Founder to Founder: The Guide to Building a Breakout Startup in the AI Age

Christina Cacioppo (CEO & Co-founder of Vanta) and Mario Gabriele (CEO & Founder of The Generalist) come together for a tactical deep-dive into what it truly takes to build a breakout startup. 

In a market evolving at breakneck speed, they share sharp insights and real-world strategies for staying ahead of the curve.

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The stories that inspire a startup founder to rethink their strategy differ from the tactics that help a strategy consultant nail a client project and get promoted.

The playbooks that a PM needs to embed product-led-growth loops differ from the skills a Head of Marketing needs to align their team around executing a viral campaign launch.

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Now then - onto today’s breakdown.

Slackquisitions

Chess Move

The what: A TLDR explanation of the strategy

When Slack first launched, their target users were accustomed to the sophisticated suite of features offered by incumbents like Microsoft (Skype, later Teams, and Office 365) and Google (Meet, Drive, and GChat).

To compete, Slack had to develop a comprehensive offering with feature parity as quickly as possible.

Rather than building everything themselves, Slack executed a sequence of tuck-in acquisitions of complementary products, allowing them to rapidly close their feature gap with competitors.

Between 2014-2020 Slack completed 6 acquisitions:

• 2014: Spaces - Lightweight alternative to Google Docs.

• 2015: Screenhero - Multiplayer screen sharing service.

• 2018: Hipchat & Stride from Atlassian - Slack competitors.

• 2018: Missions - Automation tool for task management.

• 2018: Astro Technology - Unified email integrations.

• 2020: Rimeto - Employee directory software.

By acquiring point-solutions with proven technologies and user bases, Slack was able to shortcut years of product development, minimise the risk of feature failures, and scale to 12 million DAUs by the end of 2020 (just 7 years after launching).

Breakdown

The how: The strategic playbook boiled down to 3x key takeaways

1.  Acquiring their way to "the operating system for work”

Slack’s biggest competitors, Microsoft and Google, had the tremendous advantage of large existing user bases from their other products.

This let them bundle in chat capabilities (Teams and G-chat) that integrate into the rest of the ecosystem.

Slack needed to create a user experience so compelling that people and companies would switch to their solution rather than use tools already accessible to them.

To compete in an already saturated market, Slack developed an acquisition strategy targeting technologies they believed to be the best in the world at their specific function.

Each of Slack’s acquisitions added best-in-class, net-new capabilities without the time investment of building them internally:

Document collaboration - (Spaces in 2014):

Collaborative screen sharing - (Screenhero in 2015):

Workflow automations - (Missions in 2018):

Email & calendar integration - (Astro in 2018):

Employee directories - (Rimeto in 2020):

These acquisitions rapidly transformed Slack from a chat tool to “the operating system for work”.

2. Eating the Competition

The 2018 acquisition of HipChat and Stride from Atlassian was Slack paying for market control.

This move wasn't just about technology, although Stride was a well built product.

It was about eliminating a competitor and migrating their users to Slack.

As part of the deal, Atlassian publicly pledged to exit the team-chat market altogether.

In exchange, Atlassian gained an equity stake in Slack and became the priority integration partner.

The 2 companies committed to “deep and powerful integrations that allow teams to collaborate”, across Jira, Confluence, Trello and more, and have since shipped > 11 joint integrations.

3. Betting on consolidation

The product strategy behind Slack’s acquisitions is to remove fragmentation through native solutions that reduce context-switching.

Rather than simply adding third-party integrations (which in some cases actually fragments user experience), Slack identified the most critical workflow junctures where users were forced to leave the platform → and then filled them.

The Astro acquisition exemplifies this approach: email remained the biggest context-switching tax on productivity, forcing users to constantly toggle between Slack and their inbox.

By acquiring and integrating Astro's technology, Slack users could handle email workflows without leaving the platform.

Through the Slack for Gmail integration:

And through the Automations builder:

Huddle meant that users don’t need to switch out to Zoom/Teams/Meet.

Spaces featured real-time group editing and commenting, as well as file sharing and search capabilities → no need to switch to Drive or Sharepoint.

Rimeto addressed the growing need for remote workers to understand who their colleagues were and what they did → no need to exit Slack to figure it out.

This focus on consolidation allowed Slack to compete with Microsoft and Google’s bundled suites while maintaining its reputation for superior user experience and flexibility.

When Salesforce acquired Slack slack in December 2020, this was founder Marc Benioff’s strategy in a sentence:

“[Slack is the] central nervous system of so many companies… We've spent more than a decade focusing on this vision for a social enterprise ... this makes it all real”.

Rabbit Hole

The where: 3x high-signal resources to learn more

We Don’t Sell Saddles Here ↗

[12 minute read]

This infamous leaked internal memo by co-founder Stewart Butterfield is a must-read for tech historians and product folk.

It concretely articulates the underlying philosophy that allowed Slack to build such a user-centric product.

Deep empathy for not just user needs, but also user emotions.

You learn something new each you re-read this one.

Why "Good Enough" Software Always Wins (According to Harvard Nerds) ↗

[32 minute read]

Teams conquered the world despite Slack being a superior product in every conceivable way.

Harvard professors theorise the uncomfortable truth about why companies choose Teams over Slack (spoiler: it’s not the features).

Why Salesforce paid more for Slack than Facebook paid for WhatsApp and Instagram combined ↗

[8 minute watch]

This deep dive explains why Salesforce paid a 30% premium to acquire Slack six months ahead of schedule.

A high-conviction move - did it work?

Click here to see one perspective.

That’s all for today’s breakdown - hope you enjoyed!

— Tom Alder and Sheldon Bishop

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→ Check it out here!

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