Operator; Retail

Data Drone builds 0-1 SaaS products and the team that ships them. No bosses, no managers — the playbook manages, the copilot tracks. Every role owns a small, defined space with extreme accountability. Small businesses sign up, activate, and start getting value without a sales call. The product does the heavy lifting. But behind the self-serve experience, someone makes sure no customer falls through the cracks.

You ll own the full retail customer lifecycle. Demos for interested prospects. Edge-case onboarding support when the self-serve flow doesn t cover it. Churn signal response when a customer is slipping. Product friction reporting when you see the same issue three times. You re the human layer on top of a well-automated system — handling the 10% that requires judgment, empathy, or a voice.

• Daily: scan the pipeline and health signals — demo requests through conversion, at-risk customers slipping.
• Within 48 hours: deliver personalized demos for prospect requests.
• Within 24 hours: respond to escalated retail churn signals.
• Per stuck customer: handle escalated onboarding support — and log the pattern, not just the fix.
• Monthly: surface product friction patterns to the Product Manager and flag retail customers ready to upgrade to enterprise.

• Deliver personalized demos within 48 hours of prospect request
• Manage the retail pipeline — demo requests through conversion
• Handle escalated onboarding support for self-serve customers who get stuck
• Respond to escalated retail churn signals within 24 hours
• Surface product friction patterns to the Product Manager monthly
• Identify retail customers who outgrow retail and should upgrade to enterprise
• Maintain retail playbooks (retail sales, onboarding, and success sections)

• You  worked with self-serve SaaS customers. Not just enterprise — the high-volume, low-touch segment where automation does most of the work and you handle the exceptions.
• You can deliver a product demo personalized to the prospect  industry in under 20 minutes.
• You can spot patterns. When the same support issue appears 3 times, you recognize it as a system problem, not 3 separate incidents.
• You can handle churn conversations. Not every customer should be saved. Knowing the difference — and handling both with professionalism — is the skill.
• You maintain a CRM. Pipeline clean, every interaction logged, no prospects in limbo.
• You communicate clearly in writing. Friction reports, demo follow-ups, churn documentation — concise and useful.

• Experience with local business or SMB SaaS
• Experience with CRM-automated customer journeys (you understand what the automation does so you can handle what it  n )
• Experience with product feedback loops — translating customer support into product improvements
• Comfort with AI copilots for demo prep and customer communication

• The automation handles 90%. You handle the 10% that matters most. The easy cases resolve themselves. The hard ones — the frustrated customer, the payment failure that needs a call, the cancellation that might be saved — that  where your value shows.
• Every support interaction is product feedback. A customer who can  complete onboarding isn t a support ticket. They  telling you something the product failed to communicate. Fix the issue AND log the pattern.
• Retail matters. It  not the “small” side of the business. It  the volume engine. Self-serve compounds. You re the quality layer that keeps it compounding.
• Personalize, don t template. Different business types have different workflows. The demo, the support, the check-in — each one is specific to their business.
• Clean cancellations have value. The reason someone leaves is data.…