Autotask Community Live is set to host hundreds of managed services providers (MSPs) starting June 2 in Phoenix, Ariz. For Autotask and the broader MSP market, the conference represents a timely inflection point. Here are 20 questions MSPmentor will explore as we catch up with CEO Mark Cattini, Senior VP Len DiCostanzo and other company leaders.

First, a little background: It has been 2.5 years since Cattini joined Autotask and outlined a global initiative — localizing the company’s SaaS-based business management platform for MSPs across the globe. The company now has more than 50 employees in England, and more than 50 percent of new sales come from outside North America. 

But where does Autotask go from here? Among the questions we’ll pose to various executives…

For CEO Mark Cattini and CFO Vince Zumbo…

1. Executive Scorecard?: Cattini is 2.5 years into his journey as CEO. And Zumbo has been a key advisor as CFO — lining up funding for the global expansion. How would you each grade your performance and Autotask’s performance during that journey?

2. SaaS Valuations?: During the Autotask Community Live 2012 conference, Cattini positioned Autotask as a SaaS company and mentioned the valuations of well-known SaaS businesses — some public, some acquired. Can Autotask, working within the MSP market, build the type of momentum seen at NetSuite (N) and Salesforce.com (CRM)?

3. Venture Capital, Private Equity … and an Exit?: Autotask raised $6 million in December 2011 to fund international expansion. Are existing Autotask investors remaining on-board for the long haul? Might the company raise more money? Or is an exit now a near-term possibility? (Note to readers: This is pure speculation on my part. I have not heard any rumors about a near-term exit…)

3a. Bonus — Any reaction to SolarWinds (SWI) Buying N-able for $120 million or 5 times annual revenues?

4. SaaS Platform Expansion?: Could Autotask be extended to become a potential ISV platform, the way Salesforce.com offers Force.com? If so, what potential gaps could ISVs fill in the MSP market?

5. Vertical Market Expansion?: Right now Autotask focuses purely on IT services providers. But what about other services-driven industries — might Autotask ever consider a move into those markets?

For Senior VP Len DiCostanzo & VP of Marketing Scott Opiela…

6. Personal Evolution?: DiCostanzo joined Autotask in 2008 after running his own IT services organization. He witnessed, first-hand, Autotask’s transition from founder Bob Godgart to current CEO Mark Cattini. How has DiCostanzo’s own approach to Autotask’s community evolved over the past few years?

7. MSP Evolution?: DiCostanzo has educated IT service providers about the transition to monthly recurring revenue (MRR), pricing strategies and service management. How has his approach to education changed in the past year, and how must it continue to evolve as MSPs explore cloud services, mobility and other disruptive technologies? Same question to Opiela on the marketing-to-MSPs front.

8. Emerging Services?: What new IT services — which perhaps didn’t exist in 2008 or so — are MSPs introducing now? How is Autotask marketing those trends to MSPs?

9. Fading Services?: Which classic managed services are going away or suffering from profit margin fall-off?

10. Localization Evolution?: As DiCostanzo travels between the US, Europe, Asia and more, how would he compare and contrast the relative maturity of each MSP market and the trends in each market?

For Senior VP Global Sales Kevin Donovan and VP of Client Services Tom Osborn…

11. Channel Strategy Evolution?: On the one hand Autotask sells to MSPs globally. But on the other hand I believe Autotask has relationships with distributors that engage MSPs in specific regions. How might the sales strategy evolve as Autotask seeks to accelerate its globalization and localization strategy?

12. Regional Momentum?: It sounds like the UK is now Autotask’s most successful region outside of the United States. How much more momentum can you gain in the UK, and what other regions are demanding your immediate attention?

13. Average MSP Size, Sale?: I believe Autotask has de-emphasized its starter product (Autotask Go) in recent years and has been seeking to attract larger MSPs onto its platform over the past two years. Can you offer any clues about Autotask’s average deal size and whether it has been growing?

14. MSP Retention?: MSPs sometimes jump from one software platform to another. How is Autotask performing in terms of MSP retention?

15. MSP Onboarding?: Let’s assume I’m an MSP that signs up for Autotask. Has the onboarding process evolved in the past few years? How quickly can an MSP begin to leverage Autotask-developed best practices as it seek to automate business tasks?

For VP Engineering Adam Stewart & VP Product Management Patrick Burns…

16. Life After VARstreet?: Autotask sold the VARstreet business in December 2011. Sure, this is old news. Generally speaking MSPs didn’t suffer from the Autotask-VARstreet divorce. But far more importantly, how did the VARstreet sale allow Autotask to re-focus its efforts on the core SaaS platform?

17. Open APIs?: Cattini talks about them all the time. But can you describe what types of new ISVs have integrated with Autotask? How has the lineup of integrated third-party options evolved in the past three years?

18. Core Components?: The Autotask SaaS platform includes CRM, service desk, contracts, billing, reporting and more for MSPs. Which modules require the most enhancement — and what new modules might be on the way?

19. Mobility?: Just how mobile is Autotask’s platform these days? And what new mobile- and browser-based capabilities might we see in the months to come?

20. Gamification of Autotask?: Some MSP-centric software companies, such as Quosal, are thinking and talking a lot about the gamification of IT. Are game-type enhancements coming to Autotask or is this a passing fad?

Bonus Coverage…

In addition to catching up with Autotask’s executive team, MSPmentor will be on hand to meet with a range of MSP-centric technology companies at the conference.