Jan 4, 2024 · 1h 5m · in-depth
The new PLG playbook | Arming the next generation of product-led companies | Oliver Jay (Asana)
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Former Asana CRO and Dropbox sales leader Oliver Jay deconstructs the structural challenges of layering enterprise sales onto a product-led growth business. He shares actionable frameworks for transitioning from individual user utility to executive value, structuring champion-driven sales motions, and timing critical enterprise market windows.
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 17.2% of the talking time here. How this is scored →
Brett as informed peer 4.3 Guest teaching 5.9 Guest disagreement 1.6 Brett pushing back 1.6
speaking balance: gold is Brett, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 56:50 Calling out flawed board revenue forecasting
Oliver Jay vigorously criticizes investors and founders who naively divide arbitrary revenue targets by average AE quota to justify hiring plans rather than assessing true enterprise product-market fit.
Hardest push from Brett ▶ 48:40 Pressing on size and vertical segmentation overlapBrett Berson challenges Oliver Jay to clarify how classical enterprise segmentation dimensions like company headcount and industry vertical integrate with Asana's motion-based Seed, Land, and Expand structure.
Biggest teaching moment ▶ 38:35 The four buyer personas frameworkOliver Jay educates the audience and host by detailing Asana's internal framework categorizing champions into Intel, Change, Executive, and Centralized agents.
Brett holds their own ▶ 1:02:34 Dissecting Atlassian's multi-buyer security motionBrett Berson showcases his own deep SaaS domain expertise by analyzing how Atlassian leveraged Jira's core workflow into security ticketing to gain new organizational entry points with minimal product modification.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Brett as informed peer | Guest teaching | Guest disagreement | Brett pushing back | Why |
|---|---|---|---|---|---|---|
| The Fallacy of Blending PLG and Enterprise Motions | 4 | 6 | 2 | 1 | Berson prompts Jay on why founder intuition about blending PLG and enterprise is flawed. Jay delivers a detailed explanation of how logical incremental decisions lead to the 'PLG trap' when organic accounts dry up. | |
| User Journey vs. Customer Journey Mindsets | 3 | 5 | 1 | 1 | Jay contrasts the consumer-like growth metrics of user journeys with the 12-to-18-month sales cycles of enterprise customer journeys. Berson largely listens and provides conversational transitions. | |
| Aligning User Value with Enterprise Value & Asana's OKR Discovery | 4 | 6 | 1 | 2 | Berson probes whether DevOps tools like Datadog break Jay's two-company model. Jay clarifies the spectrum of user versus enterprise value and explains how Asana uncovered executive value through OKRs. | |
| The SAML Security Trap and Lessons from Dropbox | 5 | 6 | 2 | 2 | Berson sharpens the conversation by asking if security-only selling creates local maxima that capped Dropbox's valuation. Jay agrees and breaks down the limitations of the 'SAML hostage play'. | |
| Asana's Go-To-Market Layers: From Inbound CS to Manager SKUs | 5 | 5 | 1 | 2 | Berson pushes into organizational definitions, noting that early inbound sales behaves more like customer success. Jay validates the framing and outlines Asana's tiered personas and manager-of-managers SKU. | |
| Selling Clarity and Timing the Enterprise Window | 4 | 6 | 2 | 1 | Jay details how Asana shifted from selling project tools to selling 'clarity' and explains the urgent competitive imperative to win enterprise before market categories solidify. Berson facilitates with chronological questions. | |
| Mapping the Champion Tree and 4 Buyer Personas | 4 | 7 | 1 | 1 | Jay lays out the four internal buyer personas in PLG enterprise navigation: Intel agents, Change agents, Executive agents, and Centralized/Procurement agents. Berson asks tactical questions on the size and structure of initial enterprise pilot teams. | |
| Rethinking Segmentation: Seed, Land, and Expand Motions | 5 | 6 | 2 | 3 | Berson asks Jay to reconcile traditional segmentation (company size and industry vertical) with motion-based segmentation. Jay explains the Seed, Land, and Expand framework and why headcount-by-size reps fail to hunt. | |
| Foundational Advice, Horizontal Traps, and Headcount Forecasting Pitfalls | 4 | 7 | 3 | 2 | Jay offers forceful criticisms of horizontal positioning traps (citing Evernote) and calls out founders and boards who back into hiring targets to avoid down rounds. Berson presses on whether founders should avoid starting PLG entirely. | |
