Dec 7, 2020 · 28m · another-podcast
Slack, Salesforce and the future of work
0:00 / 0:00
gold bands on the timeline = statements, start to end. Hover to read, click to jump. CC turns on captions
Tony Cameron Brown and Bernadette Kevins analyze Salesforce's multi-billion-dollar acquisition of Slack, examining the structural shift from email to enterprise substrates, the realities of enterprise software sales, and the recurring industry cycles of bundling and unbundling.
How this conversation actually went
Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. How this is scored →
The hosts as informed peer 8.5 Guest teaching 1.6 Guest disagreement 1.0 The hosts pushing back 1.4
speaking balance: gold is the hosts, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 6:58 Challenging the scalability of collaborative point tools
Bernadette contrarianly questions the broad enterprise viability of Silicon Valley darlings like Notion, Airtable, and Slack outside small tech-forward teams.
Hardest push from the hosts ▶ 9:35 Deconstructing consumerization of IT idealismBernadette pushes back firmly against the romantic Silicon Valley belief that superior UX guarantees organic adoption in regulated, bureaucratic enterprises.
Biggest teaching moment ▶ 13:40 Exposing the sales spending reality of SaaS giantsBernadette cites Salesforce's financial filings, highlighting that 7 billion of 15.5 billion dollars went directly into sales and marketing to maintain retention.
The host holds their own ▶ 27:07 The cyclical replacement of Oracle by SalesforceBernadette demonstrates deep industry knowledge by outlining how Salesforce has accumulated complexity and consultancy ecosystems, turning into the new Oracle.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | The hosts as informed peer | Guest teaching | Guest disagreement | The hosts pushing back | Why |
|---|---|---|---|---|---|---|
| The Thesis of Slack as Enterprise Substrate | 8 | 2 | 1 | 2 | Bernadette Kevins sets out the fundamental thesis of Slack as a universal enterprise substrate and historical central point of truth. Tony Cameron Brown agrees completely, validating the concept with real-world onboarding examples from NationBuilder. | |
| Convergence of Messaging, Documents, and Collaboration Etiquette | 8 | 1 | 1 | 1 | The conversation explores how software expands to encompass both messaging and document layers, referencing tools like Quip. Tony adds practical observations on communication etiquette breakdown, while Bernadette illustrates cross-tool fragmentation. | |
| Communication Overload and Dedicated Tool Scaling | 8 | 2 | 1 | 2 | Bernadette critiques how general collaboration apps like Airtable and Notion suit small teams but struggle as companies scale to specialized tools. Tony backs this up with statistics on how only a tiny fraction of enterprise users actually leverage deep integrations. | |
| Enterprise Software Route to Market Realities | 9 | 1 | 1 | 2 | Bernadette punctures the Silicon Valley myth of bottom-up enterprise adoption, explaining the complex realities of procurement, IT integration, and sales engineering. Tony reinforces this with his frontline campaign software sales experiences. | |
| Salesforce's Sales Engine and Customer Success Model | 8 | 2 | 1 | 1 | Bernadette breaks down Salesforce's financials, showing how roughly half of their revenue is reinvested directly into sales and marketing. Tony concurs, discussing customer success and retention economics learned from enterprise veterans. | |
| Microsoft Teams and the Power of the Office Bundle | 9 | 2 | 1 | 1 | Bernadette details how Microsoft leverages the Office bundle to distribute Teams across corporate environments outside Silicon Valley. He also recounts the founding lore and valuation trajectory of Stewart Butterfield's companies, with Tony reacting in agreement. | |
| From Lotus Notes to SaaS Bundling Cycles | 9 | 1 | 1 | 1 | Bernadette walks through historical computing cycles from Lotus Notes to contemporary SaaS unbundling, drawing analogies to Facebook and Craigslist. Tony affirms how these architectural cycles recur throughout tech history. | |
| The Trade-off Between All-in-One Suites and Point Solutions | 9 | 2 | 1 | 1 | The speakers discuss the perennial tension between integrated suites and specialized point solutions like Shopify. Bernadette concludes with a sharp thesis that tech giants inevitably become the legacy incumbents they originally sought to disrupt. |
Statements from this episode (17)
Kevins: Slack functions as an enterprise substrate linking to underlying tools
“So the theory would be, no, it'll be in Slack. And Slack will then link you out to the Evernote or the Salesforce or the Jira or whatever the underlying tool that's the storing that is. So it's like your universal substrate for sharing and communicating and fi…”
Kevins: Central communication layers risk commoditizing underlying apps like Salesforce
“One of them is there's like a, an ownership layer that if everything happens in Slack or indeed happens in teams, which is Microsoft's attempt to do the same thing. Then that becomes more important than the apps that you're using, and so it makes it easier, th…”
Kevins: Messaging tools expand into documents while document apps add messaging
“All messaging tries to add documents, and all documents try to add messaging.”
Kevins: Workplace Communication Overload Is an Organizational Issue, Not a Software Problem
“Problem, I have too much email. Solution, we'll move to Slack. Problem, I have too much Slack. I have too many Slacks. I will, like, that's not a software problem, that's something else.”
Kevins: Growing Companies Outgrow General Tools Like Notion for Dedicated Enterprise Software
“And so I wouldn't, you know, all the usual names, Airtable, Notion, Slack, all of these things, they all sort of presume there's about 15 people, and they're all doing lots of different things, and they all need to share everything that they're doing with each…”
Brown: Only 5% to 10% of Users Utilize Slack's Full Feature Breadth
“It's basically, there's numbers probably wrong, but it's like five or 10% of people who actually use the breadth of the software. And we're not expecting everyone to use a hundred percent of the software that's been created, but very few people actually do all…”
Kevins: Edtech and Healthtech Software Are Terrible Due to Disconnected Buyers
“And what you discover is that education software is bought every seven years by people who've never been in a classroom. And so that's why it's terrible. And the same with healthcare software, that you have all these layers of purchasing process and incentive.”
Kevins: 95% of enterprise users require direct sales and IT support
“No, five percent of people will see it, realize it, and adopt it, and be able to get the company to buy it. The other 95% of people, you need to tell them it exists, you need to tell them why, and then you need to help them work out how on earth they're going …”
Kevins: Salesforce spent $7B on sales and marketing for $15.5B revenue
“They had 15 and a half billion dollars of revenue, and they spent seven billion dollars on marketing and sales.”
Kevins: Outside Silicon Valley, everyone uses Microsoft Office
“Outside Silicon Valley, everybody uses Office, and actually a lot of people use those features, or everyone uses some of those features.”
Kevins: Lotus Notes was an early, pre-internet predecessor to Slack's platform vision
“Lotus Notes was a vision of Slack, or a different version of that. It was a vision, the vision of Lotus Notes, and I'm not going to get this exactly right, but basically the vision of Lotus Notes was that it was a programmable environment. So it's this applica…”
Kevins: Every template in Excel's 'File New' menu becomes a standalone company
“So you used to say that if you do file new in Excel, and you get all those different suggestions for different templates, each of those becomes a company.”
Kevins: Shopify succeeded by unbundling complex workflows from WordPress
“Shopify is a hundred billion dollar WordPress plugin. And just to be really clear, I'm not saying literally, like, a hundred, you know, Shopify does what you ought to be able to do with a plugin to WordPress, except it's too difficult, and it's too verticalize…”
Kevins: Startups will unbundle Shopify by simplifying niche vertical workflows
“And then 10 people will do that to Shopify. Like, theoretically, I could sell a subscription newsletter in Shopify, except no, it's a lot easier to do it the way that I, in Substack or Memberful, depending on what you wanted to do. And I'm, there's a lot of pe…”