The challenge

When Richard Dennis joined Willo^® as CFO in January 2025, the revenue operations setup was held together by spreadsheets and manual effort.

The workflow looked like this: a seller closes a deal in HubSpot, which triggers a notification to a shared Excel spreadsheet. Someone on the finance team monitors that spreadsheet, picks up the new deal, manually creates the subscription in Stripe, provisions the account, and kicks off billing. For some contracts, invoicing happened in Xero instead of Stripe, which added another step. Metrics in ProfitWell had to be manually patched because certain Stripe actions weren't reflected automatically.

Five systems. No integrations. Manual input at every handoff.

"It was pretty quickly evident to me that it wasn't a process that was scalable at all," Richard said. "It would just require more heads to keep managing that manual process."

Contract amendments followed the same path. An upgrade, downgrade, or plan conversion would create a new deal in HubSpot, close it, trigger the notification sequence, and the finance team would pick up from there. We were manually reviewing deferred income, writing journal entries, and updating the subscription in Stripe.

Month-end close took about a week, with the deferred revenue reconciliation being the most error-prone part. Managed in Excel, it was "prone to missing things again, because it was done quite manually."

The operational cost was roughly an hour a day, every day, just to keep billing and subscription management moving, not counting month-end. And if the person responsible was unavailable, customers had to wait. "There would be a delay in setting up a customer subscription, and that obviously impacts the customer experience," Richard noted.

Matt Best, Willo^®'s Head of Customer Success, felt it too. His team couldn't easily connect the dots between new business and customer success. “There was a break point in the sequence because of the manual intervention from the finance team," Matt shared

The solution

Richard evaluated a few options. A previous tool the business had tried didn't work out. The implementation was too complex, and the scope of what was actually needed had been underestimated.

Measure was the only provider where the conversation got far enough to scope the project properly.

"Speaking to Aswin and Ruchi, it was obvious to me pretty quickly that this would be able to solve the problems I had," Richard said. "They knew exactly what I was talking about and could articulate exactly what the solution could look like."

The vision was clear: Measure would sit at the center of Willo^®'s revenue operations, connecting HubSpot, Stripe, and Xero and the Willo platform  into a single flow. From contract signature through to customer provisioning, billing, and deferred revenue recognition, all tools were connected by Measure.

The transition

The implementation required meaningful engineering work upfront. Willo^®'s product had been built on top of Stripe's subscription infrastructure, with different entitlements mapped to multiple subscriptions per customer account. Moving to Measure meant rerouting the product away from Stripe Billing and rebuilding that integration layer. The sprint was led by Willo^®'s CPO and two senior backend engineers, working closely with Ruchi and Aswin throughout.

Once the integration was complete, the engineering team stepped back entirely. Finance and customer success took over as the primary owners of Measure. No ongoing engineering tickets for billing changes. No developer involvement for new contracts or pricing updates. The work happened once, and it was done.

What stood out during the process wasn't the scope of the work; it was the support. "The level of support we received after go-live, especially from a CS perspective, was really, really nice to have," Matt said. "Having direct access to Ruchi and her team was outstanding and why I'd recommend Measure." The team also adapted as Willo^®'s own requirements shifted mid-implementation. "They were actually evolving with us and helping us achieve what we wanted to achieve as it changed."

The results

The biggest immediate win was the contract flow.

"Having our billing and subscriptions integrated with our CRM, that's the biggest time save," Richard said. “A customer can now sign a contract and get instant access to their environment, fully billed, with no manual intervention. That happens at 2pm UK time or 2am West Coast time, it doesn't matter. Nobody has to be there,” he concluded.

The single source of truth changed how the whole business operates. Sales, CS, and finance now all see the same data: who's active, who has an outstanding invoice, who's canceled. "It's not just finance that knows that. That's success, that's sales, and it’s all integrated within HubSpot as one truth."

Stripe fee savings alone are running at around £500 per month which, as Richard noted, will only grow as the business scales.

But the bigger shift is harder to put a number on. "It's completely changed the way we're able to get a customer from contract signature all the way to onboarding and activation," Richard said. "To do it as well as we're doing it now, we would have had to hire two more people full-time to do all of those steps to the standard and speed we're doing now. We're not saving a couple of hours here and there. We've really changed the way our revenue operations, billing, subscription management, and CS workflows all work."

Matt put it plainly: "You can't underestimate how much it has set us up to scale. We wouldn't be ready to scale as a business if we were still manually doing all that."

Richard ended our interview with one final thought: "I'd recommend Measure to any SaaS business with a subscription model combined with any level of manual intervention in their contracting, billing, and subscription management flow."

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