Lead AI Product Manager, Merchant Platform

CWILL; Illinois; On-site; USD 150,000 - 200,000; Full time

Benefits offered by this job

401(k)

PTO

Paid Holidays

Insurance

Job summary

CWILL is seeking its first US-based platform PM to turn platform capabilities into a usable merchant experience for US Shopify merchants. You’ll define cross-product journeys, design AI Agent use cases, and help shape GTM strategy while partnering with Sales and CS.

You’ll own end-to-end platform design across multiple CWILL products, specifying AI agent tasks, onboarding, and how success is measured, with collaboration across a distributed team.

Qualifications

• 5-8 years of product experience, with 2+ years building AI or LLM-powered products from 0 to 1.
• Background in B2B SaaS — multi-product customer platforms (Customer 360, workflow automation, unified inbox, CRM, cross-product journeys, or AI copilot/assistant features).
• Proven ability to do real customer discovery: talking to merchants, running pilots, and turning ambiguous feedback into a clear roadmap.
• Fluent in AI application product design — agent task definition, tool calling, human-in-the-loop flows, trust and explainability.
• Comfortable working across time zones with a distributed engineering team; strong written communication.
• Heavy user of AI tools (GPT, Claude, Gemini, etc.).

Responsibilities

• Go deep with US mid-market Shopify merchants to understand why they run multiple tools in parallel, which workflows are still manual, and where they'd actually trust an AI Agent to act autonomously.
• Spend time with Sales and CS, validate use cases with real lighthouse customers before building.
• Design end-to-end customer journeys that span multiple CWILL products — for example: shipment delay → support escalation → compensation → review recovery, or VIP churn risk → marketing suppression → human outreach.
• Own the unified platform experience: information architecture, navigation, cross-product workflow design.
• Define what the AI Agent should do, what it should surface for human review, and how merchants understand what happened and why.
• Define Agent tasks, tool-calling scope, user permission and approval flows, error handling, and human escalation logic.
• Design the merchant-facing onboarding experience for AI features; set the bar for what "the Agent completed the task successfully" actually means.
• Communicate clearly to the engineering team: we're not building another chat interface — we're building an Agent that completes a measurable merchant task.
• Own platform packaging and pricing decisions: what's included in base plans, what belongs in higher tiers, and how to sell a suite instead of individual apps.
• Define the Lighthouse Customer program and expansion ARR playbook
• Partner with Sales and CS to drive cross-product attach rate
• Translate fuzzy merchant problems into crisp platform capability requirements the engineering team can build against
• Co-own prioritization decisions — not by escalating, but by building shared judgment on what's a real customer problem vs. a nice-to-have
• Reduce information loss across time zones through clear written specs and documented decisions

Skills

Product management

AI product design

Customer discovery

Cross-product design

Written communication

GTM strategy

Tools

GPT

Claude

Gemini

Job description

CWILL is seeking its first US-based platform PM to turn platform capabilities into a usable merchant experience for US Shopify merchants. You’ll define cross-product journeys, design AI Agent use cases, and help shape GTM strategy while partnering with Sales and CS.

You’ll own end-to-end platform design across multiple CWILL products, specifying AI agent tasks, onboarding, and how success is measured, with collaboration across a distributed team.