How challenging is it to sell against competitors in the sales department at Slack?

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I worked specifically selling to Large Enterprise.  Selling against Microsoft was very challenging.  If a company already is Wall to Wall Teams, it's more of a slog to get a deal done.  This is for two main reasons IMHO -- perception of Teams as "free" as its cost is already bundled with Office and the inertia / blocking by Enterprise IT because of their commitment to Microsoft.   I believe Slack would be more competitive if Salesforce sunset both Chatter and Quip.

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On addition to the previous response I will add that Core AEs won't help because - from their perspective - pushing Slack against Microsoft will create friction with their CIO sponsor and they don't want to harm their existing relationship on core products... A shame...

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Incredibly tough - whilst there was hope that the Salesforce acquisition would lead to a slick co-sell motion with the Salesforce sales org; in reality that's not happened at all.

Whilst Slack is a very powerful tool when used well, the majority of the market just view it as a chat tool. And an expensive one at that. So until the market matures and begins to understand the concept of Slack being a place where work gets done (leverage automation, integrate with other key systems, create a hub that captures both system events and human events etc...) I think Slack will continue to struggle.

Majority of closed won deals recently are just upsell to existing accounts - selling to net new customers is savage. I've worked in sales for close to 15 years and Slack is by far the hardest product I've had to sell.

Salesforce / Slack also don't make it easy for AEs either - it's a seed-and-grow product (e.g. sell a few licenses to one small team in a business but in time it can spread across lots of functions / teams) and yet they set minimum deal size thresholds (which are actually quite high) that need to be hit in order for the AE to be recognised on a deal. This, along with how they bundle with other Salesforce products, need to change in order to drive a more successful sales motion.

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Competing against Microsoft and the perception that Teams is “free” since it’s bundled into O365 was incredibly challenging. The value prop Slack now has thanks to the SF acquisition is Slack’s integration with SF products (ie slack + sales cloud, slack + service cloud, etc). This can go a long way.

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I agree with the other responders. I'm also in Large Enterprise and you're often viewed as a necessary evil. The sale is less about the value and more about InfoSec/Legal compliance and that's not fun. Salesforce will eventually get the integration piece right but as of 2023 it's smoke and mirrors. If they can actually create an invaluably integrated piece of the Salesforce ecosystem then it will be easier but still a challenge. Most sales are harvesting users from existing accounts and/or getting them to upgrade. Great product but the time to sell Slack was 4-5 years ago.

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Short answer is : almost impossible if CIO has his hands tied to Microsoft. ie. 90% of the time. Maybe easier in the US, but in Europe, you can only penetrate some departments within large accounts.
Teams is not free and there are many reports re. hidden costs (+ timing + complexity + bad user sentiment...) of Teams deployment. But no CIO wants to hear this story : it's bundled with O365 and the capabilities are not mission critical... Add to this situation the fact that Salesforce is not leveraging Slack. 2.5 years after the acquisition, you still find Quip and Chatter. Could be an easy shift for all Salesforce customers, but my guess is that Slack is not a strategic product at Salesforce. Maybe itt has never been. Zero effort on co-sell between core products and Slack in order to penetrate large accounts.

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How challenging is it to sell against competitors in the sales department at Slack?