Upside

Own and optimize Consumer Operations systems, develop VOC insights, and lead AI and automation initiatives. | Extensive experience in technical system ownership, data analysis, AI integration, and cross-functional collaboration in a high-growth environment. | 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. Role Overview The Senior Systems & Technology Manager is responsible for the design, optimization, and evolution of the Consumer Operations technology stack. This role serves as the technical owner for key operational systems and integrations, with a strong mandate to identify, build, and scale AI-enabled solutions that improve customer experience and materially reduce operational costs. This role operates at a highly autonomous level, partnering closely with Product and Engineering while remaining deeply embedded in Consumer Operations. Success requires strong technical depth, systems thinking, and the ability to translate operational pain points into scalable technical solutions. Primary Focus Areas Voice of the Customer (VOC) Reporting & Insights: Be a thought leader/owner in the development and maintenance of reporting that surfaces Voice of the Customer (VOC) insights across Consumer Operations channels. Build scalable, automated reports and dashboards that highlight customer sentiment, recurring issues, friction points, and experience trends. Partner with Consumer Operations, Product, and Marketing to ensure VOC insights are actionable and regularly incorporated into decision-making. Use data to connect customer feedback to operational drivers and improvement opportunities. Systems Ownership & Integration: Own the operational effectiveness of core Consumer Operations systems, including Zendesk, Retool, Slack integrations, and related tooling. Ensure systems are stable, scalable, well-integrated, and optimized for frontline and back-office teams. Act as the technical point of accountability for system enhancements, integrations, and issue resolution. Proactively identify gaps or inefficiencies in the current tech stack and propose durable solutions. AI & Automation Strategy: Research, evaluate, and build AI and automation opportunities to enhance the Consumer Operations technology stack. Partner directly with Product and Engineering to design and build AI-powered tools that: Reduce Consumer Operations OpEx Improve agent efficiency and response quality Enable smarter routing, triage, and decision support Lead proof-of-concept development, pilots, and scaled rollouts of AI-enabled solutions. Ensure AI implementations meet standards for accuracy, security, customer trust, and regulatory compliance. Required Qualifications: 8+ years of experience in a fast-paced, high-growth environment (fintech or similarly regulated industry preferred) Strong technical background with hands-on experience in: SQL / MySQL Python/Java or similar backend programming languages Demonstrated experience building operational reporting and dashboards to support Voice of the Customer (VOC) or customer experience initiatives Experience working with modern analytics and data platforms such as Snowflake, Hex, Looker, or similar tools Demonstrated experience working with AI and LLM-based systems, including: Model integration and orchestration AI-assisted workflows or automation Evaluation of model performance and quality Experience designing and supporting complex system integrations Proven ability to work cross-functionally with Product, Engineering, and Operations 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 US base salary range for this full-time position is $130,000 - $150,000 + 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-Hybrid #LI-NE1 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.

Manage and optimize consumer operations systems, develop VOC insights, and lead AI and automation initiatives. | Extensive experience in technical system ownership, data platforms, AI/LLM systems, and cross-functional collaboration in a high-growth environment. | 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. Role Overview The Senior Systems & Technology Manager is responsible for the design, optimization, and evolution of the Consumer Operations technology stack. This role serves as the technical owner for key operational systems and integrations, with a strong mandate to identify, build, and scale AI-enabled solutions that improve customer experience and materially reduce operational costs. This role operates at a highly autonomous level, partnering closely with Product and Engineering while remaining deeply embedded in Consumer Operations. Success requires strong technical depth, systems thinking, and the ability to translate operational pain points into scalable technical solutions. Primary Focus Areas Voice of the Customer (VOC) Reporting & Insights: • Be a thought leader/owner in the development and maintenance of reporting that surfaces Voice of the Customer (VOC) insights across Consumer Operations channels. • Build scalable, automated reports and dashboards that highlight customer sentiment, recurring issues, friction points, and experience trends. • Partner with Consumer Operations, Product, and Marketing to ensure VOC insights are actionable and regularly incorporated into decision-making. • Use data to connect customer feedback to operational drivers and improvement opportunities. Systems Ownership & Integration: • Own the operational effectiveness of core Consumer Operations systems, including Zendesk, Retool, Slack integrations, and related tooling. • Ensure systems are stable, scalable, well-integrated, and optimized for frontline and back-office teams. • Act as the technical point of accountability for system enhancements, integrations, and issue resolution. • Proactively identify gaps or inefficiencies in the current tech stack and propose durable solutions. AI & Automation Strategy: • Research, evaluate, and build AI and automation opportunities to enhance the Consumer Operations technology stack. • Partner directly with Product and Engineering to design and build AI-powered tools that: • Reduce Consumer Operations OpEx • Improve agent efficiency and response quality • Enable smarter routing, triage, and decision support • Lead proof-of-concept development, pilots, and scaled rollouts of AI-enabled solutions. • Ensure AI implementations meet standards for accuracy, security, customer trust, and regulatory compliance. Required Qualifications: • 8+ years of experience in a fast-paced, high-growth environment (fintech or similarly regulated industry preferred) • Strong technical background with hands-on experience in: • SQL / MySQL • Python/Java or similar backend programming languages • Demonstrated experience building operational reporting and dashboards to support Voice of the Customer (VOC) or customer experience initiatives • Experience working with modern analytics and data platforms such as Snowflake, Hex, Looker, or similar tools • Demonstrated experience working with AI and LLM-based systems, including: • Model integration and orchestration • AI-assisted workflows or automation • Evaluation of model performance and quality • Experience designing and supporting complex system integrations • Proven ability to work cross-functionally with Product, Engineering, and Operations 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 US base salary range for this full-time position is $130,000 - $150,000 + 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-Hybrid #LI-NE1 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.

