10 of The Top Product Led Growth Sessions From SaaStr Annual: DropBox, Postman, ClickUp, Notion, Grammarly and More!!

If you work in SaaS long enough, you start to realize that “product-led growth” isn’t just a buzzword it’s the unofficial dress code at SaaStr Annual. Everyone is talking about free trials, activation rates, product-qualified leads, and that one onboarding experiment that magically doubled conversion overnight. SaaStr has been a kind of live laboratory for product-led growth (PLG), hosting talks from teams at Dropbox, Postman, Notion, Grammarly, and dozens of other companies that have turned “try the product” into a full go-to-market engine.

In this guide, we’ll walk through 10 of the top product-led growth sessions from SaaStr Annual and related SaaStr programming the talks that keep getting shared, quoted, and rewatched because they’re packed with highly practical lessons. Think of this as your curated PLG playlist: what to watch, what to steal, and how to apply it whether you’re running a scrappy seed-stage startup or scaling past $100M ARR.

First, a Quick Refresher: What Is Product-Led Growth?

Product-led growth is a go-to-market strategy where the product itself drives acquisition, activation, expansion, and retention. Instead of relying primarily on outbound sales or big marketing campaigns, you design the product experience so new users can discover value quickly, fall in love with it, and naturally move into paid plans or higher tiers.

The term really took off around 2016, when OpenView partner Blake Bartlett started popularizing PLG as a distinct motion in SaaS. At SaaStr Annual 2017, he outlined traits of successful PLG companies viral distribution, self-serve onboarding, and pricing that matches customer value themes that still show up in today’s best sessions.

Modern PLG isn’t just “free plan + cute mascot.” It’s a disciplined system:

• Design a friction-light path to value (signup, onboarding, first aha moment).
• Use product data to guide lifecycle messaging and in-app prompts.
• Turn usage into revenue via upgrades, expansion, and cross-sell.
• Layer sales, success, and community on top once you have traction.

SaaStr Annual is where many of these ideas get battle-tested in public. Let’s dive into 10 standout sessions and the PLG lessons they unlock.

10 Must-Watch Product-Led Growth Sessions From SaaStr

1. Beyond Product-Led Growth: 7 Lessons in Product-Led Scaling – Dropbox

Dropbox has been a PLG poster child for more than a decade, so when its leadership sits down with SaaStr to talk “beyond product-led growth,” you pay attention. In this session (and the companion SaaStr Podcast #490), Dropbox’s GM walks through seven lessons learned moving from PLG to product-led scaling.

Key takeaways:

• Virality is a great start, but expansion revenue comes from deeply understanding team and enterprise use cases.
• You need to redesign packaging and pricing as customers move from solo users to full company deployments.
• PLG doesn’t replace sales it feeds it. Sales should focus on high-value accounts already lit up with product usage.

If you’ve hit a plateau on freemium growth and are wondering “What now?”, this session is your blueprint for graduating from cool product to durable business.

2. Building a $5.6B Company With a Product-Led Flywheel – Postman

Postman’s story is the ultimate developer-tools PLG flex: a widely adopted free tool that evolved into a multi-billion-dollar platform by listening obsessively to users and watching what they actually do in-product. At SaaStr, CEO Abhinav Asthana explains how community, product, and data combine into a product-led flywheel.

The flywheel looks something like this:

• Individual developers adopt the free product to solve a specific workflow problem.
• Usage data reveals patterns across teams and companies.
• Postman builds collaboration features and governance for teams and enterprises.
• Community events and content feed more adoption, creating a reinforcing loop.

The lesson: PLG is not just a funnel; it’s a loop. The more your users do, the smarter your roadmap becomes and the more value you can deliver back to those users.

3. How Community-Led Growth Drives Product-Led Growth – Notion

Notion’s CRO Olivia Nottebohm has a simple thesis: at the heart of PLG is the user, and one of the best ways to serve those users is through community. In this SaaStr session, she shows how community-led growth and product-led growth reinforce each other.

Notion’s community helps:

• Onboard new users with templates, tutorials, and workflows created by power users.
• Surface niche use cases that the core team might never think of.
• Create social proof that encourages teams to standardize on Notion.

For your own product, the takeaway is clear: if your users are creating content, extensions, or playbooks around your product, that’s not a side project. That’s part of your product-led growth engine treat it like one.

4. Mastering the Art and Science of Product-Led Growth – Gainsight

While Gainsight is often associated with customer success, it also leans heavily into PLG, using its own product to drive adoption and expansion. In a popular SaaStr podcast session, Gainsight’s leadership breaks PLG into “art and science”: the art is building a product users love, the science is instrumenting every step of the journey.

