AI Platform Strategy Lead

Upside; Austin, Washington, New York, Chicago (TX, District of Columbia, NY, IL); Hybrid; USD 200,000 - 220,000; Full time

Benefits offered by this job

Health insurance

Equity (ISOs)

401(k) program

Parental leave

Wellness programs

Learning & Development stipend

Flexible work environment

Lunch reimbursement

Job summary

Upside is building Ascent, a shared layer of AI infrastructure to empower engineers and non‑technical staff alike. The AI Enablement Lead will own the end‑to‑end roadmap, balancing Software Factory and Enterprise Track priorities, and make sequencing trade‑offs that maximize business impact.

This role writes clear specs, defines measurable milestones, and partners with engineering to ship value. You will stay hands-on with AI tooling and communicate progress to executives and stakeholders.

Qualifications

• 5–8 years leading platform-level initiatives from ambiguity to a roadmap.
• Hands-on experience building with AI coding agents and dev tooling.
• Ability to write specs and drive prioritization across a technical program.
• Strong written and verbal communication to translate tech for executives.

Responsibilities

• Own the full Ascent roadmap across Software Factory and Enterprise Track.
• Write specs and requirements clear enough for engineering teams to execute.
• Track and report Ascent's maturity across core capabilities.
• Represent Ascent to stakeholders outside RISE with non-technical language.
• Stay current with AI coding/agent tooling landscape to inform the roadmap.

Skills

Roadmap prioritization

AI coding agents experience

Specs writing

Cross-functional collaboration

Executive communication

Tools

AI development tooling

Job description

Upside is building Ascent, a shared layer of AI infrastructure to empower engineers and non‑technical staff alike. The AI Enablement Lead will own the end‑to‑end roadmap, balancing Software Factory and Enterprise Track priorities, and make sequencing trade‑offs that maximize business impact.

This role writes clear specs, defines measurable milestones, and partners with engineering to ship value. You will stay hands-on with AI tooling and communicate progress to executives and stakeholders.