Staff Forward Deployed Engineer, GTM Platform

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

This is the first engineering hire on a new internal platform effort inside Upside's Revenue Operations organization. You'll be building a zero-to-one, AI-native system for our go-to-market teams; a substrate for agentic orchestration that is meant to take over the work our teams do today across cumbersome legacy tooling.

Reporting to the Sr. Director of Revenue Operations, you'll operate as a forward deployed engineer: embedded directly with the business, close to the people whose problems you're solving, and measured on outcomes rather than output. You'll sit with revenue teams, understand how they actually work, and build the systems that change it. You will define the architecture and technical direction of this platform.

We're deliberate about the title. The forward deployed model means deep business alignment, tight feedback loops, and a bias toward shipping something real. The difference here is that your users are internal: the teams that acquire merchants, serve partners, and drive Upside's revenue.

What you'll do

• Build the first version of an AI-native platform for Upside's go-to-market teams, working across agentic orchestration, automation, and the interfaces our revenue teams use every day

• Embed with revenue teams to learn their workflows firsthand, then design and ship systems that meaningfully change how that work gets done

• Own technical direction. You'll make the architecture calls, choose the tools, and set the patterns this platform grows on

• Move from prototype to production quickly, then keep iterating as AI capabilities change underneath you

• Anchor your work to business outcomes. Success here is measured in what the platform unlocks for the business, not in tickets closed

• Work with our security and infrastructure partners to make sure what you build is sound and supportable

• Document decisions and tradeoffs clearly so the team that follows you can build on your work

What we're looking for

• Staff-level engineering experience — roughly 8 years or comparable depth built through another path with a history of owning systems end to end

• Experience taking something from zero to one: greenfield systems, early-stage products, or internal platforms you built from nothing

• Real experience building with LLMs and AI APIs in production, including prompt design, output evaluation, and iterating toward reliability

• Fluency with AI-assisted development tools as part of how you work, not as an experiment

• Strong judgment about technical tradeoffs, and the ability to refactor and change direction as requirements shift

• Genuine interest in the business side. You'll be spending time with revenue and operations teams, and curiosity about how they work is a real requirement of this role

• The ability to work with a high degree of independence and ambiguity, and to bring stakeholders along as you go

• Clear communication with both engineers and non-engineers

We're language agnostic. We care much more about how you solve problems, make decisions, and adapt than about which languages are on your résumé. Our current prototypes lean on React, TypeScript, and Python, but you'll have real input into what this platform is built with.

Nice to have

• Understanding of CRM and revenue data models — Salesforce, HubSpot, or similar. Note that this role is about building what comes after those tools, not integrating deeply with them

• Experience as an early or founding engineer at a startup, or as the person who built an internal tooling function

• Familiarity with retrieval-augmented generation (RAG), vector databases, and embedding-based search

• Experience in marketplace or high-growth environments

• Experience with modern data platforms such as Snowflake

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 View email address on us.fitly.work.

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.