Manage and oversee the full month-end close process, review account reconciliations, and lead the accounting team, ensuring compliance and accuracy in financial reporting. | 7+ years of relevant accounting experience, CPA license, strong US GAAP knowledge, experience with automation or analytics in accounting, and team leadership skills. | 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: We are expanding our product offerings to serve a wider range of customers and verticals, which necessitates growing our Accounting team with intelligent, driven, and inquisitive individuals—and that’s where you fit in! This role, reporting directly to the Controller, involves managing the full month-end close process, reviewing account reconciliations, and overseeing the expense reporting system. A key part of the role is to lead, mentor, and develop other members of the team. The role works closely with all functional areas to provide operational support and requires significant collaboration and communication skills. Lead and develop a small but high-performing accounting team, fostering a culture of innovation, accountability, continuous improvement, and automation. Oversee all aspects of the monthly and annual close process, including preparation of complex month-end journal entries Oversee the employee expense reporting system. Partner with business stakeholders to ensure business decisions are appropriately accounted for in the financial statements Direct all financial statement audits and income tax reporting with third party providers. Provide technical accounting guidance on complex transactions, new accounting standards, and emerging issues to ensure compliance and accurate financial reporting Competencies You Have: 7+ years of relevant accounting experience and an active CPA license Public accounting and corporate accounting experience is preferred Strong understanding of US GAAP accounting is required Proficiency with NetSuite or a similar software product is a plus Experience implementing automation, AI, or advanced analytics in accounting operations Experience supervising or leading a team Location: This hybrid role is based in our DC 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 $150,000 - $162,000 + 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-CO #LI-Hybrid 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.

Engineers at Upside are expected to gather context and take calculated risks to drive high-quality software and user experiences. They will partner with cross-functional teams and drive quality through documentation and clear expectations on delivery. | Candidates should have a curiosity for improving quality and a passion for building user experiences that drive business value. Foundational debugging skills and a desire to apply generative AI across the software development lifecycle are also important. | 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, engineers are expected to gather the right context from those around them and take thoughtful, calculated risks. By doing so, we help our teams move quickly and make informed decisions that lead to high quality software and delightful user experiences. We're looking for engineers who are curious about the “why” behind what we build, and strive to understand the bigger picture so they can make better technical choices. We value individuals who seek out opportunities to improve our systems and deliver real business impact through their work. We embrace change and foster open conversations to help ideas evolve and grow. Here are some ways we have seen engineers drive impact at Upside: Help cultivate a collaborative and safe environment. You can speak up to name problems, which will invite conversations that will then drive solutions. Learn and innovate on the ways we can improve our system. You are able to hone in on gaps in quality, security, performance, and speed of execution and generate buy-in to raise those bars. Partner deeply with cross functional teams. Whether it’s aligning with marketing on experimentation, enabling better personalization with data science, or integrating feedback from designers, you are proactive in surfacing insights and turning them into technical action. Drive quality through documentation. You record your decisions, communicate tradeoffs, and ensure others can build upon your work. Set clear expectations on delivery. We all understand that plans change. You focus on setting an accurate and achievable goal from the start, and then keeping close alignment with key partners when milestones shift. Why You Should Apply: Engineers come in many different shapes and sizes. I thought it would be helpful to highlight what I’m looking for on my team. This role is a good fit for you if: You aren’t afraid to challenge the status quo when it makes the team and business better. You learn from those around you while utilizing data to advocate for informed change. You thrive at the intersection of systems and storytelling. Whether exploring the root cause of a bug or building a feature set, you bring empathy and desire to improve the experience for both internal team members and end users—and build solutions that empower others to experiment, iterate, and act confidently. You care about building resilient systems that scale. You bring a mindset of continuous improvement, and know when to invest in observability or automation to reduce toil and improve outcomes for the team and end users. You believe that pulling quality upstream starts with engineering. You champion best practices, encourage early testing and validation, and work closely with peers to build a culture of quality from the ground up. Engineering Culture: We want our engineers to have the time and support to grow in their craft and contribute meaningfully to impactful technical decisions. Engineers are encouraged to focus deeply on their work, collaborate effectively with team members, and continuously develop their skills. Teams are thoughtfully staffed to create a dynamic and diverse environment that enhances learning and innovation. Technology Stack: We don’t require them all, but love those that have experience in or are interested in learning: Kotlin Multiplatform, Compose Multiplatform, Swift, and Python. Other areas of our engineering stack include Java, AWS (Cognito, API Gateway, Lambda, DynamoDB, Cloudwatch, EventBridge), Snowflake, DBT, React, Java services, and Github Actions. We also leverage numerous AI tools, including OpenAI, AWS Bedrock, and Github Copilot. Ideal qualifications: Innate curiosity for improving quality and observability Passionate about building buttery smooth user experiences that drive measurable business value Analytical mindset with a knack for experimenting, learning, iterating, and growing Foundational debugging skills to see user data, build hypotheses of what that data means, and make meaningful improvements A desire to apply generative AI across the SDLC (from ideation and design to coding, testing, and release) to boost velocity and quality 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 US base salary range for this full-time position is $120,000 - $145,000 + 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. 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.

