Hey John! Let’s start with a quick intro - what’s your current role + what’s Draft all about?
I'm John, the Co-Founder and COO at Draft. Draft powers content creation for a lot of businesses by connecting them with the best content creators for their industries and projects. So we essentially operate a marketplace where we match the supply (creators) with demand (businesses) to make creating content seamless and easy.
We also focus on a lot of tooling that wraps that whole ecosystem together, whether it's tools that help you nail your content strategy, manage content projects more effectively, or even understand how to distribute it a lot better. Ultimately, we’re building a platform to handle end-to-end content strategy and execution.
What is the origin story for Draft? Where did you get the idea?
As with most startups, it started by solving our own pain point. When we would work on a lot of other ideas, myself and my co-founders, Naeem and Vasil, would always find ourselves leaning on content as a growth pillar. We would try to get content created, put it out in different channels and try to get it to drive demand.
The process was incredibly painful. Naeem, who was previously leading growth at Zapier, saw firsthand how even at a larger organization it was hard to scale content programs. When your business is really small, you can write it yourself and knock out a content piece here or there, but suddenly when it becomes a channel you want to invest in, there's a huge bottleneck in the creation process. After struggling with this process we simply asked ourselves: why isn't this as easy as requesting an Uber? Why can't I just plug my content idea into a platform, and then two or three days later, get really good, high-quality content back?
We felt the pain, so we decided to hack together a prototype and it turned out to be a challenge that resonated with a lot of other people.
Why is content an important area for businesses to invest in?
The way we like to think about it is the world used to be focused on Google ads and Facebook ads, with businesses just getting in front of people, trying to grab five seconds or even less of their attention and hoping they click through, land on their site, and give them some money.
But as major ad platforms become more crowded and the death of cookies approaches, the business world will lean more on storytelling and education. The best way to get that across is through content. It’s also a very cost effective way to grow, so the category has already seen a lot of growth because of that.
Airbnb is a very famous example of a company investing in content. During COVID they took all their performance marketing budget and reinvested it into brand and content because the ROI on it is so much greater.
We don't see that going away. We don't see people disengaging from content. So the pressure to make high quality content will only get stronger over the next couple of years. We're riding that wave and helping to make it easier for businesses to execute their content strategy.
What would you say have been some of your own challenges with scaling of business?
At the beginning of 2021, we were a team of three. Less than two years later, we are a team of 55. Through that process we went from Seed stage to Series A. I'd say it’s been a bit of a traditional hyper-growth journey. Our ARR essentially doubled through the process of this, so we’ve seen a ton of scale challenges across the board.
I think the number one lesson that I've learned from all the growing pains is that it's incredibly important to be focused. When you have so many moving pieces in a business and you're essentially “building the plane while you're flying it”, a lot of focus as a leader needs to be on:
- How do you set the right priorities?
- How do you remove as many distractions as possible?
It is very easy to get distracted and be tempted to do multiple things in the hopes of achieving growth.
What does staying focused and removing distractions look like in practice?
We’ve taken a step back to look at our strategic planning process more clearly. It’s easy to go down this path of establishing a lot of processes and overcomplicating OKRs and trying to do everything exactly by the book in terms of running a company.
But when you’re at an early stage, it really comes down to:
what are the two to three things that the business very critically needs to achieve in order to get to that next milestone? Whatever the milestone may be, whether it's a revenue goal or another operating metric, the next question is: what is the simplest way that you can communicate the importance of these priorities to all stakeholders within the organization, and create alignment among them?
When you're going through hyper growth, there's a tendency to consume a lot of different frameworks and theories and make them apply to your situation. The lesson we learned is that simplicity is actually much more effective. If you can communicate a few things very clearly and align the entire organization to it, the payoff is amazing, and that’s the path we're on as a company now. We don't have a crazy OKR process. We don't have a lot of rigorous processes thrown in to help run the company. We've just made channels of communication very effective and we've made working asynchronously very easy to do.
What has been your key to success as a remote-first organization?
We've been remote since day one and part of why we wanted to be remote, even before the pandemic, was this notion that autonomy and freedom should allow your employees to pick the best way to work and that will increase performance. To help with being remote first, we’ve peppered in a few tools and guidelines here and there to help our team onboard and work together seamlessly. For example, we have an FAQ guidebook that every new hire is provided during onboarding which dictates what tool is used for what type of communication, what our principles are around things like when to choose synchronous meetings versus using an asynchronous tool such as Slack threads or Notion.
As the company has evolved through different stages, how have the metrics you’re focused on changed?
At the earliest stages typically we were most concerned with revenue growth and everything was anchored around that. However, as we grew and started to expand our team and had access to better analytics, we also started to shift what we were focused on. When we stood up a marketing and sales org suddenly, LTV and CAC became important metrics that we kept an eye on, because we were starting to invest a lot more dollars there with those teams. When we stood up a product org and a marketplace team, suddenly the net revenue retention numbers became a lot more important.
The situation we’ve evolved into at our current stage is there are three or four company wide metrics that really give us a pulse of if we are headed in the right direction. Each individual department also has their own leading metrics they are hyper focused on. For example, for the marketplace team, it might be content quality which is very important because we know that content quality drives better net dollar retention or revenue retention.
So I think as your company grows and there are more moving pieces, then you start to build a system where all of these different metrics allow you to understand if the money and the resources and the time that you're putting in are actually rolling up to that north star metric, whatever it may be.
As the COO of a startup, what exactly do you focus on, and how did you even know what you should be working on in the first place?
