Trello

In today's SaaStr insider episode SaaStr CEO and Founder Jason Lemkin catches up with Michael Pryor, the Co-Founder of Trello to talk about going upmarket, and how things have changed in the last decade as Trello crosses 50M+ users. Video and blog post: https://www.saastr.com/going-upmarket-and-how-things-have-changed-in-a-decade-at-trello-with-founder-michael-pryor/

Michael Pryor

Co-Founder

TrelloAtlassian

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.

Michael Pryor

Co-Founder

TrelloAtlassian

Kolton Andrus

Founder & CEO

Gremlin

Dylan Serota

Founder & Chief Strategy Officer

Terminal

Rachel Carlson

Co-Founder and CEO

Guild Education

Sid Sijbrandij

Co-Founder and CEO

GitLabKilo Code

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

Michael Pryor

Co-Founder

TrelloAtlassian

JD Peterson is CMO of Trello where he heads the company's marketing and customer service teams. A true child of Silicon Valley, J.D. has been helping startups for nearly 20 years. Before Trello, he held positions as the CRO and interim CEO at Scripted, the VP of Marketing at Zendesk, and the VP of Products at Marketo. JD takes pride in building world-class teams, helping companies accelerate growth, and ensuring the customer remains at the center of every strategic effort. In Today's Episode You Will Learn: How did JD make his slightly unconventional entrance into the world of SaaS? Having picked Marketo and Zendesk, what does JD assess when picking companies? Once picked, how does JD evaluate culture? How does JD measure this? How does JD approach lead qualification? How does JD measure the effectiveness of lead generation, revenue or amount of leads? How does JD unify the sales and marketing team? JD has previously said that now is 'the best but hardest time to be a marketer'. Why is this and what is behind this thesis? What are the pros and cons of the data driven marketing world? What are the commonalities among the best marketeers? JD has seen many companies scale into hyper-growth, when does JD believe is the right time to hire and expand aggressively? What roles should be filled first? What does JD optimize for in the hiring process? When is the transition point needed to have a VP? 60 Second SaaStr Is SaaS marketing B2B or B2C? What does JD know now that he wishes he had known in the beginning? Biggest mistake companies are enacting with their current marketing plans? 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 JD Peterson

JD Peterson

CMO

Trello

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 Join 5,000+ SaaS founders: https://saasclub.io/email

Michael Pryor

Co-Founder

TrelloAtlassian