Day two of Kaseya DattoCon 2025 was all about momentum — embracing change, innovating boldly and celebrating the people who make the MSP community exceptional. From market-defining insights and actionable growth strategies to a show-stopping keynote with Mindy Kaling, the day reinforced one message: the MSP industry’s future belongs to those who lead with adaptability, efficiency and heart.
Riding the wave of change: The new MSP market opportunity
The day opened with a look at the massive transformation reshaping the MSP landscape. Speakers emphasized that AI and evolving business models are rewriting how MSPs deliver value, creating both new opportunities and new risks.
Venture-backed “AI-first” MSPs are already experimenting with innovative service lines and usage-based pricing, signaling that a new era is underway. Those who start adapting now by shifting away from per-seat pricing and embracing hybrid models will be the ones setting the standard, not scrambling to catch up.
As technology advances, the true role of an MSP has become even clearer — to serve as a trusted advisor helping clients navigate complexity in AI, cybersecurity, cloud and SaaS. It’s shifted from managing technology to helping customers grow their business with confidence.
Shifting mindsets to stay ahead
Gary Pica, Kaseya’s Chief Community Officer, opens day two of Kaseya DattoCon
Gary Pica, Kaseya’s chief Community Officer, urged MSPs to take a step back and ask a fundamental question: What business are we really in?
Much like the ice trade’s collapse after the invention of refrigeration, the danger lies in focusing on products rather than purpose. MSPs don’t just sell technology — they sell outcomes like reduced risk, improved performance and stronger profitability.
By defining their business around customer success rather than service catalogs, MSPs can stay agile, embrace new platform shifts like AI and compete effectively in a rapidly evolving market.
Driving growth through efficiency and AI
Efficiency was presented as the engine that powers every successful MSP, and the foundation for scaling intelligently in an AI-driven world.
Attendees were encouraged to benchmark operational efficiency through metrics like seats supported per technician, ticket resolution time and ticket volume per user. However, efficiency doesn’t stop at the help desk — it extends across every department. From marketing and finance to HR and service delivery, every process contributes to how well an MSP can innovate, compete and grow. By embedding AI into everyday operations, MSPs can streamline repetitive work, enhance productivity and unlock new service offerings that address clients’ most pressing challenges.
Building stronger client relationships through strategic engagement
As technology evolves, so must the MSP-customer relationship. The most successful providers today are redefining the VCIO role to go beyond technology management and into true strategic partnership.
Attendees were urged to evaluate who they engage with inside customer organizations and how those relationships impact business outcomes. Understanding clients’ cloud application usage, operational priorities and growth goals can reveal entirely new opportunities for support.
The takeaway to attendees was to lead with insight, not invoices. Asking better questions, aligning to business objectives and delivering measurable outcomes builds trust and keeps customers coming back year after year.
Celebrating the MSP community
Dan Tomaszewski, EVP of channel at Kaseya, presents the highly anticipated Golden Datto Awards
The afternoon brought one of DattoCon’s most anticipated moments: the Golden Datto Awards, hosted by Dan Tomaszewski, EVP of channel at Kaseya. The ceremony recognized the resilience and innovation that define the MSP community.
With over 1,000 nominations submitted, the excitement in the room was palpable as four standout winners were announced:
- MSP Innovator Award: John Guillaume, Dynamic Quest
- MSP Rising Star Award: Christopher Sachse, Network Coverage LLC
- MSP Community Leader Award: Craig Bachelor, Bachelor Technologies
- 2025 MSP of the Year: Sean Fullerton, NSN Management
Tomaszewski praised the community’s commitment to showing up for one another, especially during crises like ransomware attacks and service outages. “Our industry’s strength comes from grit, generosity and showing up when it matters most,” he said. The awards were a reminder that behind every successful MSP is a team driven by purpose and a deep sense of service.
Lessons in leadership and creativity with Mindy Kaling
Comedian, writer and producer, Mindy Kaling, speaks to a packed house of Kaseya DattoCon attendees
One of the day’s biggest highlights came from Mindy Kaling, who brought her signature mix of humor, honesty and inspiration to the stage. She reflected on joining “The Office” at just 24 as the only woman — and person of color — on the original writing staff, a role that taught her how to thrive in competitive environments and trust her instincts. She shared behind-the-scenes stories from fan-favorite episodes like “The Injury” and the iconic Jim-and-Pam wedding — moments that taught her the value of persistence and creative confidence.
As showrunner of “The Mindy Project,” Kaling discovered that true leadership means empowering others, not simply being in charge. She spoke about creating inclusive writers’ rooms and how collaboration leads to stronger results, a message that resonated deeply with the MSP community. Like leading a diverse IT team, great storytelling — and great service delivery — depend on empathy, trust and listening to every voice at the table.
Kaling also shared what drives her today: the fear of failure and the responsibility of providing for her three kids. That candid admission struck a chord with attendees who know the weight of constant delivery and client expectations. As she reflected on her journey, Kaling encouraged attendees to move forward even when things feel uncertain. Confidence and persistence are what turn ambition into success.
Looking ahead
Kaseya DattoCon closes with a Carnaval Calle Ocho–themed celebration
As day two came to an end, one message stood out: the MSP industry is entering a defining era of change and opportunity. Those who embrace new ways of working — driving efficiency, innovation and strategic value — will be the ones shaping what comes next.
The conference closed with a Carnaval Calle Ocho–themed celebration, filling the evening with vibrant colors, music and well-earned excitement. It was a fitting finale to a week that celebrated progress, community and the unstoppable spirit of MSPs everywhere.
