Sherweb Targets MSP Billing Gaps with HaloPSA Integration

Sherweb has launched a native integration with HaloPSA to automate cloud billing workflows for managed service providers (MSPs), delivering real-time subscription and license updates directly within the PSA platform.

The company said it is the first provider to integrate natively with HaloPSA for automated cloud billing synchronization, allowing customer license purchases and subscription changes to appear instantly in HaloPSA without manual entry.

“Conversations with HaloPSA started about a year ago as it gained popularity in the market,” Rick Stern, senior director of platform at Sherweb, told Channel Insider. 

Sherweb targets MSP billing complexity

MSPs increasingly manage a mix of recurring contracts, pay-as-you-go subscriptions, and Microsoft licensing arrangements that can change frequently throughout a billing cycle. 

PSA platforms help providers manage those workflows, but billing data delays can create reconciliation issues before invoices are sent to customers.

Sherweb said many integrations still rely on once-daily synchronization schedules, creating gaps between when a license changes and when that update appears inside the PSA platform.

The new integration with HaloPSA moves cloud purchases and billing events into the platform as they occur, according to the company.

“Getting billing right means having data that’s current, accurate, and already in the right place when you need it,” Stern said. 

“That’s often on MSPs to manage manually—syncing records, catching errors, correcting changes that didn’t track. We built this integration so that work happens automatically, and MSPs can spend that time on their clients instead.”

HaloPSA integration supports Microsoft CSP billing

Sherweb said the integration is designed to support several common MSP billing requirements, including both pre-bill and post-bill invoicing models.

The company also said the integration handles Microsoft yearly licenses billed monthly as well as bulk upfront payments — scenarios Sherweb claims are not fully supported by some other major distribution platforms.

“One of our major value propositions we bring as a CSP is that we’re a billing aggregator, and it’s crucial we can help partners get their data from one platform to use it across their stack,” Stern said.

Sherweb builds out broader automation strategy

He added that Sherweb is aware that it is far from the only piece in an MSP’s overall technology stack, from automation platforms like Pia to a variety of PSAs, RMMs, and other tooling that partners rely on to manage their clients efficiently.

The focus for Sherweb, he said, is on building repeatable, scalable internal processes to onboard integrations like this quickly moving forward.

“Ensuring we have the right level of investment internally to support this work is really important to us. We’ve added to our engineering team, and our product innovation teams around PSA integrations have grown significantly, too,” Stern added.

Expansion push continues after UK growth and funding

The HaloPSA announcement comes during a broader expansion push for Sherweb.

The company recently expanded operations into the United Kingdom, where HaloPSA is based, and earlier secured a $125 million investment from Investissement Québec to support global growth initiatives.

“We chose Sherweb because they were fast, proactive, and brought years of hands‑on expertise with a stable, experienced team,” Kevin Howell, CEO of Sherweb partner HTG, told Channel Insider in March. 

“Unlike previous distributors we worked with, where high staff turnover often caused delays and inconsistency, Sherweb’s low turnover meant we had reliable access to knowledgeable people who understood our business and could support us effectively from day one,” Howell added.

“The recent funding and the growth that will come from it are a great opportunity for us to take our message around why partners should expect better outcomes in markets we haven’t previously had much presence in,” said Stern.For MSPs, Sherweb’s recent moves reflect continued demand for tighter automation between distributors, cloud marketplaces, and PSA platforms as providers look to streamline back-office operations while managing increasingly subscription-centric customer environments.