SaaStr 282: The Ultimate Guide To Remote Work; All vs Part Remote Teams, How To Maintain Culture Across Teams, Should Compensation Be Location Adjusted, How To Structure Internal Processes with Remote Teams, How Remote Teams Impact Hiring, Sales and Fundr
Michael Pryor, Co-Founder & CEO @ Trello, now Head of Trello Product with Atlassian following their recent acquisition.
Kolton Andrus is the Founder & CEO @ Gremlin, the failure as a service startup finds weaknesses in your system before they cause problems.
Dylan Serota, Co-Founder and Chief Strategy Officer @ Terminal, the startup that helps you create world-class technical teams through remote operations as a service.
Rachel Carlson, Co-Founder and CEO @ Guild Education, the leader in education benefits offering the single most scalable solution for preparing the workforce of today for the jobs of tomorrow.
Sid Sijbrandi, Founder & CEO @ Gitlab, a single application for the entire software development lifecycle.
Jeppe Rindom is the Founder & CEO @ Pleo, the simple spending solution for your company automating expense reports and simplifying company expenses.
In Today's Episode We Discuss:
How should founders think about the debate between all remote vs part remote teams? How does life and operations change with each? What are the pros and cons? Is it possible to move between the two overtime?
What can one do to maintain culture with remote teams? What processes need to be in place to ensure a cohesive and streamlined communication process? What technical architecture needs to be in place? Where are the breakpoints when it comes to communication? How often does one need to do in person off-sites?
How does being remote or part remote impact fundraising? How do VCs think about this new structure of operations? What is the right way to present it? How does being outside a core tech hub impact one's ability to raise? How should one run a fundraising process if outside a core hub?
How important is it for your team to be near your customers? How does this change according to sector and customer base? How important is it for your team to be near your investors? Does having an exec and sales team in one place and the rest of the team elsewhere work?
Jason Lemkin
Harry Stebbings
SaaStr
Read the full transcript on our blog.
SaaStr 104: Trello Founder, Michael Pryor on The 3 Key Elements That Make A Great CEO, The Fundamentals To Make A Pivot Successfully & The Secrets To Building The Most Efficient Workforce
Michael Pryor is Co-Founder & CEO @ Trello, now Head of Product with Trello at Atlassian following their recent acquisition. For those that do not know, Trello lets you work more collaboratively and get more done. Prior to the acquisition they raised from some of the best in the business including the likes of Spark Capital, Index Ventures and Box Group. Michael is also a board member at StackOverflow.
In Today's Episode You Will Learn:
How did Michael make his way into the world of startups and come to found Trello?
What does Michael believe is fundamental to making a market transition successfully? What were the challenges of the early market transition with Trello?
What does Michael believe are the 3 key elements that make a great CEO? How does Michael approach the element of cash burn? Does Michael agree for the need of sustainability within growth?
How does Michael look to continually recruit the best talent? What are the secrets to running a 60% remote workforce so efficiently?
How did the Atlassian deal come about? What was the thought process behind the sales vs raise more venture funding? How did Michael broach the process with regards to transparency within the team?
60 Second SaaStr
If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:
Jason Lemkin
Harry Stebbings
SaaStr
Michael Pryor
Product-Led Growth: Trello's Path to Millions of Users
Michael Pryor and Joel Spolsky spent 15 years building developer tools at Fog Creek Software. Then they created Trello - a product-led growth experiment that millions of people would use, including Google, Adobe, and the New York Times.
In this episode, Michael shares how product-led growth shaped every decision at Trello, from targeting 100 million free users with just 1% paying $100 a year, to designing a product so simple that users wrote their own blog posts promoting it for marketing, recruiting, and editorial workflows.
The freemium SaaS model was central to Trello's product-led growth strategy. Michael wanted 100 million people getting value from Trello, which required radical simplicity. Users started writing blog posts about how they used Trello for everything from applicant tracking to kitchen renovations. Trello never asked them to do it - the product spread through organic self-serve adoption.
🔑 Key Lessons
🚀 Product-led growth requires radical simplicity to reach mass adoption: Trello targeted 100 million users at 1% paid conversion, so the product had to be simple enough for anyone to use immediately, which meant resisting developer-specific feature requests from day one.
🎯 Product-led growth accelerates when users market for you: Trello's biggest growth driver was users writing blog posts about their own use cases - marketing, recruiting, editorial - each speaking to a specific audience without any prompting from the company.
🛠️ Side projects can outperform your main product: Fog Creek poured effort into City Desk, their first CMS product, but the bug tracker they built internally became FogBugz - the company's cash cow for 15 years.
📉 Most product experiments will fail, so run many: Fog Creek launched 13 products over 15 years. A job board for Indian programmers made 25 rupees. A $2,500 documentary series found no buyers. Only three products became significant.
🔄 Horizontal positioning is a freemium SaaS marketing problem: Trello could be used as a project manager, CRM, or applicant tracker, but having no category name made it hard to market. User-generated content solved this by showing specific use cases.
🏢 Self-fund before raising to retain control and validate traction: Fog Creek self-funded Trello for several years using product revenue before raising $10M+ in outside investment, which meant investors came inbound after traction was already proven.
Chapters
Introduction
Meet Michael Pryor
Success quote: Keep it simple
Trello overview and target customers
Before Fog Creek: Working at Juno
First product: City Desk CMS
FogBugz becomes the cash cow
Fog Creek's product philosophy
Why Trello spun off from Fog Creek
Where the idea for Trello came from
Creek weeks and innovation culture
Validating ideas at Fog Creek
Product-led growth: marketing Trello beyond developers
Positioning a horizontal product
The branding and naming challenge
How Omer uses Trello for podcasting
Trello as a flexible process tool
Fog Creek culture and values
Revenue and team size today
Why Michael became CEO of Trello
What excites Michael most right now
Lightning round
Resources
Full show notes: https://saasclub.io/32
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