Build scalable, resilient systems with a focus on quality, observability, and measurable business impact while collaborating cross-functionally in a hybrid environment. | Senior-level engineering experience with strong technical depth, mentoring skills, analytical mindset, proficiency in web fundamentals, automated testing, and a desire to apply generative AI. | 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, engineers are expected to gather the right context from those around them and take thoughtful, calculated risks. By doing so, we help our teams move quickly and make informed decisions that lead to high quality software and delightful user experiences. We're looking for engineers who are curious about the “why” behind what we build, and strive to understand the bigger picture so they can make better technical choices. We value individuals who seek out opportunities to improve our systems and deliver real business impact through their work. We embrace change and foster open conversations to help ideas evolve and grow. Here are some ways we have seen engineers drive impact at Upside: Help cultivate a collaborative and safe environment. You can speak up to name problems, which will invite conversations that will then drive solutions. Learn and innovate on the ways we can improve our system. You are able to hone in on gaps in quality, security, performance, and speed of execution and generate buy-in to raise those bars. Partner deeply with cross functional teams. Whether it’s aligning with marketing on experimentation, enabling better personalization with data science, or integrating feedback from designers, you are proactive in surfacing insights and turning them into technical action. Drive quality through documentation. You record your decisions, communicate tradeoffs, and ensure others can build upon your work. Set clear expectations on delivery. We all understand that plans change. You focus on setting an accurate and achievable goal from the start, and then keeping close alignment with key partners when milestones shift. Why You Should Apply: Engineers come in many different shapes and sizes. I thought it would be helpful to highlight what I’m looking for on my team. This role is a good fit for you if: You aren’t afraid to challenge the status quo when it makes the team and business better. You learn from those around you while utilizing data to advocate for informed change. You thrive at the intersection of systems and storytelling. Whether creating helpful insights for merchants tracking their value on the platform, providing accurate billing or payments or ensuring the customer journey is well understood, you bring empathy for both merchants and consumers.—and build solutions that empower others to experiment, iterate, and act confidently. You care about building resilient systems that scale. You bring a mindset of continuous improvement, and know when to invest in observability, automation, or new infrastructure to reduce toil and improve outcomes for the team and end users. You believe that pulling quality upstream starts with engineering. You champion best practices, encourage early testing and validation, and work closely with peers to build a culture of quality from the ground up. Engineering Culture: We want our engineers to have the time and support to grow in their craft and contribute meaningfully to impactful technical decisions. Engineers are encouraged to focus deeply on their work, collaborate effectively with team members, and continuously develop their skills. Teams are thoughtfully staffed to create a dynamic and diverse environment that enhances learning and innovation. Technology Stack: We don’t require them all, but love those that have experience in or are interested in learning: React, Typescript, Python, Snowflake, DBT, AWS (including API Gateway, Lambda, DynamoDB, Cloudwatch, EventBridge),Terraform and Github Actions. We also leverage numerous AI tools, including OpenAI and Github Copilot. Ideal qualifications: Lead with technical depth and continuously improve quality and observability Guide, mentor and upskill the team to raise overall effectiveness and impact Drive experiences that deliver measurable business value Apply an analytical mindset to experiment, learn, iterate and grow Debug complex systems by interpreting data, forming hypotheses and making meaningful improvements Build with semantic HTML, CSS, and core JavaScript concepts Apply strong knowledge of core web and browser fundamentals (e.g., how a browser parses and constructs a web page) Write reliable automated tests as a foundation for quality Demonstrate a proven ability or strong desire to apply generative AI across the SDLC, from ideation and design to coding, testing and release, to increase velocity and quality 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 US base salary range for this full-time position is $180,000 - $210,000 + 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. 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.