DeskDay

DeskDay is a professional services automation platform from DeskDay for MSPs and IT teams, built around a chat-based service desk rather than the form-heavy ticket screens common to older PSAs. It covers ticketing across Microsoft Teams, email, web and mobile, service desk workflow automation, a knowledge base, billing and contracts, project management, timesheets and reporting, with an AI copilot called Helena working inside each ticket to draft replies, read sentiment and suggest next steps before a technician approves any action.

DeskDay suits a smaller or mid-sized MSP that wants to get a service desk running in days rather than months and is comfortable running support through Microsoft Teams and chat rather than a traditional ticket form. Pricing is published and per technician seat, not per client or per end user: the Standard plan is $59 per technician per month billed annually, or $79 per technician per month billed monthly with a two-seat minimum (checked September 2026). An Enterprise plan adds full white-label branding across the Teams, mobile and desktop apps for $499 a month, which includes five technician seats with additional seats at $69 a month. Every plan starts with a 14-day free trial and there is no free version. A one-time $800 onboarding fee applies to the Standard plan unless billed annually, in which case it is waived.

DeskDay integrates with the RMM platforms NinjaOne, Datto RMM, N-able N-central and Level, the documentation tool Hudu, and the accounting platforms QuickBooks Online and Xero. The vendor also lists integrations with ConnectWise Automate, N-able N-sight, Syncro, SuperOps, ITGlue, Pax8, Acronis, Veeam and several remote-access and payment tools as coming soon rather than live. DeskDay is built by its parent company WorkSent (formerly Eynetech), which has worked as a white-label MSP support provider for over a decade; DeskDay itself reached general availability in 2024. MSPs should confirm that any tool outside the current active integration list is not one they depend on day to day, and should check on a trial whether Helena's AI suggestions and the chat-first workflow fit how their technicians actually work, since this is a newer product without the years of field use that older PSAs have.

DeskDay is worth a look for a smaller MSP that finds ConnectWise PSA or Autotask too heavy to configure and is willing to run support through Microsoft Teams and chat rather than a classic ticket form. Its per-technician pricing is published and notably lower than HaloPSA's, and there is no per-end-user charge. The catch is maturity: several integrations MSPs rely on, including ConnectWise Automate and ITGlue, are still listed as coming soon rather than live, and the company itself is only a few years old. Use the 14-day trial to check that your specific RMM, documentation and accounting stack is on the active integration list today, not the roadmap, before committing.