Tech Operations Operator (Enterprise)

DataDrone Inc.; Cheyenne, Northern (WY, KY); Hybrid; USD 90,000 - 130,000; Full time

Job summary

DataDrone Inc. is seeking an operations-focused professional in Cheyenne, WY to own enterprise onboarding, provisioning, and billing workflows.

You will monitor automation triggers, validate data integrity, and ensure accurate handoffs between Sales, Onboarding, and the success team. You will document runbooks, monitor signals for reliability, and coordinate with non-technical stakeholders to keep deployments precise and scalable.

Qualifications

• Experience operating CRM-driven workflows for B2B accounts (provisioning, lifecycle management, billing).
• Ability to troubleshoot automation where it breaks, not just run it passively.
• Proficiency in validating data accuracy across multi-outlet accounts.
• Ability to read signal logic and verify trigger firing correctly.

Responsibilities

• Provision enterprise accounts (multi-outlet, multi-contact, custom billing).
• Operate and monitor onboarding automation — milestone triggers, stall detection, communication sequencing.
• Operate and monitor client success signals — usage dips, payment failures, health score accuracy.
• Validate technical handoffs — reject incomplete Sales → Onboarding handoffs with specifics.
• Manage enterprise billing operations — subscription status, billing accuracy.
• Maintain provisioning runbooks, onboarding automation docs, and signal documentation.

Skills

CRM-driven workflows

Automation troubleshooting

Data validation

Signal logic understanding

Runbook documentation

Cross-team communication

Tools

CRM software

Billing system

Automation tooling

Job description

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. For enterprise clients with 10, 25, or 50 outlets, the technical operations behind onboarding and retention are the difference between "great product" and "great experience".

What You'll Do

You'll own the technical operations that power the enterprise client lifecycle. When a 25-outlet deal signs, you provision every outlet. When onboarding automation fires milestone reminders, you configured and verified those triggers. When client success signals detect a usage dip at outlet #17, your instrumentation caught it. You're the operational layer between the systems (built by the Systems Builder) and the humans who serve enterprise clients.

Daily Rhythm (How You Operate)

• Daily: monitor onboarding automation and client success signals — milestone triggers firing, usage dips and payment failures surfacing accurately.
• Per deal: provision enterprise accounts (multi-outlet, multi-contact, custom billing) and validate every record before marking it done.
• At intake: validate Sales → Onboarding handoffs and reject incomplete ones with specifics.
• Weekly: reconcile billing accuracy and capacity plan against deals closing next month.
• Always: document your operational processes as runbooks — someone else can follow them if you're out.

Key Responsibilities

• Provision enterprise accounts (multi-outlet, multi-contact, custom billing terms)
• Operate and monitor onboarding automation — milestone triggers, stall detection, communication sequencing
• Operate and monitor client success signals — usage dips, payment failures, health score accuracy
• Validate technical handoffs — reject incomplete Sales → Onboarding handoffs with specifics
• Manage enterprise billing operations — subscription status, billing accuracy
• Maintain provisioning runbooks, onboarding automation docs, and signal documentation

What We're Looking For

• You've operated CRM-driven workflows for B2B accounts (provisioning, lifecycle management, billing).
• You understand automation workflows well enough to troubleshoot when they break — not just run them when they work.
• You can validate data accuracy. One wrong field on 25 outlets is 25 corrections. You catch it before it propagates.
• You can read signal logic (if usage < X for Y days → trigger intervention) and verify it's firing correctly.
• You document your operational processes. If you're unavailable, someone else can follow your runbook.
• You can work with non-technical operators. They depend on your systems. You communicate status and issues clearly.

Bonus Points For

• CRM experience (enterprise account management, multi-entity structures)
• Experience with subscription billing systems
• Experience with enterprise client onboarding (multi-location, multi-stakeholder)

The Mindset We Hire For

• Validate before you mark it done. Provisioning isn't done when the records are created — it's done when the validation checklist passes.
• Signals are only useful if they're accurate. A false alarm wastes the success team's time. A missed signal costs an account. Both are your failures.
• Reject incomplete handoffs. Accepting a handoff with missing technical requirements is accepting a stalled onboarding 3 weeks from now. Catch it at the door.
• Plan ahead. If 3 deals are closing next month, you should know the outlet count today. Reactive provisioning is panicked provisioning.
• Document as you operate. Runbooks are not "when I have time." They're part of the work.

Success in This Role

• 30 Days — Every enterprise account mapped. Provisioning workflow tested. Automation triggers audited. Operator relationships established.
• 60 Days — Runbooks complete. Automation verified. Signal accuracy tracked. Operators trust the systems.
• 90 Days — Zero client-facing errors. Automation runs autonomously. Signals are trusted. Capacity planning is proactive.

Why Join Us

You won't babysit systems that barely work. You'll operate enterprise infrastructure that's built properly and needs someone who runs it with precision. Every enterprise account depends on your provisioning accuracy, your trigger reliability, and your signal integrity. The work is operational and the impact is direct.

5 hours of focused operations per day. Precision over volume.

Self-Check Before You Apply

• When you provision 25 accounts, do you validate all 25 — or spot-check 5 and hope?
• When an automation fails, can you read the execution log and diagnose the failure without asking the person who built it?
• Do you catch data errors before they reach the client — or after the client reports them?
• Can you explain a signal threshold to a non-technical operator and have them understand when and why it fires?
• Is your operational documentation current — or "mostly right, I think"?
• When a handoff is missing information, do you reject it with specifics — or accept it and figure it out later?