They emphasize:

• Tracking product signals (logins, feature usage, collaboration events) to identify product-qualified leads.
• Feeding those signals into lifecycle campaigns and sales workflows.
• Using in-app guidance and CS motions to turn “activated” into “retained and expanded.”

The big idea: PLG without measurement is just vibes. Instrument first; experiment second; scale what works.

5. Calendly’s Journey in Product-Led Growth – Hybrid PLG + Sales

Calendly is another SaaStr favorite, frequently discussed on the official SaaStr podcast for its skillful blend of viral product mechanics and enterprise sales. Their story illustrates how a simple, self-serve product can become an enterprise platform when you pay attention to who’s inviting whom, and where usage is spiking inside organizations.

Calendly’s motion:

• Make the free experience so delightful that users literally send it to colleagues and customers.
• Detect when multiple users at the same domain are active and propose team plans.
• Add admin, security, and integrations layers that justify an enterprise sale.

It’s a masterclass in using self-serve adoption as a leading indicator of where to point your sales team.

6. Product-Led Growth Playbook for B2B Startups – Mark Roberge

At SaaStr Annual 2022, Mark Roberge, former HubSpot CRO and author of the PLG Playbook for B2B startups, shared how to optimize go-to-market for PLG businesses. His sessions often highlight how PLG changes the math on pipeline, pricing, and unit economics.

A few of his core messages:

• Your “demo” is now your product. Every friction point in onboarding is a leaky part of your funnel.
• Sales should be built on top of usage, not in parallel to it.
• Pricing experiments should be constant, but always anchored in how customers actually use the product.

For founders, this session is like a calibration tool: are you still thinking about go-to-market like it’s 2012, or have you updated your mental model to PLG-era realities?

7. 5 Traits of Successful Product-Led Growth Companies – Blake Bartlett, OpenView

Technically from SaaStr Annual 2017, this talk has aged weirdly well like a good meme or a fine API. Blake Bartlett breaks successful PLG companies into a few recognizable traits: end-user focus, viral loops, low-touch onboarding, consumer-grade UX, and pricing transparency.

He also notes that the best PLG products are often discovered “sideways”: through word of mouth or in-product invites, not cold calls. If your acquisition strategy still depends mostly on SDRs, this talk will make you rethink where your next 10x comes from.

8. PLG + SLG: Hybrid Go-to-Market Strategies From SaaStr 2022–2023

A big shift in more recent SaaStr events has been the move from “PLG vs. sales-led growth (SLG)” to “PLG and SLG.” Multiple sessions and recap articles highlight that as PLG startups scale, they almost always add a sales motion on top, especially for mid-market and enterprise.

Common themes:

• Use PLG to win the bottom-up, then sales to orchestrate the top-down deal.
• Design your product experience so it still works if a champion brings in procurement and security.
• Revenue efficiency improves when sales talks to customers who already love the product.

If your board is asking whether you’re “PLG or sales-led,” this body of SaaStr content suggests the correct answer is “yes.”

9. Scaling Revenue With Product-Led and Enterprise Growth – Confluent

In a SaaStr Annual 2022 session summarized by several event recaps, Confluent’s president Erica Schultz talked through scaling revenue in a changing macro environment. A core insight: you can design a modern customer experience that combines product-led adoption with enterprise-grade relationships.

Key ideas:

• Revisit personas as your product expands so marketing, product, and sales stay aligned.
• Create a consumption-based culture, not just a usage-based price list.
• Use product data to prioritize where high-touch investment actually pays off.

It’s a great session if you feel stuck between “self-serve” and “enterprise” and want confidence that you don’t have to pick just one.

10. Developer-Led Growth as a Form of PLG – Developer Tools at SaaStr

One SaaStr perspective that doesn’t get enough airtime outside the conference is “developer-led growth,” a flavor of PLG especially common in API-first and developer tools. A popular write-up referencing SaaStr content notes that many of the fastest-growing products in the keynote were developer-focused, with self-serve as the default entry point.

The pattern:

• Start with an individual developer solving a specific problem.
• Earn trust by being reliable, well-documented, and fast.
• Expand into team and organizational features once usage consolidates.

If you’re building for developers, this lens is essential: docs, SDKs, and sample apps are not “marketing assets” they are your PLG motion.

Big Product-Led Growth Themes Across These SaaStr Sessions

Once you zoom out, the same PLG patterns keep popping up across Dropbox, Postman, Notion, Calendly, Confluent and others:

• Start with a sharp, end-user problem. Every winning PLG story starts with one clear use case (share files, schedule meetings, test APIs, organize knowledge) that delivers value in minutes, not months.
• Make activation ridiculously obvious. Great PLG products minimize fields, clicks, and cognitive overhead between signup and “Oh wow, this works.”
• Instrument everything. From Postman’s flywheel to Gainsight’s data-driven PLG, the best teams treat product usage as the backbone of their CRM and lifecycle marketing.
• Design for expansion early. Notion, Dropbox, and Calendly all bake in sharing, collaboration, and admin features that make it easy to grow from one user to one department to one company.
• Layer in sales at the right time. Almost every “pure PLG” success eventually adds sales, customer success, and partner motions once there’s enough usage data to justify higher-touch investment.

