Jul 13, 2023 · 1h 16m · in-depth
Lessons from Slack on decision making, product-led growth, and taking big swings | Noah Desai Weiss
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gold bands on the timeline = statements, start to end. Hover to read, click to jump. CC turns on captions
Noah Desai Weiss, Chief Product Officer at Slack, shares tactical insights on balancing data with product intuition, accelerating decision velocity, scaling from product-led growth to enterprise distribution, and fostering high-conviction product teams.
How this conversation actually went
Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. Brett holds 14.5% of the talking time here. How this is scored →
Brett as informed peer 3.9 Guest teaching 4.5 Guest disagreement 1.2 Brett pushing back 1.3
speaking balance: gold is Brett, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 2:50 Pushing back against data-driven dogma
Weiss directly rejects the dominant industry fashion that product decisions must be justified through continuous AB experiments, arguing empirical metrics fail on non-incremental bets.
Hardest push from Brett ▶ 23:32 Berson questions the viability of consumerized B2B softwareBerson challenges Weiss's core thesis by pointing out that virtually no companies reaching over one billion dollars in recurring revenue rely solely on end-user delight over top-down enterprise sales.
Biggest teaching moment ▶ 56:50 The evolution from anti-sales PLG to carrier-grade enterpriseWeiss candidly breaks down the operational fallacies Slack endured, recounting how founder dogma against enterprise sales required multi-year cultural corrections.
Brett holds their own ▶ 40:45 Berson's decision quality vs outcome frameworkBerson brings strong intellectual leadership to the interview by offering a clear heuristic on evaluating decision quality independently of luck and outcomes.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Brett as informed peer | Guest teaching | Guest disagreement | Brett pushing back | Why |
|---|---|---|---|---|---|---|
| Challenging Data-Driven Dogma with Product Intuition | 3 | 5 | 2 | 1 | Weiss challenges standard Silicon Valley dogma that product teams must be strictly data-driven, arguing data only solves easy problems. Berson asks clarifying questions about how this impacts the product workflow without pushing back. | |
| Balancing Data, Taste, and the Day One Project | 4 | 5 | 1 | 1 | Weiss explains how reaching a local plateau on onboarding led to the Day One initiative, and argues product taste can be developed through repetition. Berson acts as an engaged facilitator drawing out tactical examples. | |
| Scaling Product Judgment Through Principles and Strategy | 4 | 4 | 1 | 1 | Berson sets up the difficulty of scaling subjective taste across a product org compared to metrics. Weiss details Slack's product principles developed to scale founder judgment. | |
| Navigating Horizontal Adjacencies and PM Superpowers | 4 | 5 | 1 | 1 | Weiss discusses evaluating horizontal adjacencies and matching PM strengths to specific domains like self-service versus enterprise. Berson poses thoughtful questions about org design. | |
| Underrated Qualities: Writing, Decision Velocity, and Team Vibe | 3 | 4 | 1 | 1 | Weiss highlights concise writing, decision velocity, and team vibe as crucial underrated traits in remote setups. Berson playfully jokes about the Gen Z terminology. | |
| Customer Obsession and Consumer-Grade Enterprise Software | 5 | 5 | 2 | 4 | Berson pushes Weiss on Slack's consumer-grade enterprise model, noting almost no other scale B2B software companies with over a billion in revenue operate this way. Weiss defends the model while acknowledging its limits in top-down buyer categories. | |
| Cross-Pollinating Product and Go-To-Market with Salesforce | 4 | 4 | 1 | 1 | Weiss explains how Salesforce prototypes narrative and positioning leading up to Dreamforce, mirroring how Slack prototypes software. Berson inquires about the cross-pollination across organizations. | |
| Pricing, Packaging, and Integrating with Salesforce Ecosystem | 4 | 5 | 1 | 1 | Weiss recounts Marc Andreessen's pricing advice to double the price twice and acknowledges Slack historically underpriced value. Berson prompts for lessons learned from Salesforce's sophisticated packaging. | |
| Modern Product Reviews and Cultivating High-Energy Teams | 3 | 4 | 1 | 1 | Weiss shares his format for asynchronous design reviews via clips and rejects the mini-CEO persona for PMs. Berson guides the conversation toward operational specifics. | |
| A Framework for Fast, High-Quality Product Decisions | 5 | 4 | 1 | 2 | Berson introduces a drunk-driving analogy to separate decision quality from outcomes. Weiss builds upon this with Annie Duke's concept of resulting, outlining shared context, trust, and distinguishing one-way from two-way doors. | |
| Allocating Roadmaps and De-Risking Bets through Next Hills | 4 | 4 | 1 | 1 | Weiss details portfolio allocation ratios and the metaphor of hiking to the next hill to de-risk ambitious roadmap items. Berson asks how Slack's specific allocation compares to Google's. | |
