How Contently CEO Pearl Collings grew Contently to $53.8M revenue and 300 customers in 2024.

good morning everyone my guest today is shane snow he's an award-winning journalist celebrated entrepreneur and the best-selling author of smart cuts he's also author of the forthcoming book dream teams as well as the co-author of the storytelling edge he co-founded the content technology company contently which helps creative people and companies tell great stories together and serves on the board of the contently foundation for investigative journalism shane are you ready to take us to the top i am ready so you know this about me most authors i you know say no to because they just want to promote a book and it's frankly very boring and i just eat them alive but you i made an exception for because you come from a sas background you come with a software background so tell us quickly about contently and then i'm gonna go why on earth do you decide to write a book this is like the most difficult thing ever instead of doing contently so contently didn't start as a sas platform it started as a marketplace kind of a newfangled talent agency to help you know laid off journalists from the new york times connect with clients turns out that the most profitable clients the most interesting clients when we launched about eight years ago ended up being brands wanting to do content marketing which was starting to become this popular thing and so as we leaned into that we by necessity had to start building project management tools to help these brands who are connecting with our marketplace and then that became the business it turned into this full-blown sort of like sales force for content marketing uh for for managing everything about your content uh program and that's turned into sort of the content operating platform that helps companies not just with content for marketing but for hr and a whole bunch of other things so that's the very quick sort of back story but we we actually had a point where we were going to have the the software portion be free and be subsidized by the uh the marketplace and we got in this big argument and and the argument was solved by uh my partners and i was deciding to do a test to start selling some features of uh of the project management tool uh for a monthly fee of a thousand dollars and when we sold 13 in the first month we said okay uh this is the the business and and here we are well what do people get for a thousand bucks a month was it like a number of words or number of articles or what uh back then when we started it was uh it was sort of workflow so you want your pr people and your lawyers to weigh in on your content you're about to publish now there's a there's a you know packages and tiers but it's everything from analytics document analytics sort of more hardcore workflow integrations and everything you could think of sales and environment tools um so it's kind of everything you'd want to do to uh to organize content in a big enterprise um so yeah depending on the size of your enterprise number of seats it very much kind of mimics that standard uh kind of marketing automation type of sas product only it's content rather than than uh email and would you say you're still kind of enterprise folk like what's the average customer pay per month is it a couple thousand uh six to ten thousand oh yeah so very much enterprise space high volume yeah yeah and that'll change at some point but that's where we are now okay good and before we move on to the book can you give me a general sense of scale so i know you raised capital how much have you raised and can you generally share team size things like that yeah uh so we've uh the company's about eight years old we've raised uh 20 million dollars in total which is about a quarter of any of our competitors um which is great for us because we're you know similar size and and have an outsized present and presence in our own content marketing staff is about 100 people um and um yeah what else did you ask how many customers how many customers are you working with now uh we have a couple hundred uh enterprise customers we have uh one group like i alluded to that will change at some point we have a group of customers that we call high-growth uh customers so smaller companies that are paying a lower average and uh i forget what the number is but that's that's a big growing category for us as well okay surprise and nor north or south of 20 million in arr uh it's about at 20 million look at that man i'm on fire this morning good guess okay so you're sitting on this rocket ship you're eight years in started as a marketplace you shift the model you're now serving 300 enterprise customers paying calls six grand a month call it 20 million ar right now why take time out of your schedule to write a book uh so a couple of reasons you know one is i think of my identity as a journalist i'm a journalist who ended up starting this company with a couple of partners i wrote about business and technology and science and so you know i i was covering companies like mine is now um and uh and so when we started this company it's in you know the field of media and content which is my industry uh so it's a natural thing to sort of fall into but as we started growing the company i realized that i had deficits in terms of uh you know how to build an innovative company and so my first book i wrote basically i interviewed people and i took a tour of history and psychology to try and understand how breakthroughs happen how innovation happens and find patterns for how we can do that so the writing the book was an outgrowth of my journalism work that was an excuse to help our company get better the second book that i co-authored is about our industry it's about using storytelling to build relationships and build companies um and this new book dream teams sort of a similar thing um it's sort of this itch that i've had for a long time as my role went from being the guy who did stuff right every founder you know ends up you know you you paint the walls and you take out the garbage and you write the code and you do everything uh my role went from that to the guy who picks people to work together and then has to help them work together better and seeing as the team grew you know things slow down as as organizations get bigger it's sort of natural people start having problems with each other and casting the right group of people to work on problems becomes really important and realizing that i can't make every decision myself i have to empower people with information to make decisions so i've became sort of obsessed with this as a new role that i have that i suck at so similarly let me take a tour of history and uh and the other thing too is part of what i was looking at is just the way the world and our society is sort of changing now because of technology communication and you know just politics is getting very strange i was concerned with the idea that we need each other to do anything great to make progress and yet we prevent progress because of each other and so i kind of wanted to take a meta look at you know human collaboration and the dynamics that help a team in business exceed the sum of their parts or slow down or destroy itself and how that same thing plays out psychologically in society and politics in art and entertainment all those sorts of things so that became the the genesis for the the book um part of what happened also i've been doing research i've been interviewing uh people and doing my sort of obsessive weekend and night thing um but i realized that i was not the right person to take our company from you know the 15 million to 100 million you have shane you have co-founders all right how many co-founders i do i have two co-founders yeah once the business guy once the tech guy i was the marketing guy um and then content guy so i realized that i was not the cmo that was going to take our company to the next step function so i hired a replacement and uh and after a month of getting her up to speed i wanted people to stop going around me um and and really for the mantle to fall on her and so i took a two-month sabbatical to kind of write for 14 hours a day and and finish this book so i i took some time off to step back and do this and then came back and and kind of became the consultant to her organization rather than the boss and so that's how i managed to do both these things well coming up we'll talk about why chrysler failed while wu tang succeeded and some other surprising factors behind mergers marriages and partnerships well also i'll talk to you i know you talk about the wright brothers a lot and what their daily arguments can teach about group problem solving so shane we'll talk about both those things but real quick just since facebook's hot right now in the news you've got sheryl sandberg to do your afterward tell us how you got her to agree to that and and why she liked the book um so i helped out cheryl and adam grant with their book launch option b which is the book that was kind of inspired by the you know the tragic untimely death of her husband um and they wrote about uh resilience and getting through hard things and and they reached out to me asking if cause i'm a linkedin influencer if i could write about a time when i had to be resilient to get through something and and promote their book through that so i wrote probably the most difficult blog post of my life about uh and you can find it pretty...