AI Enablement Lead

We need to output HTML fragment with sections: About the role, Responsibilities, Requirements, Qualifications, Skills, Benefits, Pay, Schedule. Only include sections that have real specific content. Must not repeat job title. Must not include Job ID etc. Must remove boilerplate. Must preserve all substantive info. We need to parse the posting. Let's extract sections: - About the role: The description of the role, mission, opportunity, why role exists now, key initiatives, ongoing responsibilities. Could be under "About the role" or maybe "Responsibilities". The instruction: use

for section headings (e.g. About the role, Responsibilities, Requirements, Qualifications, Skills, Benefits, Pay, Schedule). So we need to decide which sections to include based on content. We have content about the role: "Meet Upside ... The Opportunity ... Why This Role Exists Now ... Key Initiatives ... Ongoing Responsibilities ...". That could be "About the role" (overview) and "Responsibilities". Also we have "Must Have What We're Looking For" (requirements/qualifications/skills). Also "Strong Plus ..." (preferred). Also location, compensation, benefits. We need to include sections only if they have real specific content. Let's map: - About the role: could contain the mission description, opportunity, why role exists now, key initiatives. That's substantive. - Responsibilities: we have "Ongoing Responsibilities" list bullet points. Also maybe "Own and maintain the Ascent roadmap..." etc. So we can put responsibilities. - Requirements: "Must Have What We're Looking For" list: 5-8 years leading platform-level..., deep hands-on personal experience building with AI coding agents..., comfort building working code-based prototypes..., demonstrated ability to write specs..., strong written and verbal communication..., "first-hire" mindset. Those are requirements. - Qualifications: maybe overlapping with requirements; but we could treat "Must Have" as Requirements, and "Strong Plus" as Qualifications or Skills. However we need to avoid duplication. Could put "Qualifications" for the "Strong Plus" items (preferred). Or we could put "Skills" for technical skills like AI coding agents, prototyping, spec writing, communication, etc. But we need to follow instruction: use sections only when posting has real specific content. We have content for Requirements (must have). We have content for Preferred qualifications (Strong Plus). We have content for Benefits (listed). We have content for Pay (Compensation range). We have content for Schedule (Location hybrid, in-office attendance required Monday, Tuesday, Thursday). Also maybe "Location" not a section but could be part of Schedule? The instruction only lists those headings; we can include Schedule for in-office days. Thus we will include sections: About the role, Responsibilities, Requirements, Qualifications (or Skills), Benefits, Pay, Schedule. We need to decide which heading for each. Let's assign: - About the role: overview (mission, opportunity, why role exists now, key initiatives). - Responsibilities: ongoing responsibilities bullet list. - Requirements: Must Have bullet list. - Qualifications: Strong Plus bullet list (preferred experience). Could also be Skills but Qualifications fits. - Benefits: list of benefits. - Pay: compensation range. - Schedule: location/hybrid in-office days. We must not include filler like "commensurate with experience". Not present. We must not include boilerplate like EEO etc. Remove Diversity and Inclusion, Notice to Recruiters, etc. We must preserve all substantive information: need to include details like the mission description, the opportunity text, why role exists now, key initiatives (own full-ascent roadmap, close enterprise track maturity gap, build feedback loop), ongoing responsibilities bullet points, must-have requirements, strong plus, benefits list, compensation range, schedule details. We need to format as HTML: use

for each section heading, then content:

for prose,

• for lists. We must not include any extra markup like or . Just the fragment. Let's craft. First, About the role: combine paragraphs. We need to preserve all substantive info: The mission: "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." Then Opportunity: "The Opportunity 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)." Then Why This Role Exists Now: paragraph. Then Key Initiatives: bullet list? It's prose but we can make list. We'll put as
  • for each initiative. Let's extract key initiatives: - Own the Full-Ascent Roadmap (description) - Close the Enterprise Track's Maturity Gap (description) - Build the Feedback Loop That Ties Ascent to Business Value (description) We'll keep the description. Now Responsibilities: Ongoing Responsibilities bullet list: - Partner with the teams building Ascent as a product owner partners with engineering: you own the roadmap, the specs, and the prioritization calls; they own technical execution and design. - Software Factory and the Enterprise Track each have their own dedicated engineering teams and their own managers. This role has no direct reports, and your influence comes from the quality of your specs and the credibility of your calls, not from authority over anyone's headcount. - Own and maintain the Ascent roadmap across both Software Factory and the Enterprise Track, and be the person accountable for its sequencing and trade-offs - Write specs and requirements clear enough that engineering teams you don't manage can execute against them without you in the room - Track and report on Ascent's maturity across its core capabilities, and use that to justify what gets invested in next - Represent Ascent to stakeholders outside RISE, explaining what it does, what it doesn't yet do, and what's coming, in language that lands with non-technical audiences - Stay current, hands-on, with the AI coding/agent tooling landscape so the roadmap reflects real friction and real capability, not secondhand reports of it. We'll put each as
  • . Now Requirements (Must Have): - 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 - Deep, hands-on personal experience building with AI coding agents and AI dev tooling: enough to have felt where off-the-shelf tools break down and turned that friction into product judgment. This isn't optional context; it's the thing that makes the roadmap calls credible. - Comfort building working, code-based prototypes yourself using AI coding agents. You're not expected to ship production code, but if you can't sit down and get an agent to build you a working prototype, you won't be able to tell a real capability gap from a skill-issue complaint. - 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 Now Qualifications (Strong Plus): - Experience specifically in AI/developer-tools product management: internal platforms, dev experience tooling, or AI-enablement products - Experience partnering across teams at different levels of technical and organizational maturity at the same time - Familiarity with adoption/enablement motions (rollout, comms, training) even though this role isn't primarily responsible for driving them - Background in a scaling tech company where the role's function was still being defined Now Benefits: list: - Medical, dental, and vision coverage starting on Day 1 - Equity (ISOs) - 401(k) program - Family planning programs + paid parental leave - Physical fitness and wellness memberships - Emotional and mental health support programs - Unlimited PTO + 10 paid federal holidays + our annual, week-long Winter Break - Flexible work environment - Lunch reimbursement for in-office employees - Employee Resource Groups - Learning and Development stipend - Transparent culture - Amazing mission! We could keep as list. Now Pay: Compensation: "The U.S. base salary range for this full-time position is $200,000 - $220,000 + equity + benefits. The final starting pay will be determined based on job-related skills, experience, qualifications, work location, and market conditions. Your recruiter can share more about the specific salary range during the hiring process." We'll put that in

    . Now Schedule: Location/hybrid: "Location: This hybrid role is based in our Austin, Chicago, DC, or NYC office. In-office attendance is required on Monday, Tuesday, and Thursday and may increase based on project-based needs and changes to Upside’s in-office policy over time." We'll put that in

    . We must not include any other boilerplate like Diversity, Notice to Recruiters, etc. Now produce HTML. We'll start with

    About the role

    then paragraphs. We need to ensure we don't duplicate content. Let's craft. We'll combine About the role paragraphs into maybe two

    blocks: first mission/opportunity, second why role exists now and key initiatives? But we have separate sections for responsibilities etc. We'll keep About the role as overview: mission, opportunity, why role exists now, key initiatives. Let's write:

    Meet Upside ... (mission paragraph).

    The Opportunity ... (opportunity paragraph).

    Why This Role Exists Now ... (paragraph).

    Then maybe we can include Key Initiatives as a
    under About the role? But we could also put them under Responsibilities? No, they are initiatives the role will drive. Could be part of About the role. We'll include as
    after the why paragraph