Pilot Success & Pipeline Ops Apprentice

Pilot Success & Pipeline Ops Apprentice (6-Month Cohort)

We just opened 1 FREE seat for a Pilot Success & Pipeline Ops Apprentice.
*FREE = costs you nothing, pays you in skills, tools, a production-grade portfolio, and a pathway to a paid Customer Success/RevOps role – not cash.

The Deal (Read Carefully)

This is a 6-month, intensive apprenticeship for hyper-organized operators who want to learn how early-stage SaaS companies acquire and retain their first customers. We do not pay you in cash; we pay you in leverage. You will be the operational shield for our CEO, managing the exact systems we are using to scale to $1M ARR. We provide the tools, the architecture, the senior mentorship, and the references. You provide the execution.

The Non-Negotiables:

• Time Commitment: 40 hrs/week. Can be negotiated under special circumstances to 20hrs/week.
• Exclusivity: You cannot hold another job, run a side-hustle, or be enrolled in university while doing this. You must be entirely focused.
• Location: US, Canada, or LATAM only.
• The Standard: This is not a hand-holding internship where you fetch coffee. You will be actively managing our actual pilot customers in Slack and managing live sales pipeline data for our Founder.

The Mission

Your goal is to ensure our pilot customers get massive value from Unstuck Engine, while ensuring no sales lead falls through the cracks. You will act as the "Concierge" for our early adopters, QA their data, answer their questions, and simultaneously triage our Founder's inbound sales pipeline generated by his continuous daily outbound marketing.

Background And Skills

You do not need a business degree, but you must have obsessive attention to detail and zero fear of talking to B2B customers. You must have extremely high emotional intelligence (EQ) in written communication (Slack/Email). You need to be deeply organized, capable of managing CRM data without making errors, and comfortable recording quick Loom videos to clearly explain concepts.

Daily Operations

• The Pilot Concierge: Manage the private Slack Connect channels for our pilot customers. Ensure their daily Unstuck data is delivered correctly, answer their basic questions, and schedule their check-in calls with our CEO.
• Pipeline Triage: Monitor the CEO’s inbound channels (LinkedIn DMs/comments, email replies). Filter out the noise, log qualified leads into the CRM, and draft replies for the CEO to approve.
• Data QA: Perform a daily manual "sanity check" on the intent data generated by Unstuck before it is passed to our customers, ensuring formatting and quality are pristine.
• The Documentation Engine: Every time a pilot customer asks a question, answer it—then instantly turn that answer into a permanent Notion wiki page and a Loom tutorial. You will build our V1 Help Center from scratch.

The Upside (Your Career Path)

This apprenticeship builds the exact hybrid Customer Success and Revenue Operations skills that early-stage startups desperately need. If you survive these 6 months, you walk away with the resume, title, and portfolio to land one of these roles:

1. Customer Success Manager
   Onboarding and retaining SaaS customers
   → $65K – $85K
2. RevOps Specialist
   Managing CRM data and sales pipeline flow
   → $70K – $90K
3. Founder's Associate
   Chief of Staff operations for early-stage CEOs
   → $75K – $95K

How To Apply

Submit your LinkedIn profile/resume and a short 1-minute intro video (Loom or similar) telling us why you are obsessed with organization and customer experience. If you pass the initial screen, our HR team will send you a specific, asynchronous technical task. Pass the task, and you go straight to a final interview with our CEO.