| Analyzing Atlassian's Playbook and Leadership Mentors | 5 | 5 | 1 | 1 | Berson demonstrates deep market knowledge analyzing how Atlassian expanded into multi-buyer territory via security ticketing. Jay reflects on Atlassian's ecosystem model and credits his key mentors. |
Statements from this episode (31)
Running PLG and enterprise requires operating two completely separate companies
“Winning the enterprise is really, and winning a more traditional PLG motion, it's almost like two separate companies. I think it's a very different way you think about building product, different way you interact with customers, and certainly a very different …”
PLG companies mistakenly believe they can seamlessly blend into the enterprise
“I think the big mistakes companies make over and over again when I see is when they try to blend, they think they can just seamlessly evolve. And as they scale and Into an enterprise company. I think it's a lot more complicated than that.”
Jay: The 'PLG trap' happens when companies run out of organic accounts
“As you build the security stuff, it does unlock major expansion in, within your customer base, right? The companies where you have good organic usage, many of those companies will start paying you 25, 50, a 102 hundred K. And so you're taking in this data and …”
Oliver Jay: PLG focuses on the user journey, enterprise on the customer journey
“Enterprise, we always use the term customer journey. What's the customer journey? Who are the people in the company who receive different Forms of value along the way that eventually makes the right decision of buying your product, right? And that takes a long…”
Oliver Jay: Enterprise product feedback is ~80% field-driven, unlike PLG aggregate data
“On the enterprise side, it is largely dependent on what's coming from the field. I would say 80% probably, and then 20% is like, what, With that feedback, how can you sort of do the, fulfill your customer's job in a better way with your product, with a more in…”
Jay: Infrastructure and developer PLG tools convert directly to enterprise deals
“If I think about certain dev ops tools, think about like a data dog or the infrastructure layer, the PLG traction Directly leads to an enterprise deal, right? A small team of engineers evaluate the products. They decide Datadog is the right product to go with.…”
Jay: Pitching team productivity fails to resonate with enterprise executives
“As an executive, all I care about is driving enterprise value. And then really the only things that drive enterprise value are driving more revenue, lowering costs, risk mitigating, right, on that level. And so your pitch at that point is like, well, look look…”
Jay: Asana invested in OKRs to open enterprise executive sales conversations
“So at Asana, what we realized was a lot of companies were starting to use Asana as the framework for Goal setting and OKR setting. The reason is because all the work is actually already happening in projects and tasks in the product, and so you might as well s…”
Oliver Jay: Most SaaS companies cannot successfully emulate Dropbox's growth model
“Dropbox is a really interesting case study, and it is one that I think too many people look to emulate, but they just can't. Because what happened with Dropbox, amazing product, perfect market timing.”
Dropbox and Slack's enterprise value came from securitizing rogue employee usage
“And so Dropbox and Slack, if you ask me what's the company value, well, the company value was securitizing, in a way, the bottoms-up problem that we created for them, which is all this rogue usage.”
Only 5% of PLG enterprise customers expand beyond their organic base
“And I would say maybe five percent of your enterprise customers are able to actually leverage that access to IT's interest and security to drive a bigger deployment.”
Better execution on Dropbox Paper could have prevented Notion's rise
“One can argue there if Dropbox paper Had, you know, maybe launched at a different time or a different way, there would be no notion, potentially.”
Oliver Jay: Dropbox could have eliminated Box with better enterprise execution
“I would say, there's a scenario where there is no box, and I think that was, Dropbox could have made that happen”
Eighty percent of early tech unicorns were built on Asana
“A lot of the early unicorns, like when unicorns were still a big deal, 80% of them were sort of built on Asana.”
