How StartPlaying’s Ops Manager Transformed Financial Chaos into Clarity
Customer Stories
10 Min Read
TL;DR Results
10+ hours saved per month
20% less investor admin time
Month-end close reduced by 4 days
Audit-ready books every month
 | Gabriella (“Gabi”) manages operations at StartPlaying, the world’s largest gameplay community platform connecting players with professional Game Masters (GMs). As Business Operations Manager, Gabi oversees nearly everything except engineering and product development. That means finance, compliance, and investor relations often land on her plate, areas that became increasingly complex as the company scaled.
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Company Snapshot
StartPlaying is the world’s largest platform connecting players with professional Game Masters (GMs) for online TTRPG sessions. As a lean (9 person team), post-Seed marketplace scaling fast, finance, compliance, and investor comms sat with operations, and with Gabi.
The Challenge: Marketplace Accounting + Manual Close
Gabi owned every aspect of operations including finance. And as the company grew, so did the complexity.
The pain points were classic marketplace problems:
Stripe (Connect) complexity: platform fees, GM payouts, refunds, disputes, and timing differences hitting Stripe balance vs. bank cash
Revenue recognition: separating gross bookings, platform take rate, and GM pass-through while tracking deferred revenue for prepaid sessions and gift credits
Month-end sprawl: CSV exports, pivot tables, and triple-checking to ensure nothing slipped through the cracks
Investor reporting debt: every month meant hours stitching KPIs and financials into an email + deck
“Before Truewind, our biggest challenge was making sure everything was fully accounted for at month-end," Gabi said. "With so many moving parts, it always felt like something could slip through the cracks. It made the close process stressful and time-consuming. I'd end up triple-checking everything just to be sure it was right."
StartPlaying needed reliable, accurate financials that could scale with the company without adding a full accounting team.
Why StartPlaying Chose Truewind
After evaluating Pilot, Botkeeper, and Zeni, Gabi chose Truewind for one simple reason: it didn’t just do bookkeeping, it made finance run like a system.
Truewind offered:
Proactive bookkeeping that flags issues early
Reliable, investor-ready reports each month
Real-time collaboration directly in Slack
Day-to-day impact: freeing up hours
“It’s really taken a lot off our plate,” Gabi shared. “We used to spend a ton of time chasing down details and reconciling things manually, but now everything feels structured and predictable.
Our back-office finance runs like a system instead of a scramble. It’s freed us up to focus on analysis and decision-making instead of just keeping up with the close.”
What Truewind Automated for StartPlaying
Before: Gabi spent hours categorizing transactions and reconciling Stripe payments manually.
After: Truewind’s AI Bookkeeping now does it automatically - income, expenses, and payouts are always clean and categorized.
Before: Closing the books took a week of late nights.
After: Every task lives in a shared checklist, cutting close time from 7 days to 3.
Before: Investor decks were built from scratch each month.
After: Truewind generates a polished reporting pack - P&L, cash flow, KPIs in minutes.
Who This Works For
Marketplaces using Stripe/Stripe Connect
Lean teams where Ops own finance
Post-Seed to series A companies needing investor-ready, audit-friendly books
FAQs
How does AI bookkeeping handle Stripe marketplaces?
Truewind’s AI parses Stripe Connect events to separate platform revenue, fees, disputes, and pass-through payouts to sellers/GM accounts, then reconciles against bank activity daily.
Can Truewind shorten our month-end close?
Yes. Teams typically reduce close by 3–5 days via automated reconciliations, checklists, and variance explanations.
Will this help with investor updates?
Yes. The Investor Reporting Pack exports board-ready P&L, cash bridge, and KPI slides, reducing investor admin time by ~20%
If I had to describe Truewind in one word: Lifechanging
— Gabriella, Business Operations Manager, StartPlaying
Ready to turn your finance chaos into clarity? Book a demo with Truewind today!
