Customer Success Lead
Listed on 2026-02-15
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IT/Tech
A Note From The Founder
Fair warning: this role starts neither glamorous nor strategic. Your first few months will be a lot of grunt work: auditing notes, cleaning up messy spreadsheets, and manually mapping workflows. You will build the CS operational foundation from scratch.
About ProbookProbook is the AI dispatcher for the home services industry, transforming how plumbing, HVAC, and electrical businesses operate.
Our impact is real. Dispatching the right technician to the right job can mean the difference between a $300 band-aid fix and a $20,000 system replacement. By automating proactive communication and around-the-clock workflows, Probook ensures a consistent customer experience without the need for 24/7 manual staffing. We unify these processes into a single, scalable platform, giving businesses one place to run their entire dispatch operation.
TheMandate
The Clean Sweep :
We have a $10M book of business that needs a forensic audit. You will reconcile every existing customer, ensuring health scores match reality and plans are in place. You will fix the manual workarounds our team is currently relying on.
The Deployment Factory:
You will cut our Time-to-Value drastically. You will shape the definitive Implementation Playbook, operationalizing the Pre-Flight Checklists that ensure every customer receives a white glove onboarding experience.
CS Intelligence:
You will provide a Single Source of Truth . You’ll own the CS tech stack and build the dashboards that tell us who is going to churn before it happens.
Revenue Leverage:
You will operationalize the renewal path. Automate the notification workflows and operationalize the Value Reports our teams need to close expansions.
Willing to Do Grunt Work:
You will personally wrangle messy documents, manually audit disjointed data, and chase clients for open invoices while you build the automation to replace yourself. You understand that you can’t automate a process you haven’t personally suffered through.Safe Hands for Sophisticated Work:
We can hand you a complex, high-stakes migration for a 1,000-technician enterprise client and trust it will be handled perfectly. You can toggle between the database and presenting a churn analysis to the Board.A Process Architect:
You hate doing the same manual task twice. You build structure as a reflex. You see operational drag and design the workflow to eliminate it.Technically Empathetic:
You understand the blue-collar reality of our users. You can translate a technician's frustration into a specific product bug or process gap.
2-5 years in high-agency roles: CS Ops, Implementation, COS, revops or Strategy at high-growth B2B SaaS (Seed to Series C)
Data Fluency:
Dangerous in Excel/SheetsNYC Based:
Excited to work 6 days/week in-office. We move too fast for remote work
Founding Role:
First operations hire. Build systems from scratch with zero bureaucracy and direct CEO access.The Market: $700B industry with clear tailwinds—AI adoption, labor shortages, generational transitions. We're defining the category, not fighting for share.
The Traction: $10M ARR in 18 months. Cash-flow positive. Product-market fit proven; now we're scaling.
The Backing:
Sequoia and a16z—partners who back category-defining companies.The Upside:
Meaningful equity in a company that controls its own destiny.
Equity:
Meaningful equity as a founding member of the operations team.Salary: 150K - 200K (depending on experience)
Health:
Comprehensive medical, dental, and vision.Perks:
Monthly stipend uber, food, gym, etc and unlimited office snacks.Access:
Direct access to world-class investors and advisors.
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