Inbound product-led sales roles are 70% customer success and 30% sales
“The job is realistically is 70% CS, 30% sales.”
Asana had 5% company penetration compared to Dropbox and Slack's 30%
“We didn't have the dynamic that Dropbox and Slack had where you have 30% of a company using it, especially when you go outside of the big tech companies. And so, A lot of times it would be like five percent of employee base”
PLG companies cannot rely solely on organic users for enterprise sales
“You want to go after executives, you got to find a different way to create that demand. You can't just rely on your organic user base to organically create you know, create those opportunities.”
Facebook was one of Asana's hardest enterprise deals to close
“Facebook was one of the hardest enterprise accounts for us to crack, because their V-one, like, non-mobile version was still so widely used, right, and caught tasks.”
Software category leaders eventually capture 70% to 80% of market share
“We look at every single category that's been created, it's very noisy in the beginning, but there's a period of like, there's like a two to three year window, where there's a massive competition, but coming out of that, the category leader is kinged or queened…”
Software companies cannot become category leaders without winning the enterprise market
“All categories have to go through the enterprise. All winners have to win through the enterprise. There's very few, I really can't think of many of any companies that have become the category leader without winning the enterprise.”
Jay: PLG-to-enterprise deals require four internal buyer personas
“For PLG companies moving to enterprise, what we found was one, and kudos to my team for figuring this out, I didn't coin this, my team did. First, we call them Intel agents... The next level we call them or change agents... And so those are change agents, and …”
Jay: Asana started a pilot three-person enterprise sales team from day one
“And so when I started from day one, I launched, even though my focus was building out the online sales side, I always had a pilot enterprise team. It was just three people in the beginning. And I basically took the three more sophisticated members of the team …”
Jay: PLG companies must start executive value sales concurrently with expansion sales
“Phase three starts the same time phase two starts, because it takes that much time to identify the problem, identify the path, and then start building the right team to execute that, that play. It takes a long, long time.”
PLG companies mistakenly segment sales teams by company size instead of motion
“This is something that I see a lot of PLG companies get wrong, which is they confuse segments and motions. If you take a step back, traditionally enterprise companies are set up and they are split by segments, SMB, mid-market enterprise, right? And of course y…”
Sales reps with mixed territories over-index on expanding warm accounts
“What I find is that Human behavior is very hard to change, and so human behavior will lead you to spend most of your time on those three big enterprise accounts that are already healthy, and you're just trying to milk more from them. Makes sense. And you don't…”
Jay: Asana organized sales teams into seed, land, and expand motions
“So we ended up splitting a team into seed, land, and expand. Seed is very straightforward, that's the self-service and the online sales component. Land and expand, the way I would think about it was accounts that we were trying to go after, the universe of acc…”
Notion would not exist if Evernote had executed on team-level value
“One can argue if they executed better, there would be no notion as well, right? But they just got stuck on the individual user value, and the team user value, like, they didn't really, it doesn't really, it didn't really resonate, right? The product didn't rea…”
The bottleneck for PLG enterprise sales is product-market fit, not headcount
“And I think for PLG companies that are moving into enterprise, your likely bottleneck is not number of heads, number of AEs. Your likely bottleneck is how many companies do you actually have real product market fit on a large scale?”
Very few PLG companies outside of DevOps have truly broken out
“There really aren't many successful PLG companies outside of like the DevOps ones like Datadog and Atlassian that have actually really broken out.”
Attempting to build a better Jira is like trying to replace Salesforce
“I think a lot of companies are trying to be like the better version of Jira. To me, that's like being the better version of Salesforce. It's going to be really hard to do and replace.”
Atlassian had a much shorter route to CIOs than Asana did
“The edge that they had was eventually the route to the CIO, the CTO to then just, all right, let's just Deploy this across the whole organization. That path is very short. Whereas for many PLG companies like us on the distance was really long.”