HappyRobot Case Study: Transformed Billing in 30 Days
Apr 8, 2025
Within 30 days of deploying LedgerUp’s AI agent Ari, HappyRobot eliminated invoice errors, recovered $72.5 k in previously un‑billed overages, and avoided the $150 k+ annual cost of hiring a full‑time billing engineer.
Within 30 days of deploying LedgerUp’s AI agent Ari, HappyRobot eliminated 100 % of invoice errors, recovered $72.5 k in previously un‑billed overages, and avoided the $150 k+ annual cost of hiring a full‑time billing engineer. The team now spends <15 min/week (down from 15 hours) on contract‑to‑cash tasks, and to quote their team: “Ari is our new best friend.”Company Snapshot
Name | HappyRobot, Inc. |
HQ | San Francisco |
Industry | Voice‑AI infrastructure |
Stack | Salesforce, DocuSign, Stripe, Slack |
Challenges Before LedgerUp
Manual overage math: 50+ contracts each carried bespoke minute tiers; finance copied usage CSVs into spreadsheets and hand‑calculated overage invoices every month, leading to delays and errors.
Stripe hygiene issues: Legacy invoices, duplicate customers, and inconsistent metadata confused reporting and reconciliation.
Engineer hire on the table: Leadership budgeted for a mid‑level full‑stack engineer (~$150 k total comp in SF) to build an in‑house usage‑billing service.
Revenue leakage & audit risk: Usage‑based SaaS firms lose 5‑10 % of ARR to under‑billing when workflows stay manual.
Solution – Ari, the Contract‑to‑Cash Agent
Phase | What We Did | Time to Value |
|---|---|---|
Kick‑off (Day 0) | Connected DocuSign & Stripe; ingested 14 months of historical contracts | 15 min |
Audit (Days 1–3) | Ari parsed every PDF, mapped SKUs, and reconciled 1,240 historical invoices; flagged $92 k in missing charges | 3 days |
Automation Go‑Live (Day 4) | Slack approval flow for new contracts; automatic Stripe invoice scheduling and usage pulls via single endpoint | Immediate |
Overages (Day 12) | Ari began daily metered-usage checks; generates overage invoice and posts to Slack for 1‑click send | <2 weeks |
Why Ari Beat the “Build” Option
Speed: Production in <1 week vs. an estimated 3‑4 months of engineering time.
Flexibility: Handles ad‑hoc price breaks & tier bumps without schema changes—one of the blockers with SalesBricks noted by HappyRobot.
Ownership: Data stays in HappyRobot’s existing Stripe account—no secondary account or vendor lock‑in.
Results After 30 Days
Metric | Before | After Ari | Impact |
|---|---|---|---|
Monthly overage capture | $0 (manual lag) | $72.5 k | +12 % MRR recovered |
Invoice error rate | 7 per month | 0 | –100 % mistakes |
Billing cycle time | 5–7 days | < 15 min | 5× faster |
FTE hours on billing | 60 h/mo | 0 h/mo | 100% improvement |
Planned engineer hire | 1 | 0 | $150k saved |
“Ari took a job we dreaded and turned it into a Slack notification we look forward to. He’s literally our new best friend.”
— Varez, Go‑to‑Market Lead, HappyRobot
“We recouped an entire engineer’s salary before the first invoice cycle closed.”
— Quili Peña, Chief of Staff, HappyRobot
Looking Ahead
Salesforce field sync: Ari now populates ARR, minutes‑used, and overdue‑days directly into SFDC so leadership dashboards refresh in real time.
Global expansion: Madrid entity will mirror the U.S. flow without adding headcount.
Key Takeaways
Automation beats headcount – HappyRobot saw positive ROI in 30 days and saved >$150 k/year in payroll.
Start with the biggest leak – Overages were the fastest path to recovered revenue (12 % uplift).
Keep systems of record intact – By operating inside Stripe & Salesforce, Ari avoided the “second billing system” trap SalesBricks ran into.