| Slack's Evolution: Balancing Product-Led Growth with Enterprise | 4 | 5 | 2 | 1 | Weiss reflects on past mistakes, including Stuart Butterfield's initial resistance to hiring salespeople and overcorrecting by slowing releases for enterprise customers. Berson asks about key inflection points. | |
| Playbook for Moving from Product-Led Growth to Enterprise | 5 | 5 | 2 | 2 | Berson highlights how common and damaging premature enterprise expansion can be. Weiss outlines the tactical PLG-to-enterprise playbook, highlighting internal account traction before bringing in enterprise sales. | |
| The U-Shaped Operating Model with Product Founder CEOs | 4 | 5 | 1 | 1 | Weiss shares his U-shaped operating model for involving founder-CEOs at early strategy and late soup tasting phases to avoid mid-cycle derailments. Berson draws on his startup network context. | |
| Outsized Influences, Sounding Boards, and Holistic Leadership | 3 | 4 | 0 | 0 | Weiss wraps up by crediting mentors who bet on his trajectory, trusted peer sounding boards, and his wife's influence on his balanced leadership style. Berson concludes warmly. |
Statements from this episode (31)
Weiss: Data solves easy product problems, but big swings require intuition
“What we used to actually say early on was, you know, data can help solve easy problems, but doesn't actually solve the hard problems. And hard problems are ones where you can't actually just experiment your way, you know, down incremental paths. You actually h…”
Slack is developing a brand new UI and navigation design
“We're working on an entirely new kind of user interface and visual design navigation for Slack.”
Weiss: Early products lack the scale for A/B testing and require intuition
“And definitely for most early products, you don't even have the scale to actually be able to say, we ran a test, we're gonna run the test for a year before you get statistical significance. You have to use intuition, judgment, strategy a lot more.”
Weiss: Slack leans 75% on data for small features, 75% on taste for big bets
“Here's what I would say is, of smaller feature work, I would say it's probably 75% data-driven, where we'll actually run an experiment or run a release with a holdback. For larger, bolder, new features that are net-new capabilities, I would say it's maybe the …”
Weiss: Consistently neutral A/B test results signal a local optimum
“And this is, I think, often a good sign that you need to stop relying on experimentation and step back, which is that every experiment wasn't really positive or wasn't really negative. It was really just neutral. And it became increasingly hard to figure out W…”
Weiss: Product taste is not innate and can be 100% learned
“My honest kind of feeling is that almost everything can be taught. That teaching may be more informal. It may be more observational. You know, product design, product intuition, I think is really about seeing what great looks like and being part of the process…”
Weiss: Product taste is learned by working with experts, not from classes
“It's something I think you learn much better by actually working side by side with folks who have really strong product taste and sensibility. And not by reading a lot, or taking some classes, or I don't know what it might be, because it's something that is in…”
Weiss: Slack scales founder product intuition via principles and 3-year strategy
“So the first is really just about making sure that we have everyone really aligned and energized around our mission, our vision, and our kind of what we call our three-year strategy internally. So that's kind of what people are aligned at a high level. But the…”
Weiss: Slack avoids endless debates by quickly prototyping functional software
“Prototype the path, which gets into how we at least approach a lot of what we do by not getting stuck in long product debates or endless design reviews, but actually figuring out what's the fastest path to being able to actually touch the software with your ow…”
Weiss: Product Teams Should Hire PMs with Distinct Spikes, Not Generalists
“No one person we hire looks like a perfect sphere. Right? So what we look for actually is people who have clear spikes on one or two of those axes, and also is well-rounded, but what are their superpowers? It's one of the things we talk about when we bring som…”
Weiss: Slack's PLG Team Launches 95% of Features as Experiments
“We have a team that's focused on more of the self-service business, this new user, new team journey, product-led growth. That team I would say, 95% of what they launch as an experiment. It's incredibly data-driven.”
Weiss: Scaling Orgs Slow Down Due to Consensus Decision Bottlenecks
“Most of the reasons why you're moving slower is because decisions start grinding to a halt. You have a consensus based kind of model. Everyone gets a voice. You don't have a framework for how you actually get to resolution.”
