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AI Enablement Lead

UpsideAustinEngineering
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Salary
$200K – $220K
Job type
Full-time
Work mode
Remote
Posted
20 Sept 2026
Status
Open · checked 9d ago

About this role

Role Overview

The AI Enablement Lead at Upside is a full-time hybrid position based in Austin, requiring a professional with 5 to 8 years of experience to direct the roadmap of the Ascent platform. This role suits an experienced practitioner who can translate a fast-evolving technical platform into clear priorities, actionable specs, and strategic business decisions.

Key Responsibilities

Own and manage the full-scale Ascent roadmap, balancing priorities across the Software Factory program and the Enterprise Track.
Close the maturity gap for the Enterprise Track by driving capability investments in connected systems, native know-how, and skill marketplaces.
Design and implement a feedback loop that connects AI utilization metrics directly to tangible business value.
Author clear product specifications and technical requirements so engineering teams can execute independently without direct authority.
Track, evaluate, and report on the overall maturity of Ascent across core capabilities to justify subsequent investments.
Communicate platform updates, current limitations, and upcoming features effectively to both technical and executive stakeholders.
Maintain hands-on familiarity with the modern AI agent and coding tool landscape to accurately assess capability gaps.

Requirements

Possess 5 to 8 years of professional experience leading platform initiatives or 0-to-1 projects from ambiguity to a functioning roadmap.
Demonstrate deep, hands-on experience building solutions with AI coding agents and developer tooling.
Capable of creating working code-based prototypes independently using AI agents to distinguish genuine technical gaps from general friction.
Proven ability to write detailed specifications and prioritize tasks across a technical program without holding direct management authority.
Exceptional written and verbal communication skills tailored for audiences ranging from software engineers to company executives.
Exhibit a first-hire mentality with comfort establishing operating rhythms and roadmaps for a newly defined function.

Nice to Have

Prior product management experience focusing on AI or developer-internal tools, developer experiences, or enablement products.
Experience working collaboratively across organizational units with varying levels of technical and operational maturity.
Familiarity with adoption, rollout, communication, and training motions for internal tools.
Background working within scaling technology companies where job functions were still actively defined.

Skills and Tools

AI coding agents and developer tooling
Technical product roadmap management
Specification writing and feature prioritization
Internal platform instrumentation and data reporting
Cross-functional stakeholder communication

Salary and Benefits

Base salary range of $200,000 to $220,000 per year in the U.S.
Incentive equity in the form of Incentive Stock Options (ISOs)
Medical, dental, and vision insurance coverage starting on the first day
401(k) retirement savings program
Comprehensive family planning resources and paid parental leave
Wellness, physical fitness, emotional health, and mental support memberships
Unlimited paid time off, 10 paid federal holidays, and a week-long company Winter Break
Lunch reimbursement provided for days worked from the office
Dedicated learning and development stipend

About the Company

Upside operates a commerce platform transforming brick-and-mortar retail by applying online retail analytics like profit measurement, attribution, and incrementality. Millions of consumers utilize the platform to earn increased cashback, while hundreds of thousands of retail partners gain measurable profits. Billions of dollars in commerce flow through the ecosystem, supporting local retailers, consumer savings, and environmental sustainability initiatives.

How to Apply

Interested candidates should submit their application directly through the official Upside careers page. Please note that resume submissions via third-party agencies or unauthorized email addresses are not accepted.

Questions candidates ask

What is the primary focus of the AI Enablement Lead?

The AI Enablement Lead owns the end-to-end roadmap for Ascent, which is Upside's shared AI infrastructure platform containing both the Software Factory engineering program and the Enterprise Track.

Does this role include direct reports?

No, this position has no direct reports. Influence and leadership are driven through the quality of product specifications, technical credibility, and alignment across engineering teams.

What is the salary range for this position?

The U.S. base salary range for this full-time role is $200,000 to $220,000 per year, accompanied by equity and comprehensive benefits.

Where is this job located?

This hybrid role is based out of the Austin office, alongside options for Chicago, DC, or NYC, with mandatory in-office attendance on Mondays, Tuesdays, and Thursdays.

What level of experience is required?

Candidates must have 5 to 8 years of experience leading platform-level or zero-to-one initiatives from ambiguity to a working roadmap, alongside hands-on proficiency with AI coding agents.

Ready to apply?

The application is on the official Upside careers page.

Apply on company site