Bold and far-reaching is one way to describe the recent move by software company Salesforce.com (Salesforce.com Stock Quote, Chart, News, Analysts, Financials NYSE:CRM) to acquire Slack for $27.7 billion, and while the strategy might win out in the end, Salesforce.com won\u2019t have an easy time toppling the likes of Microsoft (Microsoft Stock Quote, Chart, News, Analysts, Financials NASDAQ:MSFT). So says portfolio manager Paul Harris of Harris Douglas Asset Management. \u201cOne of the things with Salesforce is that it has acquired a lot of businesses, with Slack being their biggest purchase,\u201d said Harris, partner at Harris Douglas, who spoke on BNN Bloomberg on Thursday. \u201cAnd so I think it all comes down to how does Salesforce integrate Slack into their other businesses, and I think some of Salesforce\u2019s acquisitions in the past have not been integrated that well.\u201d Salesforce dropped the news on December 1 that it had a definitive agreement to acquire messaging platform Slack for about $26.8 billion in cash and 0.0776 Salesforce shares for every Slack share. Already a customer relationship management (CRM) giant, Salesforce said combining forces with Slack was \u201ca match made in heaven,\u201d according to CEO Marc Benioff, who said the merger would bring about \u201cthe future of enterprise software\u201d and \u201ctransform the way everyone works.\u201d The initial response by the market was none too bright, however, although investor reaction on December 1 was also mixed with impressions of the company\u2019s simultaneously-released third quarter results, which forecasted slower-than-expected growth up ahead. Salesforce\u2019s share price did exceedingly well for almost all of the 2010-2020 period, including last year where the stock returned 37 per cent. But CRM stalled over the last few months of 2020 and then hit a pretty significant pullback with the twin December 1 releases. Since then the stock has been flat. But Salesforce is nothing if not ambitious. Benioff has been clear about his plans to double the company\u2019s revenue from the $25.5-billion projected for its fiscal 2022. \u201cI have a $50 billion (revenue) dream, which is what I\u2019m shooting for,\u201d Benioff said on CNBC\u2019s Mad Money on December 1. \u201cI feel very excited and motivated on everything that we need to do to double the company once again, and to make that happen we have to architect a complete solution.\u201d Salesforce reported fiscal third quarter 2021 revenue of $5.42 billion, up 20 per cent year-over-year, and EPS of $1.15 per share compared to a loss of $0.12 per share a year earlier. Analysts were calling for $5.25 billion in revenue and earnings of $0.75 per share. Looking ahead, management guided for fiscal fourth quarter earnings of $0.73-$0.74 on revenue between $5.665 and $5.675 billion. (All figures in US dollars.) Harris said Salesforce, which recently joined the 30 companies that make up the Dow Jones Industrial Average, will need to get even bigger if it\u2019s looking to take on Microsoft. \u201cThe issue with Salesforce is, is the idea to compete with Microsoft (which is what some people think) and the other thing is how do they integrate that into a lot of what they presently do?\u201d Harris said. \u201cIf it is to compete with Microsoft then they are probably going to have to make more acquisitions to compete on things like Microsoft Teams and its Office products,\u201d Harris said. \u201cBut acquisitions are always scary things because they\u2019re all about execution. And is now their biggest acquisition, so I think that\u2019s really the key story over the next several quarters and maybe even the next several years: how they integrate it and actually grow their business.\u201d Slack also delivered quarterly earnings on December 1, where its third quarter fiscal 2021 featured revenue up 39 per cent year-over-year to $234.5 million and positive earnings of $0.01 per share. Both top and bottom lines beat analysts\u2019 estimates. Slack, which went public in a much-anticipated IPO in early 2019, is seeing strong uptake of its platform while the company registered 12,000 net paid customer additions, up 140 per cent year-over-year. At the same time, it\u2019s unclear whether Slack will be come the widespread work communication model of choice going forward, something Salesforce is betting on. \u201cRemember, Slack was given away for free, basically, and then you have to pay for an upgraded thing if you want,\u201d said Harris, \u201cso, how Salesforce brings the rest of their clients onto Slack and whether or not they\u2019ll pay, those are the big questions. I don\u2019t think you\u2019re see answers for the next little while, so the stock may be volatile because of that.\u201d \u201cIt\u2019s hard to judge growth companies. The best way to look at these things is do their businesses have a moat? Are they almost not monopolies but oligopolistic in their nature that they can actually control their business?\u201d Harris said. \u201cSalesforce has been able to grow their business very aggressively over the last several years I think one of the things that analysts have found very difficult about the story is that they constantly beat their numbers but it\u2019s been hard for analysts to gauge their what the company is going to do, whether they\u2019re going to get to $50 billion or not,\u201d Harris said.