Weiss: Next-gen product-led SaaS companies will reach $10B within a decade
“And then I think kind of the next generation of companies like notion air table and so on, you know, these companies are all early on in their life cycle. I think give it another decade. And I think, you know, the companies that are a billion or two billion mi…”
Weiss: Bottom-up product strategy fails when executive buyers do not use software
“And so I think that's probably if I was going to delineate is figuring out this approach works best when we actually have an alignment between the end users and the people who at least can make the initial purchase decision and definitely works the worst if yo…”
Weiss: Salesforce is pound-for-pound the world's best enterprise sales machine
“In some ways, to your point, that kind of premise, if you will, of the acquisition was, if you can take the company that pound for pound is probably the absolute best at enterprise sales and marketing in the world, as in Salesforce, and you can take the compan…”
Weiss: Salesforce treats marketing messaging like iterative product prototyping
“They approach marketing in an iterative prototype driven way, the way that we've always approached products.”
Weiss: Salesforce is effectively the Berkshire Hathaway of SaaS
“Salesforce itself is almost like the Berkshire Hathaway of SaaS, if you will. Like, they are a conglomerate that has many different product lines. So they definitely have a single voice as a corporation or an umbrella brand, but all their products kind of live…”
Weiss: 77 of the Fortune 100 use Slack
“77 of the Fortune 100 use Slack, and probably a hundred of them are Salesforce customers.”
Weiss: Slack historically underpriced its product by prioritizing value creation
“I think Slack maybe, I think historically probably has underpriced the product versus the value we've created for customers. Part of that I think is one of our maxims from the very early days is we focus on value creation, not value extraction.”
Weiss: Product managers acting like "mini-CEOs" alienate their teams
“I will tell you that people who take the approach of being a mini CEO for a team are the ones who their teams wind up saying, why do we have to have a product manager on our team? Can't we do it without them? Because, you know, you can wind up accidentally bei…”
Weiss: Company strategy presentations are forgotten within a month without repetition
“If you can keep an organization aligned and focused, it's like a superpower for velocity, but alignment isn't static. You don't get to do it once. I mean, this is even if you, like, present a three-year company strategy. If you don't talk about it over the nex…”
Weiss outlines Google's 70-20-10 product portfolio allocation framework
“When I was at Google, they used to have this model they called seventy-twenty-ten, and I think they kind of classified as, you know, 70% should be, that first category you said, like, low-hanging fruit, obvious wins, incremental. 20% should be kind of extendin…”
Weiss estimates Slack's product portfolio allocation is roughly 60-35-5
“Across the board, I would say we probably look, my hunch that I haven't actually, like, actually done the math on it, is we probably look a little bit more, like, 60, 35, five, if you will. Not quite as many fully speculative things, but maybe focus a little b…”
Weiss: Multi-year product bets must be decomposed into sequential public milestones
“For any one of our large product areas, a lot of what we talk about when we're making big new investments is you have this grand vision. Okay. We're probably not going to spend the next five years building this out and then ship it and see do customers like it…”
Weiss: Slack reached $80M-$90M ARR before hiring a sales head
“I think we got to,
I want to say, 80 or ninety million dollars in ARR before we hired a head of sales.”
Weiss: Multi-billion-dollar SaaS companies cannot rely solely on PLG or enterprise sales
“If you're, you know, to your earlier kind of discussion, a multi-billion dollar company and you're building this hybrid SaaS model, you actually have to be good at both. You can't just choose one lane.”
Weiss: Target accounts with organic adoption to maximize AE productivity
“I'll tell you the best way to ramp that up is by making sure that those AEs are only talking to companies where there's already a lot of traction without ever needing a person to help them”
Weiss: PLG companies expanding to enterprise shouldn't start with outbound BDRs
“Starting off with building out a huge BDR team to do inside sales for cold leads feels like If you already had a product-led growth motion, not the right place to begin. Because I think, without a doubt, the best leads aren't ones that you cold emailed or that…”
Weiss: 85% of Slack Enterprise Deals at IPO Originated from Self-Service
“I don't know what the latest set is, but I know when we went public, we had a sat, I think it was 85% of our enterprise deals by the time we went Public at our IPO had started off as paid customers through self-service, meaning that they literally got to the p…”
Weiss: Product founder CEOs should follow a U-shaped involvement model
“If you think about like a major product initiative, not an experiment, but something more significant, that's like this big kind of bet. And you think about the X axis is kind of the time that goes on from the project starting to maybe launch. And the Y axis i…”
Weiss: Google was notorious for demoralizing eleventh-hour launch cancellations
“Or the absolute worst thing, and this happened at Google all the time, they were notorious for this, is like launch, Readiness review something or other. And you did all this work. You maybe worked for years as a team. And it's like, finally, you have one of t…”