Lead Product Manager (SaaS & AI Agent)

CWILL; California (MO); 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 partner directly with the CEO. You will own cross-product platform design, define the AI Agent tasks, and shape how merchants experience and trust automated actions across multiple CWILL products.

You’ll work with Sales and CS, validate use cases with lighthouse customers, and drive GTM packaging and pricing decisions while coordinating with an distributed engineering team. This is a high-visibility, 0-to-1 role.

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 platforms (Customer 360, workflow automation, unified inbox, CRM)
• Proven ability to conduct real customer discovery with merchants
• Fluent in AI application product design — agent tasks, tool calling, human-in-the-loop flows
• Comfortable working across time zones with distributed engineering teams; strong written communication
• Heavy user of AI tools (GPT, Claude, Gemini) as a working style

Responsibilities

• Define end-to-end customer journeys spanning multiple CWILL products.
• Own unified platform experience: information architecture, navigation, cross-product workflows.
• Define and design AI Agent tasks, tool calling scope, human approval flows, error handling.
• Design onboarding for AI features; set criteria for task completion by the Agent.
• Collaborate on GTM, pricing decisions, and lighthouse customer program.
• Translate merchant problems into platform capability requirements for engineering.

Skills

Product management

AI product design

Customer discovery

Cross-product design

Written communication

Job description

About The Role

This is CWILL's first US-based platform PM, and it's a P0 hire that reports directly to the CEO.

What You’ll Do

Customer Discovery

• Go deep with US mid-market Shopify merchants — 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, not just in internal meetings; validate use cases with real lighthouse customers before building

Cross-Product Platform Design

• 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

AI Agent Product

• 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

GTM & Commercialization

• 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

Engineering Partnership

• 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

Requirements

What We’re Looking For

• 5-8 years of product experience, with 2+ years building AI or LLM-powered products from 0 to 1
• Background in B2B SaaS — ideally 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 — without needing to build the underlying model infrastructure
• Comfortable working across time zones with a distributed engineering team; able to reduce coordination overhead through strong written communication
• Heavy user of AI tools (GPT, Claude, Gemini, etc.) — not as a technical requirement, but as a working style

Nice to Have

• Experience in the Shopify / DTC ecommerce ecosystem (Klaviyo, Yotpo, Aftership, Loop, Narvar, or similar)
• Seller perspective — has run an online store or worked directly with ecommerce merchants
• MarTech or post-purchase SaaS background (marketing, support, reviews, retention)
• End-to-end B2B AI Agent product launch experience

Who You Are

• Startup mindset — you’re comfortable making decisions with incomplete information and iterating fast
• You think in customer outcomes, not feature lists
• You’d rather spend a day with a merchant than a week writing specs no one’s validated
• Big company or startup background doesn’t matter — ability and judgment do

Benefits

Starting Pay: 150K-200K depends on experiences, open to negotiation

• 401(k)
• PTO
• Paid Holidays
• Insurance