**Description of Work:** Provide network engineering and training support for CPE C3N Trail Boss Team, Communication Systems Integration (CSI). Candidates for this position must be able to demonstrate: - Knowledge and understanding of integration, configuration, and troubleshooting of communication systems that are currently being fielded to Army Divisions and SFAB Units (Tactical Networks, Tactical Radio systems, MMC-S, Mission Command systems, etc.). - In-depth experience in training, fielding, and support for the systems mentioned above. - Knowledge and understanding current/future Force tactical and strategic military communications networks, as well as the architecture, protocols, security, network management and physics underlying these systems. - The ability to build and develop relevant training modules - The ability to conduct technical coordination between PEO, PMs and units. - The ability to conduct and coordinate sustainment/refresher training.

• Engineer, build, configure and maintain Windows, Cloud, Virtualization and Storage systems. • Administer and maintain Active Directory (AD) and Group Policy Objects (GPOs). • Manage user accounts, permissions, and security groups. • Implement Active Directory best practices and troubleshoot AD-related issues. • Administer Office 365 environment, including Exchange Online, Teams, and OneDrive for Business. • Manage and optimize virtualization platforms (e.g., VXRail/VMware/Horizon). • Oversee physical and virtual servers, monitor performance, conduct regular updates, and perform backups. • Maintain accurate and up-to-date documentation for all IT systems and procedures. • Work closely with other IT staff, departments, and external vendors to resolve technical issues.

• partner closely with business stakeholders and technology teams for enhancing web applications • play a critical part in shaping solutions and translating business needs into clear requirements • ensure quality delivery and support systems throughout their lifecycle • operate independently or as a project/team lead • provide direction across multiple concurrent initiatives balancing business value, technical feasibility, and delivery risk

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 building a new generation of internal platforms that help our go-to-market teams operate more efficiently and make better decisions. In this role, you will design and build AI-native systems that improve how revenue teams manage pipeline, analyze performance, and automate operational workflows. Reporting to the Sr. Director of Revenue Operations, you will work at the intersection of engineering, AI, and business operations, building systems that support how Upside acquires merchants, serves partners, and scales its go-to-market motion. You will help define the architecture and technical direction of these platforms as they evolve. This role is a strong fit for engineers who are curious about how GTM teams operate and enjoy translating business workflows into reliable, well-designed software systems. The ideal candidate has fully embraced and applied modern AI tools and automation to real operational challenges and enjoys owning systems end-to-end. What you’ll do: - Build high-impact applications and tools that accelerate Upside's go-to-market motion. Develop AI-native tools that help revenue teams manage pipeline, analyze performance, and automate operational workflows - Partner deeply with cross-functional teams to understand business workflows and translate them into scalable technical solutions. Prototype, iterate, ship and maintain - Own systems end-to-end. Design across the stack from front-end interfaces to backend services, automation pipelines, and AI orchestration layers - Continuously improve the systems you build. Identify opportunities to increase reliability, performance, and scalability while reducing manual work for the teams that rely on these tools - Strong understanding of prompt design and prompt engineering as a core part of building AI-powered systems, including structuring prompts, evaluating outputs, and iterating on prompt strategies to improve reliability and quality - Drive quality through clear communication and documentation. Record design decisions, communicate tradeoffs, and ensure others can build upon your work - Deliver reliably and transparently. Set clear expectations, communicate progress, and keep stakeholders aligned as priorities evolve What we’re looking for: - 8+ years of professional software engineering experience, with demonstrated depth in full-stack development (React/TypeScript plus backend/database experience) - Deep experience using AI-assisted development tools to improve engineering velocity and quality - Experience building applications or systems that leverage LLMs, AI APIs, or modern AI frameworks - Experience designing and owning internal platforms or operational systems end-to-end - Familiarity with modern deployment and infrastructure platforms (such as Supabase, Vercel, or similar environments) - Strong product intuition and the ability to translate business workflows into well-architected technical solutions - Track record of leading projects, mentoring teammates, and delivering measurable outcomes - Strong communication skills and the ability to collaborate effectively with both technical and non-technical stakeholders Nice to have - Experience working with CRM systems or revenue platforms (Salesforce, HubSpot, or similar) - Experience in marketplace or high growth-stage SaaS environments - Familiarity with retrieval-augmented generation (RAG), vector databases, and embedding-based search - Experience working with modern data platforms such as Snowflake Technology Stack: We don’t require experience with all of these technologies, but we’re excited to work with engineers who have experience in or are interested in learning: React, TypeScript, Next.js, Python (FastAPI), PostgreSQL, Supabase, Vercel, and modern API-driven architectures. We also leverage numerous AI tools across our development workflow, including OpenAI and GitHub Copilot. 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 $214,000 - $245,000 + 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-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.