AI Enablement Lead

Upside•Austin, TX

1d•$200,000 - $220,000•Hybrid

About The Position

Upside is building Ascent, a shared AI infrastructure layer that connects systems, encodes company knowledge, and provides a marketplace of reusable AI capabilities. This platform aims to transform individual AI gains into shared, compounding value for the organization. The AI Enablement Lead will own the end-to-end roadmap for Ascent, encompassing both the engineering-focused Software Factory and the company-wide Enterprise Track. This role involves translating technical platform development into actionable priorities, clear specifications, and business-driven decisions. The position reports directly to the VP of R&D Intelligence, Systems and Enablement (RISE). This role is crucial as Upside transitions from point-solution AI adoption to platform investment, requiring a dedicated owner to manage the roadmap, make prioritization calls, and ensure the infrastructure delivers tangible business value.

Requirements

5-8 years leading platform-level or 0-to-1 initiatives from ambiguity to a working roadmap, not just running isolated features or one-off projects.
Deep, hands-on personal experience building with AI coding agents and AI dev tooling: enough to have felt where off-the-shelf tools break down and turned that friction into product judgment.
Comfort building working, code-based prototypes yourself using AI coding agents.
Demonstrated ability to write specs and drive prioritization across a technical program without direct authority over the people building it.
Strong written and verbal communication: you'll be translating a fast-changing, technical platform for audiences ranging from engineers to executives.
A "first-hire" mindset: comfortable building the roadmap and the operating rhythm for a role that doesn't have a template yet.

Nice To Haves

Experience specifically in AI/developer-tools product management: internal platforms, dev experience tooling, or AI-enablement products.
Experience partnering across teams at different levels of technical and organizational maturity at the same time.
Familiarity with adoption/enablement motions (rollout, comms, training) even though this role isn't primarily responsible for driving them.
Background in a scaling tech company where the role's function was still being defined.

Responsibilities

Own and maintain the Ascent roadmap across both Software Factory and the Enterprise Track, and be the person accountable for its sequencing and trade-offs.
Write specs and requirements clear enough that engineering teams you don't manage can execute against them without you in the room.
Track and report on Ascent's maturity across its core capabilities, and use that to justify what gets invested in next.
Represent Ascent to stakeholders outside RISE, explaining what it does, what it doesn't yet do, and what's coming, in language that lands with non-technical audiences.
Stay current, hands-on, with the AI coding/agent tooling landscape so the roadmap reflects real friction and real capability, not secondhand reports of it.
Drive the roadmap that closes the maturity gap for the Enterprise Track, deciding which capability to invest in first, what "good enough" looks like at each stage, and how to prove out value.
Own building the feedback loop for Ascent: instrumentation, reporting, and a working model of what "this skill or agent is worth it" means, so that Ascent's roadmap is driven by evidence of what's working.