Operator (Retail)

DataDrone Inc.; Cheyenne, Northern (WY, KY); Híbrido; USD 60.000 - 90.000; Jornada completa

Descripción de la vacante

DataDrone Inc. is seeking a high-velocity Customer Success professional to own the full retail customer lifecycle, from demo to onboarding and churn follow-ups. You will operate a self-serve SaaS model with a strong emphasis on rapid, personalized engagements, documenting patterns, and maintaining a clean CRM.

You will deliver demos, log activities, and collaborate with Product to identify friction points while ensuring customers remain engaged and successful across the lifecycle.

Formación

• Experience with high-volume, low-touch self-serve SaaS environments.
• Ability to deliver personalized product demos in under 20 minutes.
• Spot recurring issues to identify systemic patterns.
• Handle churn conversations with professionalism and tact.
• Maintain a clean CRM with complete interaction history.
• Communicate clearly in writing; provide concise friction reports.

Responsabilidades

• Deliver personalized demos within 48 hours of prospect requests.
• Manage the retail/demo pipeline from inquiry to conversion.
• Provide escalated onboarding support for self-serve customers.
• Respond to churn signals within 24 hours and document learnings.
• Surface product friction patterns to Product Manager monthly.
• Keep documentation and playbooks up to date for retail.

Conocimientos

Self-serve SaaS experience

Personalized demos

Pattern recognition

Churn handling

CRM management

Clear written communication

Herramientas

CRM

Analytics dashboard

Chatbot escalations

Video conferencing

Slack

Google Drive

AI copilot

Descripción del empleo

DataDrone 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.

What You\'ll Do

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 Rhythm (How You Operate)

• 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.

Key Responsibilities

• 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)

What We\'re Looking For

• You\u2019ve 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\u2019s 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.

Bonus Points For

• 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 \u2019doesn\u2019t)
• Experience with product feedback loops — translating customer support into product improvements
• Comfort with AI copilots for demo prep and customer communication

The Mindset We Hire For

• 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\u2019s where your value shows.
• Every support interaction is product feedback. A customer who can\u2019t complete onboarding isn\'t a support ticket. They\u2019re telling you something the product failed to communicate. Fix the issue AND log the pattern.
• Retail matters. It\u2019s not the “small” side of the business. It\u2019s 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. Document it. Feed it back. Don\'t just close the ticket.

Success in This Role

• 30 Days — Product used as a customer. Playbooks read. First demos delivered. Daily scan rhythm established.
• 60 Days — Demo conversion baselined. Churn signals handled within SLA. First friction report delivered.
• 90 Days — Retail metrics at target. Friction feedback pipeline running. Playbooks updated. Retail runs clean.

Tools You\’ll Use

CRM, analytics (health dashboard), chatbot escalations, video conferencing (demos), Slack, Google Drive, AI copilot.

Why Join Us

You won\’t manage a support queue. You\'ll own an entire customer lifecycle — from “I\’m interested” to “I\’ve been using this for a year.” The automation handles the routine. You handle the moments that shape whether a customer stays or goes, whether the product gets better or stagnates, whether retail grows or flatlines.

5 hours of focused work per day. High variety — demos, support, churn intervention, product feedback — no two days identical.

Self-Check Before You Apply

• Can you deliver a personalized product demo in under 20 minutes to a business type you\'ve never sold to before?
• When a self-serve customer can\’t figure something out, is your instinct “how do I fix this for everyone?” or just “how do I fix this for them?”
• Can you tell the difference between a cancellation you should save and one you should let go?
• Do you track patterns in support interactions — or treat each one as isolated?
• When was the last time your customer feedback directly changed a product feature?
• Can you manage 50+ retail accounts and a demo pipeline simultaneously without dropping anything?

If three or more are yes, that\’s you — apply.