SlipstreamJobs tracks this role from the company's public career site. Apply directly on the employer's site.
Salary: USD 200,000 - 220,000 / annual
Upside is transforming brick-and-mortar commerce by providing cashback and loyalty solutions to consumers and profitable customer acquisition to retailers. The company is now building Ascent, a shared AI infrastructure platform that turns individual AI productivity gains into company-wide, reusable systems.
The AI Enablement Lead owns Ascent's end-to-end roadmap, spanning two programs: Software Factory (engineering-focused AI tooling that has already demonstrated impact—8-week projects shipped in 3 weeks, doubled PR throughput) and the Enterprise Track (bringing the same AI leverage to non-technical teams across the company). This role reports to the VP of R&D Intelligence, Systems and Enablement.
The core challenge: most companies are stuck in point-solution AI adoption (individual productivity wins that don't compound). Upside is transitioning to platform investment, which requires a single owner to hold the full roadmap, make sequencing trade-offs across programs at different maturity levels, and be accountable for whether the infrastructure actually drives business value.
Key responsibilities include:
- Own prioritization and sequencing across both Software Factory and Enterprise Track, making real trade-off calls on shared infrastructure investment
- Close the Enterprise Track's maturity gap by deciding which of six core capabilities (connected systems, Upside-native knowledge, marketplace, gets-smarter feedback, automation, safe AI-driven development) to invest in first
- Build the feedback loop connecting Ascent usage to business value: instrumentation, reporting, and a working model of skill/agent ROI so roadmap decisions are evidence-driven, not opinion-driven
- Partner with dedicated engineering teams as a product owner (no direct reports; influence comes from spec quality and credibility of calls)
- Write clear specs and requirements for engineering teams you don't manage
- Track and report on Ascent's maturity across core capabilities
- Represent Ascent to non-technical stakeholders, translating technical platform into business language
- Stay hands-on with the AI coding/agent tooling landscape to inform roadmap decisions
This is a first-hire-type role: the operating rhythm and roadmap structure are yours to define. The role requires comfort with ambiguity, platform-level thinking, and the ability to drive prioritization across technical programs without direct authority.
Requirements:
- 5–8 years leading platform-level or 0-to-1 initiatives from ambiguity to working roadmap (not isolated features or one-off projects)
- Deep, hands-on personal experience building with AI coding agents and AI dev tooling; must have felt where off-the-shelf tools break down and translated that friction into product judgment
- Ability to build working, code-based prototypes yourself using AI coding agents (not expected to ship production code, but must be able to sit down and get an agent to build a working prototype)
- Demonstrated ability to write specs and drive prioritization across technical programs without direct authority over builders
- Strong written and verbal communication; must translate fast-changing technical platform for audiences from engineers to executives
- First-hire mindset; comfortable building roadmap and operating rhythm for a role without a template
Strong plus:
- Experience in AI/developer-tools product management (internal platforms, dev experience tooling, AI-enablement products)
- Experience partnering across teams at different levels of technical and organizational maturity simultaneously
- Familiarity with adoption/enablement motions (rollout, comms, training)
- Background in scaling tech company where the role's function was still being defined
