DeskDay
Last Updated
Overview
DeskDay gives MSPs a chat-based service desk where techs and AI agents can work on the same tickets. Its AI workforce currently centers on ticket triage and dispatch, which may limit automation for other tasks, but Helena AI Copilot can still support techs as they resolve each ticket.
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Starting Price
$79
per technician per month
DeskDay Specifications
- Analytics And Reporting
- Escalation Management
- Self-Service Portal
- SLA Management
What Is DeskDay?
DeskDay is an AI-native Professional Services Automation (PSA) platform for Managed Service Providers (MSPs) and internal IT teams. It combines a conversational service desk, workflow automation, a knowledge base, project management, billing, and reporting. End users can raise tickets by email or through IT-Connect, DeskDay’s end-user app. Its built-in AI works in three layers: Ask Helena for questions about service desk data, Helena AI Copilot inside each ticket, and AI agents that take on routine work such as ticket triage.
What Is DeskDay Best For?
A standout function of DeskDay is its conversational service desks – delivered to end users through IT-Connect. Users can raise tickets and chat with techs in real time from Microsoft Teams, a web portal, Windows or Mac desktop apps, or iOS or Android apps, and each request lands in one DeskDay queue. Context carries across channels, so a user can start on desktop and continue on mobile. These capabilities can be beneficial for technical teams and help reduce friction in IT issue reporting.
How Much Does DeskDay Cost?
DeskDay pricing starts at $79/technician/month for the Standard Plan, which includes 2 minimum seats, a knowledge base, announcements, ticketing, and contracts. Additionally, the Enterprise Plan costs $1,189/month with an annual commitment, including 10 seats, fully branded Teams, and iOS and Android mobile apps for customers. The vendor also offers a 14-day free trial which includes the full PSA platform and DeskDay AI.
Beyond the subscription, additional costs may include:
- Onboarding And Implementation: Costs $800 one-time charge for 10 hours on monthly Standard plans. It is waived on annual plans with 4+ seats. Additionally, 20 hours of onboarding support is included at no charge on the Enterprise plan
- Additional Enterprise Seats: Starts at $69/seat/month, depending on how many technicians are added beyond the included seats
- Extra Agent Actions: Costs $0.25/action, which may apply when AI agents handle more tickets than the monthly allotment covers
- DeskDay AI: $399/month and requires a DeskDay PSA Plan
Disclaimer: The pricing is subject to change.
DeskDay Integrations
DeskDay integrates with:
How Does DeskDay Work?
Here’s how teams typically set up DeskDay and move work from incoming request to invoice:
- Log in to your DeskDay account with your credentials or SSO
- Add customers and attach contracts that define how each ticket is billed
- Connect your support email and set up IT-Connect so end users can raise tickets from Teams, web, desktop, or mobile
- Review new tickets after the Triage & Dispatch Agent categorizes and routes them, and reassign any that need a different tech
- Resolve tickets in chat with suggestions from Helena AI Copilot, while timers log work time
- Approve timesheets and review billable entries in Ready-to-Bill
- Generate invoices and sync them with QuickBooks or Xero
- Build reports on customers, tickets, techs, and SLAs for QBRs
Who Is DeskDay For?
The software serves the following professionals:
- Internal IT teams
- Solo IT operators
- Growing service desk teams
DeskDay Use Cases
Based on our analysis of DeskDay’s current capabilities, the following are the scenarios where the platform can be a reasonable fit:
MSPs Billing Clients Under Different Agreement Types
An MSP may bill one client hourly, sell another a prepaid bank of hours, and charge a third per seat for Microsoft 365 and security services. Tracking all of these in spreadsheets often leads to hours running out unnoticed or seat counts drifting from what is invoiced. DeskDay can suit these MSPs because each ticket follows the contract attached to it, whether that’s hourly, prepaid, block-hour, flat-fee, or seat-based. Prepaid balances can also trigger alerts before they run out, which may give account managers time to discuss renewals before clients receive an unexpected overage.
Lean Service Desks That See Sudden Ticket Spikes
A small team can handle a normal day comfortably, but an outage or a patching issue across several clients can flood queues within minutes. When techs can only work one conversation at a time, users wait and SLA targets may slip. DeskDay’s multi-ticketing feature lets technicians pin up to seven tickets or tasks for quick access and work across multiple tickets in one interface. Multiple technicians can also be assigned to a ticket and participate in its conversation. This can help smaller service desks keep requests organized during ticket spikes.
MSPs Running Client Onboarding Projects Along With Daily Support
Bringing on a new client usually means a fixed-scope project, such as device rollouts, account setup, or a migration, running alongside that client’s regular tickets. When the project lives in separate tools, the hours spent on it can miss the invoice. DeskDay may be a practical option here because projects sit in the same system as tickets and billing, so milestone work stays tied to the client’s contract. Teams that repeat similar onboarding projects can also benefit from templates and avoid rebuilding plans each time.
