AI Enablement Lead

About Upside

Upside was created to transform brick‑and‑mortar commerce. Our technology brings the sophistication of online retail—profit measurement, attribution, and incrementality—to everyday purchases, delivering more value to users and profitable customers to brick‑and‑mortar businesses. We’ve helped millions of users earn 2‑3 times more cashback than any other product and hundreds of thousands of businesses earn measurable profit. Billions of dollars in commerce run through the Upside platform each year, returning value to retailer partners, consumers, and sustainability initiatives.

The Opportunity

Upside is building Ascent, a shared layer of connections, encoded company knowledge, and tooling that sits on top of Claude Enterprise. Ascent enables AI value without requiring every employee to build a one‑off setup. The AI Enablement Lead will own Ascent’s roadmap end‑to‑end, spanning the engineering‑focused Software Factory and the company‑wide Enterprise Track. This role translates a fast‑moving, technical platform into sequenced priorities, clear specs, and actionable decisions for the business. The position reports directly to the VP of R&D Intelligence, Systems and Enablement (RISE).

Why This Role Exists Now

Upside’s AI enablement is shifting from point solutions to platform investment. Point‑solution adoption plateaus, while a platform requires a single owner to hold the roadmap, make sequencing calls across programs of differing maturity, and ensure the infrastructure delivers measurable business value. The AI Enablement Lead will provide that ownership, balancing trade‑offs and keeping the roadmap coherent as the underlying AI tooling evolves.

Key Initiatives

• Own the Full‑Ascent Roadmap

  Ascent comprises two programs on shared infrastructure: Software Factory (engineering) and the Enterprise Track (non‑technical users). You will prioritize and sequence work across both, making trade‑off decisions where shared infrastructure benefits both programs, where paths diverge, and how to advance the Enterprise Track without stalling Software Factory.

• Close the Enterprise Track’s Maturity Gap

  The Enterprise Track trails Software Factory on six capabilities: connected systems, Upside‑native knowledge, marketplace for reusable AI skills, “gets smarter” feedback, automated repeatable workflows, and safe AI‑assisted building. You will define the roadmap to close this gap, decide which capability to invest in first, set “good enough” criteria, and prove value for the Enterprise Track.

• Build the Feedback Loop That Ties Ascent to Business Value

  Current “gets smarter” capability lacks automated insight. You will own instrumentation, reporting, and a model that quantifies the business value of each skill or agent, ensuring the roadmap is driven by evidence rather than anecdote.

Ongoing Responsibilities

• Partner with the Ascent engineering teams as a product owner: own the roadmap, specs, and prioritization while they handle technical execution and design.
• Own and maintain the Ascent roadmap across both Software Factory and the Enterprise Track, accountable for sequencing and trade‑offs.
• Write clear specs and requirements so engineering teams can execute without your constant presence.
• Track and report on Ascent’s maturity across core capabilities, using data to justify future investments.
• Represent Ascent to stakeholders outside RISE, communicating its current state, limitations, and upcoming work in language that resonates with non‑technical audiences.
• Stay current and hands‑on with AI coding/agent tooling to ensure the roadmap reflects real friction and capability gaps.

Requirements

• 5‑8 years leading platform‑level or 0‑to‑1 initiatives from ambiguity to a working roadmap.
• Deep, hands‑on experience building with AI coding agents and AI developer tooling; able to prototype with agents to identify capability gaps.
• Demonstrated ability to write specs and drive prioritization across a technical program without direct authority over the builders.
• Strong written and verbal communication skills for translating technical concepts to engineers, executives, and broader audiences.
• A “first‑hire” mindset: comfortable establishing roadmap and operating rhythm for a role without an existing template.
• Preferred: experience in AI/developer‑tools product management, internal platforms, or AI‑enablement products.
• Preferred: experience partnering across teams with varying technical and organizational maturity.
• Preferred: familiarity with adoption/enablement motions (rollout, communications, training).
• Background in a scaling tech company where the role’s function was still being defined.

Location

This hybrid role is based in our Austin, Chicago, Washington DC, or New York City office. In‑office attendance is required on Monday, Tuesday, and Thursday and may increase based on project needs and changes to Upside’s in‑office policy.

Compensation

The U.S. base salary range for this full‑time position is $200,000 – $220,000, plus equity and benefits. Final starting pay will be determined based on skills, experience, qualifications, work location, and market conditions.

Benefits

• Medical, dental, and vision coverage starting on Day 1
• Equity (ISOs)
• 401(k) program
• Family planning programs and paid parental leave
• Physical fitness and wellness memberships
• Emotional and mental health support programs
• Unlimited PTO plus 10 paid federal holidays and an annual week‑long Winter Break
• Flexible work environment
• Lunch reimbursement for in‑office employees
• Employee Resource Groups
• Learning and Development stipend

Diversity and Inclusion

Diversity drives innovation, and our differences make us stronger. We are 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 you need accommodations during the application or interview process, please email accommodations@upside.com (accessibility accommodations only).