partners understand Upside's impact, manage analytics relationships, and improve product strategy.

Lead data analysis for merchants, manage projects to improve product and acquisition strategies, and communicate insights effectively.

Manage enterprise restaurant accounts from onboarding through long-term growth. Improve retention, educate clients using customized data-driven materials, identify expansion opportunities, mitigate churn risk, lead monthly business reviews, interpret account data, and collaborate with analytics, product, marketing, and operations teams to strengthen retailer relationships.

Manage strategic enterprise accounts in the fuel and convenience-store industries, guiding onboarding, retention, growth, and expansion. Build account plans, conduct performance reviews, interpret data, create reports and case studies, monitor account health, address churn risks, and identify expansion opportunities. Partner with analytics, product, marketing, and operations teams while maintaining relationships with senior client stakeholders. The role includes up to 20% travel.

Drive enterprise sales growth by acquiring large fuel retail chains, wholesalers, and marketers. Build executive relationships, present a data-driven value proposition, exceed quotas, develop pipelines, manage forecasts, and onboard new merchant accounts. Partner with Sales, Product, and Marketing teams on go-to-market strategy, launches, roadmaps, and partnerships. The role requires extensive enterprise SaaS or fuel-industry sales experience, Salesforce proficiency, and 30–50% travel.

The Principal Product Marketing Manager drives customer engagement and retention strategies, creates sales enablement materials, and collaborates with teams to enhance customer value and minimize churn.