The role of COO, as far as I've understood it, changes with each stage. In the early stages, when we were, let's say 20 employees, the COO is really a Swiss army knife. You’re the person that has a pretty good end-to-end understanding of the business, as well as a versatile enough skill set that you can parachute in and solve the immediate problems that are happening or fill a functional gap before you can bring a specialized leader in. For example, I would be leading a function until we could hire a VP or an exec to take over. For other things, it may be a specific project or something that I would take on that you couldn't really designate to a specific function just yet.
Once you’ve stood up the organization with a leadership team in place, I think a lot of the COO’s role becomes alignment. A way of thinking about it is: with all of these metrics and all of the moving pieces in a business, you’re essentially the only person with all of the context. So, how do you feed it into an operating plan of some kind with the right system of inputs and outputs. And then your job really is to optimize it further. For example, can we find areas of inefficiency and then work with the specific leaders of that function to make it a little bit more efficient and drive alignment. That’s where the role has evolved to today.
Do you have teams that you work particularly close with on a day-to-day basis?
Finance and analytics are probably the two. My role is anchored in a lot of data, and because of that, I partner closely with those two functions. After that, it’s ensuring I have a strong relationship with all of the other leaders.
As you’ve grown the business, how do you determine what areas or teams to grow?
One lens to look at it is at the strategic level — what bets you’re placing really drives where you invest. For example, we're a very product-led organization; customers come in, they self-serve to sign up and use our product. But as we've acquired more and more customers, we're starting to see there are certain profiles of customers that are more of an enterprise audience. So suddenly, if you want to strategically lean into those types of accounts, maybe you need more of a sales capacity to acquire those customers and grow that channel. That then becomes an area of focus where for the next two quarters, we might try and set up a sales effort.
The second part is honestly just pattern matching. There’s generally a set of benchmarks for what a good Series A organization looks like, and norms for how to become Series B ready. So you follow that as well to understand the right things that you might need to do in the backend of the business to get ready for the next stage — whether it’s investing in the people org or BizOps.
Having gone through this experience, what advice would you have for founders?
I think for founders that are looking to start and are still on the path to let's say product market fit, my recommendation is to stay scrappy. Fail fast, learn from it and move forward.
Also, it’s incredibly important that you don't get distracted by everything else that comes into company building. For example, say you’ve received seed funding and you're still really not sure if you're at that stage of product market fit, don’t distract yourself with a lot of the other things that come with operating a business. Instead, just focus on customers and focus on revenue, which typically will cure everything else for you.
Once you get past that stage, now you have to set up a system that can grow with multiple functions and management and leaders. The best advice I can give is to find other founders that have gone through what you’re tackling now. Find other tenured executives that have been on the journey from zero to one or from, say, Series A to Series D, and just extract as much knowledge as you can from them. I’ve personally found that beats any book that you'll read.
You mentioned staying scrappy. What exactly does ‘being scrappy’ mean to you?
I think scrappiness is making sure you're getting the best bang for the work that you put in. When you're a really small company, your time is so scarce, so you need to focus on very few things that give you the greatest leverage in the business.
Secondly, when you do something, don't aim for perfection. Aim for 80:20 to get it there. Back in the early days of Draft, we really just focused on what we could do to move revenue further. As long as we have revenue, we can get subsequent funding to help us grow. The way to get that revenue wasn't to build the perfect systems or build the perfect features. Instead, it was figuring out: what is the most lean, minimum viable product that we can get in front of customers. Then, it’s about understanding if the next feature is valuable or not before building it. Even by the time we were around $100K in ARR, we didn’t have an app. It was just a few no-code solutions that drove a lot of our product. Only then did we actually start investing in an engineering team that built systems and features that could scale further.
What are you most excited about for the future of Draft?
At Draft today we have a pretty wide marketplace of human writers. One of the things I am particularly excited about for next year is AI content creation. We’re testing a lot of tools that can accelerate and supplement what the human writers are doing. For example, conducting research to generate higher content quality. I’m excited to be able to give a lot of those solutions to our users to ultimately help them create better content.
Throughout all of this - i.e. your founder journey + scaling Draft - you decided to join The Commons (Skillful at the time!). A couple of quick questions on that:
A) What prompted you to join The Commons?
As I started to play a more involved role in FP&A I realized I needed to 1. brush up on the fundamentals and 2. meet others in that function and build a network to lean on. The Commons and the Strategic Finance Sprint ticked both those boxes.
B) What do you think other founders can get out of the Sprints and/or community?
I'd say it's primarily the network and secondly an effective way to pick up a fundamental skill or framework but applied in context of tech orgs.
Circling back for a moment, before the days of Draft. What are the top skills you developed before launching a startup, that you’ve been able to bring into being a founder?
I think my engineering background and consulting background both helped me. As a consultant, you have to pick up expertise very quickly. When you dive in, you typically have no knowledge of the industry, so you have to learn and apply very quickly. So that's been very helpful as a founder, where 95% of the time you're tackling things that you’ve never faced before. You're learning things on the fly and hope that you're executing it well. My problem solving skillset, and ability to take very ambiguous problems and distill them down has been pretty helpful.
Any final words to share with founders?
When I talk to other founders, what always comes up is that it’s always going to feel like you’re flying blind, especially when you’re building things for the first time. It’s always resonated with me, as a founder, that there are people who have built companies before — and they were in this same spot. You might think about hiring them so they can help chart the path.
But part of what gives you that 1% chance of turning your business into something amazing is that, when you're flying blind, you might do unconventional things. And those unconventional things can be multipliers in how successful a company can become. So I see it as a positive instead of a negative. Trust your instincts in terms of the novel approaches that you might bring because you haven't gone through a traditional path of climbing the career ladder or operating a business. Don't discount that as a founder.
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