New Kaseya CEO Yogesh Gupta, backed by Insight Venture Partners‘ war chest, is leading a software and cloud technology buying spree that could reshape the company and the MSP industry. The first targets were Zyrion (cloud and virtualization management) and Rover Apps (BYOD security). But M&A deals also trigger plenty of cultural, business, financial and technology challenges. Can Gupta piece it all together for Kaseya and its MSP partner base?

First, the big picture: Insight Venture Partners acquired Kaseya from its founders and former CEO Gerald Blackie in July. Since that time Kaseya has acquired Zyrion (monitoring and management of virtualized and cloud workloads) and Rover Apps (BYOD security and mobile device management). Also in recent weeks, SolarWinds acquired N-able, AVG Technologies purchased Level Platforms, and ConnectWise CEO Arnie Bellini promised to be a buyer (not a seller) amid the M&A activity.

Big Deals, Opportunities and Questions

Still, the biggest moves so far this year involve Kaseya. Here are six observations, questions and opportunities facing Kaseya in the days and months ahead.

1. Right Leadership?: Yes, Gupta has extensive experience managing M&A and enterprise IT businesss. After a successful run at CA Technologies, he built FatWire and sold the company to Oracle. Gupta has a $1 billion vision for Kaseya, and he’s vowed to include MSPs in the road map while also focusing on mid-market enterprise customers.

2. Right Motivation?: Whenever a company is acquired or sold, the buyer needs to make sure the right financial perks are in place to keep employees motivated — retainers, stock, etc. I don’t know the details of each deal (Insight-Kaseya, Kaseya-Zyrion, Kaseya-Rover Apps) but I’ll be poking around to see if/how Kaseya intends to keep the best and brightest motivated.

3. Product Overlap?:

4. Right Integration?: Gupta wants Kaseya, Zyrion and Rover Apps technologies to surface in a single dashboard for MSPs. But can Kaseya’s R&D and developer teams pull together all that code? And if so how soon?

5. Right Partner Program?: Many Mobile Device Managment (MDM) companies have lousy MSP partner programs. They often lack the ability to manage end-customer billing, branding, pricing, etc. On the flip side, many MSP software companies — particularly RMM providers — have good MDM partner programs but their software has yet to really go mainstream. Can Kaseya find the right balance with Rover Apps?

6. War Chest?: Is Kaseya done buying for now? Or does Insight Venture Partners plan to make any more acquisitions?

That’s all for now. But stay tuned for more updates.