How Rubie replaced founder-managed billing with an automated contract-to-cash operation, saving 20 hours per month
Sales led
Finance
Accounting
Operations
C-suite
Automated invoicing
Intelligent collections
Real-time cash flow analytics
Edge-case escalations
Metrics reporting
About Rubie
Rubie is an AI-powered data migration platform that helps software companies win more deals by offering zero-effort customer migrations. Through its fleet of intelligent extraction, mapping, transformation, and validation agents, Rubie enables businesses to migrate customer data from any legacy system or source at a fraction of the time and cost of traditional approaches, turning competitor migrations into a competitive advantage.
Results:
Overview
Rubie, a leader in AI-powered data migration, built its product to automate the most tedious and complex processes in software onboarding. Behind the scenes, their CEO was personally creating invoices, chasing payments, and reconciling accounts. The team at Rubie partnered with Monk to bring that same automation-first philosophy to their entire billing operation, from the moment a contract is signed to the moment cash hits the bank and is reconciled.
Rubie was helping its customers eliminate manual, error-prone data workflows, yet their own billing operations were running entirely on founder time. Rubie's CEO was personally creating invoices, chasing down payments, and reconciling accounts, time that could have been spent on product, customers, and growth. There was no system connecting signed contracts to billing, no automated outreach for collections, and no clean way to track what had been paid and what hadn't. As Rubie's customer base grew, the strain compounded and the team recognized that their revenue operations needed the same transformation they were delivering to their own customers.
Challenge
The challenges were apparent for Rubie:
- No contract-to-invoice automation: There was no connection between a signed contract and the billing process. Invoicing schedules had to be manually interpreted and created from scratch for every customer, introducing delays and inconsistencies from the start of every engagement.
- Manual invoice delivery: Every invoice was sent by hand, with no standardized process, no tracking, and no guarantee of timely delivery across a growing customer base.
- Manual collections follow-up: With no automated outreach in place, the team was personally tracking outstanding invoices and sending individual follow-ups, creating an unpredictable and time-consuming collections process.
- Manual payment reconciliation: Matching incoming payments to open invoices required hands-on work and consumed significant time, making it difficult to maintain an accurate, real-time view of the business.
- Founder time misallocated: With the CEO personally owning the invoicing and collections process, one of Rubie's most valuable resources was being spent on work that should have been fully automated, pulling focus away from product, strategy, and customer relationships.
Our Solution
Rubie deployed Monk's full contract-to-cash platform, replacing every manual step in their revenue operations with intelligent automation.
Contract Upload and Automated Invoicing Schedules: Rubie uploads signed contracts directly into Monk, which automatically parses billing terms and generates correct invoicing schedules for each customer.
Automated Invoice Delivery: Monk sends invoices on Rubie's behalf on the right schedule, to the right contacts, with no manual intervention required. Every invoice goes out accurately and on time, regardless of how many customers are in the system.
Intelligent Collections: Monk's collections agents handle all payment follow-up with personalized, automated outreach across Rubie's full invoice portfolio, ensuring outstanding balances are addressed consistently while minimizing the need to pull anyone on the team into the loop.
Smart Escalation Playbooks: Custom escalation workflows triggered by payment behavior and aging thresholds, with dynamic routing to ensure the right stakeholder is engaged at the right moment to resolve outstanding balances quickly.
Real-Time AR Visibility and Payment Reconciliation: Live dashboards give Rubie a single, accurate view of AR and collection performance at all times, with automated reconciliation replacing the manual process of matching payments to open invoices.
Rubie exists to prove that the most complex, manual processes can be automated without sacrificing quality or control. By partnering with Monk, Rubie's team got their time back, and the entire contract-to-cash process, from signed agreement to collected payment, runs on autopilot. Rubie saves 20+ hours per month across invoicing, collections, and reconciliation, and built a billing infrastructure capable of scaling alongside their rapidly growing customer base without ever needing to hire for it.
