Nov 8, 2020 · 51m · saastr
Going Upmarket, And How Things Have Changed in a Decade, at Trello, with Founder Michael Pryor
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gold bands on the timeline = statements, start to end. Hover to read, click to jump. CC turns on captions
In this SaaStr conversation, Jason Lemkin interviews Trello co-founder Michael Pryor on Trello's decade-long evolution, exploring product-led enterprise growth, maintaining radical simplicity, adapting to asynchronous remote work, and building enduring SaaS brands.
How this conversation actually went
Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. Jason holds 25% of the talking time here. How this is scored →
Jason as informed peer 6.0 Guest teaching 4.9 Guest disagreement 1.6 Jason pushing back 3.1
speaking balance: gold is Jason, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 16:57 Pryor challenges the enterprise self-service assumption
Pryor pushes back against Lemkin's assertion, pointing out that six-figure enterprise buyers do not simply swipe credit cards and inevitably require human sales support.
Hardest push from Jason ▶ 16:30 Lemkin's self-service rule for enterprise foundersLemkin directly challenges conventional enterprise software logic by insisting that every app must build a self-service funnel to ensure product usability.
Biggest teaching moment ▶ 21:51 Maslow's hierarchy of collaboration toolsPryor reframes Lemkin's question about standalone apps by constructing a clear conceptual hierarchy of workplace needs with chat as the foundational layer.
Jason holds their own ▶ 41:47 Lemkin counters on async sales coaching toolsLemkin uses his domain expertise on sales tools like Gong and Chorus to counter Pryor's claim that sales mentorship requires in-person proximity, leading Pryor to change his mind.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Jason as informed peer | Guest teaching | Guest disagreement | Jason pushing back | Why |
|---|---|---|---|---|---|---|
| Welcome and Trello's Early History | 5 | 2 | 1 | 1 | Lemkin opens the conversation warmly, recalling his early 2012 review of Trello and noting Trello's evolution to FedRAMP compliance. Pryor engages in lighthearted banter about user rankings without tension. | |
| Designing Simplicity and Advanced Views | 5 | 6 | 1 | 2 | Pryor provides an in-depth conceptual breakdown of product design, comparing feature expansion to managing an application's vocabulary and grammar. Lemkin asks how Trello balances this simplicity against the complexity needed to win enterprise deals. | |
| Asynchronous Collaboration and Low Friction | 5 | 6 | 2 | 3 | Pryor explains the rise of asynchronous video and Trello's effort to lower horizontal onboarding hurdles compared to heavy vertical software. Lemkin interjects with humorous quips about Loom's rapid market capture and enterprise training overhead. | |
| Debating Enterprise Self-Service Models | 7 | 5 | 3 | 6 | Lemkin presents his strong thesis that every enterprise product must have a self-service tier to force product usability. Pryor agrees with the friction-reduction benefit but notes the realities of high-touch enterprise buying and sales-led overhead. | |
| The Hierarchy of Workplace Collaboration Tools | 6 | 6 | 1 | 2 | Lemkin asks whether standalone web destinations are being supplanted by chat ecosystems like Slack and Teams. Pryor reframes the collaboration landscape into a Maslow's hierarchy of needs, positioning real-time chat at the foundational bedrock. | |
| The Mechanics of Viral Collaboration Software | 5 | 5 | 1 | 3 | Pryor breaks down viral product dynamics, explaining that bottom-up collaboration tools succeed when individual end-users retain utility across work and personal life. Lemkin probes whether viral growth hits a ceiling at massive scale. | |
| Pandemic Acceleration and Distributed Realities | 7 | 5 | 1 | 3 | The two analyze the March 2020 pandemic surge, debating whether rapid SaaS growth was a temporary pull-forward or a permanent step function. Lemkin offers market analysis on institutional trust flight and e-commerce substitution. | |
| Virtual Presence and Asynchronous Mentorship | 8 | 4 | 2 | 5 | Pryor initially argues that sales mentorship requires physical co-location and osmosis. Lemkin pushes back citing digital conversation intelligence platforms like Gong and Chorus, prompting Pryor to concede that async digital mentorship can actually outperform in-person habits. | |
| Software Brand Longevity and Future Vision | 6 | 5 | 2 | 3 | Lemkin raises the question of brand longevity in software over decades, pressing Pryor on Trello's viability into 2030 and 2040. Pryor explains that while technical building blocks become commoditized via APIs, long-term value resides in customer brand trust. |
Statements from this episode (12)
Pryor: Trello's user base is well above 50 million users
“What's gotten us to that fifty million number, which At this point is a really old number, but you know, because big companies, but yeah, public companies, there's some schedule to when you can say these numbers, but it's a lot higher than that now.”
Pryor: Horizontal SaaS tools must keep terminology minimal to lower onboarding friction
“I think when you're building a horizontal tool like Trello, that's our job is to say, keep that dictionary really small and make sure that the ramp to understand the application is as low as it can be for people to onboard.”
Pryor: Product managers mistakenly treat confusing feature design as user education problems
“But I think the behavior that happens a lot of times is PMs get in there. They add the feature because they just need to do it. And so they just build it. They build it in a new, you know, space, they give it a term. And so then this problem comes where it's l…”
Lemkin: Enterprise products need self-service to enforce product usability
“No matter how enterprise your app is, it should have a self-service component. Because if it does, you will be able to figure out how to get to the atomic element of this app without training, right? If you have no self-service, you can skip, you can have as m…”
Pryor: Atlassian sells enterprise software with a tiny sales headcount
“There's the companies that are like, I build enterprise software, and then 60% of the people that work at the company are enterprise salespeople. Right. And then there's other companies where you have a tiny percentage of the company is the sales team, but the…”
Lemkin: Most enterprises have over 1,000 cloud apps deployed
“Most enterprises have over a thousand cloud apps deployed, right? Most departments have over a hundred”
Pryor: Chat communication is the foundational layer in workplace software
“I think really it's like more like, you know, Maslow's hierarchy of needs, right? Like, and at the base layer is this, is the chat communication layer. It's like, it's the bedrock. Like that's where people just start and they need that. And then they start to …”
Pryor: Collaboration tools fail unless every team member buys in
“I think like any kind of collaboration app that you have is subject to Like the weakest link, I'll say, you know, it's like in order for it to succeed, everyone has to buy into it or it's not going to work.”
Pryor: Trello Signups Surged 75% Year-Over-Year in March 2020
“This March, Versus last March, I think signups were like, 75% higher this March than they were the prior March from the year before.”
Lemkin: Every Trusted Brand Has Benefited From Pandemic Flight to Safety
“Every trusted brand has gotten a boost.”
Pryor: Seating junior sales reps beside top performers accelerates ramping
“I think like we saw this a long time ago at Stack Overflow when we were hiring salespeople, if we would put Physically just put a junior salesperson next to somebody that was really good. Like just sit them seated at their desk next to somebody that over time,…”
Pryor: Software brand longevity comes from customer relationships, not specific tools
“Like that's the connection with the customer is what's inherent in the brand, not necessarily the tool itself and something that jobs that you solve for people today might be completely different jobs that you solve for them next year.”