Owners And Techs Who Already Work In AI Assistants
For MSP owners who draft emails, research fixes, or prepare client summaries in an AI assistant, switching back to the PSA to check a ticket or pull a report can interrupt that work. DeskDay’s MCP connector lets Claude or other MCP-compatible assistants look up tickets, update records, and reply to users from a chat. This allows owners and technicians to manage ticket-related tasks without leaving their AI assistant, reducing interruptions when handling client requests.
Is DeskDay Right For You?
If your organization wants service desk, projects, and billing to run from one chat-based system, DeskDay may be worth evaluating. It is built for solo operators as well as growing MSPs and internal IT teams, with per-technician seats that can be added as headcount grows. Most teams go live in about two weeks with guided setup. For access control, DeskDay supports SSO for techs and end users through Microsoft Entra ID, Google Workspace, Okta, or JumpCloud, built on OIDC and SAML 2.0.
Still not sure about DeskDay? Contact us at (661) 384-7070 and we can help you make an informed decision.
DeskDay Features
Helena AI Copilot
DeskDay's Helena AI Copilot suggests a root cause and step-by-step fixes on each ticket, drawn from past tickets, the knowledge base, and vendor documentation, with a confidence score on each suggestion. It drafts a reply when the ticket arrives and updates it as the conversation continues, while live sentiment and customer history sit in the same context panel. This can help L1 techs resolve issues without escalating them, though a tech must confirm every suggestion before anything is sent.
Service Desk Workflow Builder
DeskDay's workflow builder is a no-code canvas for rules triggered by conditions such as keywords, customer, VIP status, or channel. When a condition is met, a rule can auto-assign the ticket, set priority, send an auto-reply, start a timer, or close the ticket after customer inactivity. Role-based rules can also apply the correct technician billing rate. This can help reduce manual sorting for service managers.
Billing And Contracts
Billing moves time entries, products, and expenses from tickets into a Ready-to-Bill queue, where managers review and approve them before invoicing. Recurring invoices can run on schedules from daily to annually, and each can be set to auto-send or save as a draft. Finalized invoices sync with QuickBooks and Xero, which can reduce month-end spreadsheet work.
Triage & Dispatch Agent
DeskDay's Triage & Dispatch Agent asks follow-up questions on new tickets, then categorizes, prioritizes, and routes each one to a tech or queue. Teams can run it in suggest mode first, switch to auto mode later, and set a confidence threshold below which tickets go to human review. Every decision is logged with its reasoning, so managers can audit routing.
Knowledge Base
The Knowledge Base with DeskDay separates a Global KB for SOPs that apply to all clients from customer-specific folders for site procedures and network diagrams. Techs can turn a resolution note or chat into an article in one action, link articles to tickets, and co-edit with live cursors. Admins can set View, Edit, or No Access permissions per article or category, though the KB’s value still depends on techs documenting fixes consistently.
Quality Assurance
DeskDay's Quality Assurance function checks tickets, tasks, and projects against rules that managers define, and flags missing work hours, notes, ticket classification, and SLA violations on a QA Board. CSAT feedback is collected once a ticket is resolved. This can help reduce revenue lost to incomplete time entries.
Pros And Cons of DeskDay
Pros
Reduces manual ticket sorting for service managers
Speeds up recurring issue resolution
Helps protect sensitive client info with access controls
Helps prevent revenue loss from missing time entries
Reduces manual billing work and missed charges
Cons
Chat-first approach may not suit email-heavy teams
Reporting depth may feel limited for complex needs
Some workflows may still need manual oversight
DeskDay Pricing
Standard Plan | Enterprise Plan |
|---|---|
$79 per technician per month | $1,189 per month |
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Disclaimer: The pricing details were last updated on Sep 25, 2026 from the vendor's website. Please contact us for a tailored pricing list.
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Frequently Asked Questions
Can DeskDay run alongside an existing PSA or ITSM tool?
No. DeskDay designed as a complete PSA built to replace a current PSA or ITSM tool. Teams considering a switch may want to plan for moving the service desk, projects, and billing into DeskDay at the same time.
Can end users pick ticket templates in IT-Connect?
Yes, end users can pick ticket templates in IT-Connect for different issue types. This helps them submit requests in a consistent format.
Can the DeskDay Announcement feature alert end users about outages?
Yes, DeskDay's Announcement feature lets techs broadcast outage alerts, maintenance updates, and other notices to targeted end users through IT-Connect.
Does DeskDay include data migration from a previous PSA?
Yes, DeskDay includes a free data migration of historical tickets, customer records, users, and contacts from previous PSAs on every plan. Help with workflow setup and team training comes with the separate onboarding package.
Does DeskDay offer a public API for custom integrations?
Yes, DeskDay provides a public API for building custom integrations and automation, which can help MSPs connect tools that are not on the current integrations list.