AI Enablement Lead

Meet Upside:

We created Upside to transform brick-and-mortar commerce. Our technology uses the sophistication of online retail—profit measurement, attribution, and incrementality to provide users with more value on their everyday purchases and brick-and-mortar businesses with new, profitable customers. We’ve helped millions of users earn 2 to 3 times more cashback than any other product, and hundreds of thousands of brick-and-mortar businesses earn measurable profit.

Billions of dollars in commerce run through the Upside platform every year, and that value goes directly back to our retailer partners, the consumers they serve, and important sustainability initiatives.

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

Every company right now is watching employees get faster with AI, one person and one workaround at a time. That's real, but it doesn't add up to anything durable: the gains stay locked in whoever figured out the trick, and the next person starts from zero. The organizations that pull ahead won't be the ones with the most individual AI users.

They'll be the ones that turned individual AI use into shared infrastructure: connected systems, encoded company knowledge, a marketplace of reusable skills (packaged AI capabilities people can install and reuse instead of rebuilding from scratch), and workflows that get smarter the more people use them.

Upside is building that infrastructure. It's called Ascent: a shared layer of connections, encoded company knowledge, and tooling that sits on top of Claude Enterprise, so that getting value from AI doesn't require every employee to build their own one‑off setup. Ascent already has a track record. It's the platform behind Upside's engineering org shipping 8‑week projects in 3, doubling our historical PR throughput and institutionalizing spec‑driven‑development org‑wide.

The same infrastructure is now being extended so the rest of the company, not just engineers, can get that kind of leverage.

The AI Enablement Lead owns Ascent's roadmap end to end, spanning both the engineering‑facing half (Software Factory, a program of tools and workflows purpose‑built for how engineers ship code) and the company‑wide half (the Enterprise Track, the same kind of AI leverage rebuilt for everyone else at Upside, regardless of technical background). The job is translating a fast‑moving, technical, still‑being‑invented platform into sequenced priorities, clear specs, and decisions the business can act on.

This role reports directly to the VP of R&D Intelligence, Systems and Enablement (RISE).

Upside's AI enablement work is making a transition that most companies haven't started yet: from point solutions to platform investment.

Point‑solution AI adoption looks like progress: more people using Claude, more one‑off skills, more individual productivity wins. But it plateaus. It doesn't compound, it's not repeatable across teams, and nobody can tell you what it's actually worth. Platform investment is different. It requires someone to hold the whole roadmap in their head, make sequencing calls across programs with different maturity levels, and be accountable for whether the infrastructure is actually working, not just whether people like it.

That's a materially different job than the ad hoc coordination that got Ascent this far. It needs a real owner: someone who can sit across two programs at different stages of maturity, make prioritization calls that hold up under scrutiny, and keep the roadmap coherent as the platform (and the underlying AI tooling itself) keeps changing under it.

These are the bets this role will drive. Ascent is mid‑build on both programs it contains; treat…