In other words, PLG is not a phase; it’s the operating system for the whole company.

How to Turn These SaaStr Sessions Into Your PLG Roadmap

Watching a stack of SaaStr talks is great. Turning them into a roadmap is better. Here’s a simple way to apply what you’ve just learned:

1. Audit your current product journey. Map the steps from “I’ve never heard of you” to “I’m a paying power user.” Where does friction pile up? Where do people drop off? Be brutally honest.
2. Design your first “aha in 5 minutes” path. Borrow from Dropbox and Notion: what is the one action that best predicts long-term value, and how can you get new users there in as few steps as possible?
3. Instrument key PLG metrics. Track signups, activation, time-to-value, product-qualified leads, expansion, and net retention. Gainsight’s framework is an excellent mental model here.
4. Build a light-touch, data-driven sales assist. Start with small motions: have one rep or founder follow up on high-intent accounts already active in-product, rather than blasting cold outbound.
5. Invest in community and content. Steal a page from Notion and Postman: amplify user-generated content, publish playbooks, and create spaces where your customers teach each other how to win with your product.

If you’re stuck on any of these steps, treat the 10 sessions above as your crash course. Watch how the leaders describe their evolution over time especially the messy parts and borrow liberally.

Experience: What You Learn After Binge-Watching PLG Sessions From SaaStr

After you’ve watched a dozen or more SaaStr PLG sessions back-to-back (highly recommended, maybe with coffee and a pause button), a few more “lived experience” lessons start to emerge.

First, nobody gets PLG right on the first try. In almost every story, there’s an early phase where the team thought the magic moment was Feature A, only to discover through data and customer interviews that users actually cared most about Feature B. Dropbox experimented endlessly with sharing flows; Calendly refined how and when to prompt for upgrades; Postman iterated on how to nudge individual developers toward team collaboration.

Second, PLG is way more cross-functional than the slideware suggests. The reality behind the scenes is messy in a productive way: product, design, engineering, marketing, sales, and customer success all need to agree on the same definition of “value.” When you hear Confluent or Gainsight leaders talk, you’ll notice they’re rarely describing PLG as a “product project” it’s a company strategy that changes hiring profiles, squad structure, and even how customer success is compensated.

Third, your onboarding is a mirror. If your sign-up flow is long, confusing, or asks for a credit card before delivering value, you probably have internal misalignment: maybe finance is nervous, or sales is worried about cannibalization. SaaStr speakers gently (and sometimes not so gently) point out that the fastest-growing companies are the ones willing to let users experience real value before revenue shows up. It’s scary at first then you see activation and conversion climb, and you wonder why you didn’t start earlier.

Fourth, hybrid PLG + sales is the norm, not the exception. Listening to SaaStr 2022–2023 recaps, you’ll struggle to find a serious SaaS company that is purely one or the other. Early on, the pendulum swings toward PLG because you need usage and feedback. Later, you bring in sales and partners to unlock larger deals, multi-year contracts, and more complex use cases. The art is not choosing sides; it’s orchestrating the handoffs so users never feel like they’ve left the product experience and entered a bureaucracy.

Finally, the emotional arc of PLG is very real. Founders and leaders talk about the anxiety of “giving the product away,” the frustration of watching early experiments fail, and the joy of opening a dashboard to see that a feature you shipped last week is suddenly being used by thousands of people. That emotional journey is part of the work. PLG is not just a set of tactics; it’s a commitment to trusting your product and your users enough to let them lead.

If you internalize those experiences, the SaaStr sessions become more than talks. They feel like advice from future you the version who has already navigated the tradeoffs of freemium vs. paid, sales vs. product, virality vs. focus, and come out the other side with a more resilient, user-centric business.

Final Thoughts: Why These 10 SaaStr PLG Sessions Still Matter

The tools, markets, and AI-powered everything will keep evolving, but the core PLG lessons from Dropbox, Postman, Notion, Calendly, Grammarly’s peers, and other SaaStr favorites are surprisingly durable: obsess over user value, remove friction, design for expansion, and let data guide where humans add the most leverage.

Watch these sessions with a notebook open, pick one or two ideas to test in your own product this quarter, and you’ll already be ahead of most of the market. Product-led growth isn’t magic it’s just relentless focus, applied where it matters most.