Staff Full Stack Engineer, GTM Systems

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.

Responsibilities

• 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.

Requirements

• 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.
• 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.

Qualifications

• 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.

Skills

• React, TypeScript, Next.js
• Python (FastAPI)
• PostgreSQL
• Supabase
• Vercel
• Modern API-driven architectures
• Experience with OpenAI and GitHub Copilot

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
• Awesome mission!

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.