AI Enablement Lead
About the role
Upside is building a shared AI infrastructure called Ascent, a layer of connections, encoded company knowledge, and tooling that sits on top of Claude Enterprise. The AI Enablement Lead owns Ascent’s roadmap end‑to‑end, spanning the engineering‑focused Software Factory program 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).
Key Initiatives
- Own the Full‑Ascent Roadmap, prioritizing and sequencing work across both the Software Factory and Enterprise Track programs.
- Close the Enterprise Track’s maturity gap by defining “good enough” milestones for connectivity, Upside‑native knowledge, marketplace functionality, smarter tools, automation, and safe AI‑assisted building.
- Build a feedback loop that ties Ascent usage and AI spend to concrete business value through instrumentation, reporting, and valuation models.
Ongoing Responsibilities
- Partner with Ascent engineering teams as a product owner: own the roadmap, specs, and prioritization while they handle technical execution.
- Maintain and communicate the Ascent roadmap, ensuring coherent sequencing and trade‑off decisions across both programs.
- Write clear specifications and requirements that enable engineering teams to deliver without direct supervision.
- Track and report on Ascent’s maturity across its core capabilities, using data to justify future investments.
- Represent Ascent to stakeholders outside RISE, translating technical details into language that resonates with non‑technical audiences.
- Stay current with AI coding/agent tooling to ensure the roadmap reflects real‑world 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, with the ability to identify where off‑the‑shelf tools break down.
- Comfort building working, code‑based prototypes using AI coding agents (not required to ship production code, but must be able to prototype).
- Proven 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 fast‑changing technical concepts to engineers and executives.
- A “first‑hire” mindset, comfortable establishing roadmap and operating rhythm for a role without an existing template.
Preferred Qualifications
- Experience in AI/developer‑tools product management, such as internal platforms, dev‑experience tooling, or AI‑enablement products.
- Track record partnering across teams with differing technical and organizational maturity levels.
- Familiarity with adoption and enablement motions (rollout, communications, training), even if not the primary owner of those activities.
- Background in a scaling tech company where the role’s function was still being defined.
Location & Schedule
This hybrid role is based in one of Upside’s offices in Austin, Chicago, Washington, DC, or New York City. In‑office attendance is required on Monday, Tuesday, and Thursday, with the possibility of additional days based on project needs and evolving office policies.
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 (Incentive Stock Options)
- 401(k) retirement program
- Family planning programs and paid parental leave
- Physical fitness and wellness memberships
- Emotional and mental health support programs
- Unlimited PTO, 10 paid federal holidays, and an annual week‑long Winter Break
- Flexible work environment with lunch reimbursement for in‑office employees
- Employee Resource Groups
- Learning and Development stipend
- Transparent culture and a mission‑driven workplace