HappyRobot: Transforming Billing in 30 Days

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.

15 mins

Billing cycle (from 5-7 days)

$72.5K

Overages recovered in 30 days

60 hrs/mo

Staff time saved through automation
ABOUT THE COMPANY
HappyRobot
HappyRobot is an enterprise platform that builds, deploys, and monitors AI “workers” to automate communication tasks at scale.
HEADQUARTERS
San Francisco, California
INDUSTRY
Computer Software
COMPANY STAGE
Growth Stage

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

NameHappyRobot, Inc.
HQSan Francisco
IndustryAI Workers
StackSalesforce, 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

PhaseWhat We DidTime to Value
Kick-off (Day 0)Connected DocuSign & Stripe; ingested 14 months of historical contracts15 min
Audit (Days 1–3)Ari parsed every PDF, mapped SKUs, and reconciled 1,240 historical invoices; flagged $92 k in missing charges3 days
Automation Go-Live (Day 4)Slack approval flow for new contracts; automatic Stripe invoice scheduling and usage pulls via single endpointImmediate
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. 3–4 months of engineering.
  • Flexibility: Handles ad-hoc price breaks & tier bumps without schema changes — a previous blocker for HappyRobot.
  • Ownership: Data stays in HappyRobot’s Stripe account — no vendor lock-in.

Results After 30 Days

MetricBeforeAfter AriImpact
Monthly overage capture$0 (manual lag)$72.5 k+ 12 % MRR recovered
Invoice error rate7 per month0– 100 % mistakes
Billing cycle time5–7 days< 15 min5× faster
FTE hours on billing60 h/mo0 h/mo100 % improvement
Planned engineer hire10$150 k 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: Positive ROI in 30 days and >$150 k/year saved.
  • 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.
GET STARTED
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See how LedgerUp brings your billing and revenue systems into one place so you can remove busywork and focus on growth.