# AI Enablement Lead at Upside

- Company: Upside
- What the company does: Earn every time you shop gas, grocery, or food with Upside's free top-rated app. Get cash back on everyday necessities, making your purchases more rewarding. Download and start earning today! Backed by Bessemer and General Catalyst.
- Company website: https://www.upside.com/
- Type: Startups (AI role)
- Level: Senior
- Location: Austin
- Work setup: Remote
- Pay: $200K to $220K base salary per year (USD)
- Posted: 2026-09-20
- Apply by: 2026-11-04
- Apply: https://jobs.ashbyhq.com/upside/3fcc7f81-5b10-4656-bf87-c051fd56f338
- Page: https://www.1752.vc/careers/jobs/upside-ai-enablement-lead/

## About the role

Individual AI gains don't compound on their own. Shared infrastructure does.

## What they're looking for

- 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
- 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

Tags: Engineering