Playbooks

1. Distribution is still key when it comes to selling enterprise products at the highest levels.

SaaS startups can (and do!) land deals with big companies all the time now through the bottoms-up motion of individual teams adopting the product and paying by credit card. And they also can (and do!) expand those deals into large, enterprise-wide contracts. But the massive power of Microsoft, Salesforce, and to a lesser-degree Oracle and Google's salesforces + bundling distribution abilities enables deals to happen at a scale that most independent companies find difficult to match.

2. Enterprise products are like icebergs — 90% of the work is below the surface.

• This is true both at the tactical level (integrations, permissions, security, etc) and the strategic: providing seamless connective tissue between work apps inside and across organizations is what makes Microsoft so powerful as an enterprise player — not necessarily because their products are better.
• This is why Slack Connect was such an important initiative for Slack, and why Microsoft trained the full firepower of its Teams marketing against it, while mostly ignoring Zoom even though Zoom is much more directly competitive on the product feature front.

3. Telling your story well always matters, no matter how big you get.

Perhaps the biggest reason Slack "failed" as a public company was its inability to effectively communicate what it did that was special, why that was important, and why it was defensible enough to withstand the assault from Teams. Arguably, great answers existed to all of those questions — and the company kept posting impressive numbers to back them up — but Wall Street never bought the story Slack sold.

4. Enterprise collaboration is moving deeper into work apps themselves.

Today's native SaaS tools like Figma, Coda, Notion and others are embedding collaboration and chat natively into apps themselves — which reduces the primacy of a centralized platform like Slack, Teams or Discord. While on the one hand this is a threat to dedicated collaboration platforms, it also presents a massive opportunity: if they (or someone else) can decouple the core "collaboration layer" service from their own dedicated apps and also embed it directly into those work apps via APIs, it exponentially increases the surface area of workplace productivity that they can address.

5. The "Outsiders playbook" of growing through acquisition once your original product approaches market saturation works just as well in tech as it did in other sectors like media and industrials.

As Will Thorndike outlined in The Outsiders, many of the best CEO capital allocators of all-time utilized the grow-through-acquisition strategy very effectively. Salesforce (and other big tech companies like Facebook) are clearly adopting the same approach.

Links

• Not Boring: https://notboring.substack.com
• Packy on Twitter: https://twitter.com/packyM
• Packy's bull thesis on Slack from November 2020: https://notboring.substack.com/p/slack-the-bulls-are-typing