High‑growth subscription companies often discover that the hardest part of scaling isn’t selling, it’s proving the revenue is accurate and complete in a form auditors accept and executives can trust. During our recent “Ledgers & Lagers” session, Jon Ashton of Healthie and Ben Liepman of AllTrails shared how they finally bent Stripe’s raw transaction fire‑hose into compliant, decision‑ready numbers.

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Below is a recap of their stories, the tactical wins they unlocked, and why every accounting and finance team should care.

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Jon’s Story: Three Businesses in One Stripe Account

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Healthie serves large enterprise medical groups, thousands of SMB clinics, and each clinic’s end‑patients, all riding through one Stripe instance. Contracts range from multi‑year, prepaid invoices to month‑to‑month self‑service plans, plus “connected accounts” that turn Healthie into an agent for patient charges.

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The headache: 

• Stripe Revenue Recognition couldn’t handle multi‑year enterprise contracts because the contract itself lives in Salesforce, not in Stripe.
• Fee transparency was nonexistent; Jon had to stitch multiple CSVs just to find the costs hidden behind each gross receipt.
• Millions of rows made Excel unusable; flux analysis or cohort views required hours of manual joins.
  
  

What changed

Implementing a purpose‑built sub‑ledger let Healthie merge Salesforce contracts, Stripe payments, and connected‑account settlements in one model. Jon now slices revenue by geography, cohort, or fee bucket instantly, and even tracks how many enterprise customers have been migrated off costly card rails to ACH each week.

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Impact

Better analytics translated into real organizational influence: Jon’s faster answers and cleaner reconciliations earned him a promotion after go‑live. It also surfaced duplicate or mis‑applied Stripe fees Healthie could claw back.

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Ben’s Story: Hundreds of Millions of Transactions—Lean Team, Many Rails

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AllTrails sells an outdoor hiking navigation app through Apple, Google Play, web (Recurly + Stripe/PayPal). It’s available in over 180 countries, meaning foreign exchange is a huge part of AllTrail’s close process. 

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The headaches: 

• Apple App Store, Google Play, Recurly, Stripe, and Paypal each provide different reporting formats, so a single subscription’s life had to be “triangulated” across storefront reports, gateways, and NetSuite imports.
• Dumping every event into NetSuite would explode licensing costs and still lack the columns FP&A wanted (e.g., geo, currency, platform).
• Stripe fees on fees (“Ticketmaster math”) obscured gross‑profit analysis until weeks after close.

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What changed
Ben moved transaction flow into a sub‑ledger that:

1. Captures platform fees and capitalizes them under ASC 340 so margin reporting lines up with the revenue waterfall.
2. Automates geo and currency tagging so executives finally see revenue by market in real time.
3. Flags fee anomalies—including that infamous “fee‑on‑fee”—before cash leaves the bank.

Impact
With daily, drill‑down reporting, AllTrails could test new pricing tiers (AllTrails Plus, AllTrails Peak) quickly and know within days—not months—whether the unit economics held. Accounting stopped being the bottleneck and started guiding product rollouts.

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Four Takeaways Every Subscription CFO Should Steal

1. Stripe Alone Is Not a Sub‑Ledger
   Its APIs are built for payment acceptance, not ASC 606. Relying on Stripe Revenue Recognition to split multi‑element contracts or agent/principal flows will leave gaps the audit team (or the board) will eventually find.
   
2. Granular Fee Visibility Pays for Itself
   Both companies exposed hidden or miscoded costs once fees were modeled per transaction rather than averaged across payouts.
   
3. Real‑Time Data Isn’t a Luxury When You Experiment Weekly
   Daily waterfalls let AllTrails’ finance team signal go/no‑go on new price plans while marketing still has momentum.
   
4. Career Equity Grows When Accounting Stops Copy‑Pasting CSVs
   Jon’s promotion underscores a truth: freeing accountants from reconciliation drudgery lets them become the people who answer the CEO’s toughest questions first.

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Why This Problem Is Worth Solving

Misstated revenue isn’t just an audit risk; it starves the business of credible metrics. When unit costs hide in opaque fee buckets and subscription cohorts blur together, decisions about product‑led growth, international rollout, or funding strategy are shot in the dark. Stripe, Apple, Google, and PayPal won’t change their schemas to match GAAP; the burden falls on accounting to translate operational events into accounting truth at scale.

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Healthie and AllTrails show that a deterministic sub‑ledger, one that ingests raw events, enriches them with contract data, and outputs journal‑ready entries, turns that burden into leverage:

• Faster closes free headcount without hiring.
• Clean cohorts let FP&A model LTV by geography or acquisition channel.
• Audit readiness stops being an annual fire‑drill.
  
  

In short, automating order‑to‑cash accounting is less about “modern tech stacks” and more about restoring trust—in the numbers, in the decisions drawn from them, and in the professionals behind those numbers.

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TL;DR:

Stripe’s flexibility has powered a generation of SaaS growth, but flexibility without structure breeds accounting chaos. Jon and Ben proved that taming the chaos unlocks not only smoother closes but stronger strategic voices for finance. Your ledger should be your loudest ally, not your slowest colleague. Time to give it the tools to speak.

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