Autotask Community Live 2025 recap: 20 years of progress

Autotask Community Live (ACL) 2025 marked a major milestone: 20 years of Autotask innovation. Hosted at the historic Eden Roc hotel in Miami Beach as part of the Kaseya DattoCon 2025 pre-day, this year’s ACL reached maximum capacity, highlighting the Autotask community’s ongoing commitment to innovation and shared success.

In his keynote, Kevin Sequeira, general manager of Kaseya’s PSA Suite, explored the future of IT operations in the AI era. He shared Kaseya’s vision for agentic AI, describing it as intelligent systems that not only assist but take meaningful action. He also explained how IT leaders can prepare their teams and processes for this shift. The day’s sessions built on that message by focusing on the foundations of IT operations — documentation, workflows, contracts and financial systems — to help MSPs position themselves for long-term success in an AI-driven future.

From platform evolution and AI breakthroughs to service excellence and business transformation, ACL 2025 focused on what’s driving results now — and what’s next.

Simplifying contract management with Umbrella Contracts

A major highlight at ACL was Umbrella Contracts in Autotask, launched in the 2025.5 release with rollout beginning October 16. Umbrella Contracts reimagine how MSPs handle complex billing. MSPs spend about 22 hours a month managing scattered service contracts — time that can be reclaimed through a unified, flexible structure.

The new interface features inline editing and sleek side drawers instead of pop-ups. Each line item can have independent start and end dates, and teams can set future rate changes in advance while keeping historical records intact.

Service packages have evolved as well — each child item supports independent quantity and cost tracking, while billing remains simple at the parent level. The roadmap includes automated renewals, API support and data warehouse integration for deeper insights.

AI-powered operational excellence

Kevin Sequeira, general manager of Kaseya’s PSA Suite, celebrates 20 years of Autotask

AI adoption across Kaseya’s IT operations suite has accelerated quickly. To date, Cooper Copilot has generated more than 640,000 technician notes, 260,000 ticket summaries and 58,000 resolution write-ups, totaling almost a million AI-assisted actions that save technicians time and improve service quality.

Cooper Copilot in Autotask now powers Smart Ticket Summaries, Smart Resolution Summary, Smart Writing Assistant and Smart Ticket Triage to help technicians work faster and communicate more clearly. Frank Marino, COO of Forthright Technology Partners, said these capabilities have reshaped his team’s efficiency and compared the impact to “gaining another technician who never sleeps.”

In documentation, IT Glue’s Smart SOP Generator and Smart Relate simplify knowledge capture by automatically recording browser sessions — clicks, keystrokes and inputs — and turning them into ready-to-use procedures. Upcoming enhancements include blur tools, resizable hotspots and desktop recording, which is planned for February 2026.

AI is also driving smarter reporting and customer success workflows. Upcoming QBR enhancements will use AI to suggest review topics, highlight risk areas and help MSPs showcase measurable value to clients with less manual preparation.

Kevin Sequeira described the next stage as agentic AI: systems that not only generate text but also take action. He emphasized that AI’s role isn’t to replace technicians, but to help them work smarter and focus on higher-value tasks.

Smarter financials from quote to cash

Billing, payments and procurement were a major focus at ACL, with the introduction of new tools and integrations designed to simplify financial operations for MSPs. Together, the Smart Accounting Hub and the quote-to-cash trifecta (which brings together Kaseya Quote Manager, Autotask and ConnectBooster) create one connected revenue process from proposal to payment.

Key updates include:

• Smart Accounting Hub now syncs with QuickBooks Online every 15 minutes, giving teams near real-time financial accuracy. It also includes error logging for easier troubleshooting, multi-admin permissions (rolling out soon) and inventory reconciliation, which is planned for year-end.
• Amazon Business integration allows users to search for and order products directly within Kaseya Quote Manager, reducing manual data entry and speeding up procurement.
• ConnectBooster “Pay Now” adds a seamless way for clients to pay invoices through the Autotask Customer Portal, improving collection times and cash flow.
• PEPPOL-compliant e-invoicing launches in Belgium and will expand to additional European regions through 2026, helping MSPs stay compliant with local regulations.

Together with ongoing usability updates like unified workforce planning and an all-new Outlook extension, these enhancements streamline how MSPs manage operations, from scheduling and service delivery to billing and payment.

Operational excellence in action: The MSP panel

Panelists Erick Simpson, Roman Shain, Koby Dudley, Dan Meraz, and Rich Freeman share real-world insights on achieving MSP operational excellence at Autotask Community Live 2025.

Moderated by Erick Simpson and Rich Freeman of Channel Mastered, the MSP Operational Excellence panel featured Roman Shain (NERO Consulting), Koby Dudley (BECA) and Dan Meraz (Fairway IT Solutions), three leaders transforming operations through Autotask, IT Glue and AI automation. They shared the following insights:

• Koby Dudley shared a milestone every MSP leader dreams of: taking a vacation without needing to check in. Automation and process maturity now sustain his team’s performance independently.
• Roman Shain described how integrating PSA, documentation and monitoring eliminated silos and improved SLA visibility.
• Dan Meraz highlighted a collaborative leadership style — a “Captain Picard, not Captain Kirk” approach — prioritizing input and shared ownership.

Together, they championed an 80/20 model: automation handles the repetitive work, while humans focus on problem-solving, creativity and customer care.

Looking ahead

Autotask Community Live 2025 closed on a note of gratitude and optimism. The event celebrated two decades of innovation, collaboration and customer success while looking ahead to an even more connected and intelligent future.

With faster release cycles, smarter automation and a roadmap shaped by the community, Autotask continues to build on its legacy as the platform powering MSP growth. Stay tuned for more DattoCon updates and highlights in the days ahead!