Rebuilding Draft.dev for 2026 and Beyond
As a company, Draft.dev has been a wild ride.
I started the company in 2020 and by 2022, we were doing $2.5m in revenue and I had a whole team working to create hundreds of pieces of developer-focused content every month.
I stepped back, and started working on a bigger vision. I bought a second company and started to apply the framework I had built at Draft.dev at The Podcast Consultant, and within a year and a half, I was out of the day-to-day in that business too.
In 2024, things at both businesses were stable, so I started to look for the next business to buy.
And Then, 2025 Happened
At the beginning of 2025, the rules for SBA lending changed, forcing us to rethink our model for future acquisitions. This is fortunately a temporary change, but it forced me to pull the plug on multiple deals that we had just started to entertain.
In the meantime, Draft.dev’s dealflow slowed to a crawl.
Part of it was the macroeconomic environment: 2025 has been a year of uncertainty in many ways, and a lot of our clients and prospects were taking a “wait and see” approach before committing to any external marketing spend.
At the same time, AI and its impact on search behavior, content strategy, and our clients’ product roadmaps introduced even more uncertainty.
Finally, the swing in talent demand meant there were more freelance software engineers, developer relations professionals, and dev marketers on the market than ever before.
The Warning Signs
While cashflow at Draft.dev stayed strong through Q1, the leading indicators showed that we weren’t closing the deals necessary to maintain that level of revenue into Q3 or Q4, and that meant we’d either have to revisit our cost structure, packaging, or both.
I was pretty disconnected from Draft.dev going into Q1, so while I saw that sales call numbers were down, the team assured me that they had ways to fix it. We relaunched the website, started selling a couple variations on our existing content packages, and trying new things to get more face time with our target buyers.
Unfortunately, none of it was putting enough good deals into the pipeline, so by Q2, I started taking a more active role in the problem.
Stepping Back In
Since our options for acquiring another company were limited anyway, I decided that my highest leverage point would be stepping in to help with sales at Draft.dev. In May, I started joining calls, working my personal network, and having conversations with clients and industry people to understand their demands and objections.
A few things immediately struck me as I joined in:
- The demand was fundamentally different than it was two years ago. Draft.dev has always been on the high cost, long timeline, high quality end of the value spectrum as this matched the traditional wisdom in developer marketing. But, very few prospects wanted to wait 6-8 weeks for pristine content when they could get a rough version from a freelancer in 1-2 weeks for 1/3 the price.
- We were mostly leaning on inbound. Historically, our positioning and focus has always been so strong that we didn’t need to do much intentional outbound, but we were starting to see the repercussions now. Even if outbound leads to deals with longer cycles or lower close rates, we needed to have some specific plan to leverage our networks and industry connections to drive deal flow.
- There wasn’t a clear prioritization in our prospecting or sales efforts. Instead of doubling down on larger clients we did great work for, actively maintaining relationships with previous clients, or finding new leaders to connect with, we were working every deal with equal effort - even if it was only going to net us a few thousand dollars.
- We didn’t know how to successfully execute some of the services we were selling. For months, I had been pushing the team to sell more strategic offerings, but nobody on the team really had enough experience to push back on clients who wanted us to do silly things. So, we fell into the habit of being order-takers and spinning our wheels when client’s weren’t sure what they wanted.
I take full responsibility for all of these mistakes.
This wasn’t a team failure problem or even a “hiring the wrong people” problem. Draft.dev’s product-market fit had simply expired because the market around us had changed dramatically.
While I thought I was avoiding being a micromanager, I was letting good people flounder because they didn’t feel comfortable or empowered to raise their hands and ask for help.
If I had built a culture that was more open to feedback or really pushed people to give me feedback, I think I might have seen some of these patterns earlier, but by the time I stepped back in, it was too late to fix some of these issues without a pretty big change in our team and pricing structure.
Re-Building the Sales Pipeline
The first thing I decided to do was to build up our sales pipeline again.
Sales calls had dwindled down to one or two per week, not nearly enough to sustain our model in the long-term, even with many clients on retainer and a decent close rate. So, rather than sitting on my hands and waiting for people to book more calls, I built up a target account list.
With under 400 companies, most of whom we had contacts or done previous work for, the list was small enough that I could manually work a few companies per work with a low-volume, high-touch outreach effort.
I also re-worked these calls to be less about finding a way to sell them something and instead to focus on learning about what they are doing and their concerns, fears, and challenges in the current market.
I changed our sales targets so that on a weekly basis, the focus is positive connections and calls with target accounts, not just explicit “sales” calls. This means that it’s a good week if we get 10+ opportunity calls, even if only 1-2 are “true” sales calls as the long-term goal is to nurture those opportunities rather than just take whatever interest comes in.
I also changed the sales process quite a bit. I threw out our deck and instead of walking them through set packages and pricing on the first call, I simply focused the first call on finding out if the prospect had pricing, power, and priorty (the 3-Ps) to even make scoping a project worth it.
Re-Discovering Product-Market Fit
By August, I had had enough sales calls and interactions with customers, to see that we had to rework our offerings, and fast.
The playbook that I used to build Draft.dev (long timelines, robust processes, high costs) was not meeting the needs that customers were coming to us with. I kept hearing people demand faster turnaround times, lower initial commitments, and some assurance that we’d get them the results they wanted.
So, my business partner and I decided we had to make a hard pivot if we were going to keep the company relevant in 2026 and beyond.
We went to the drawing board, and started looking at what had worked for clients who got the most value out of our work together, and started to look at other best practices that many of our clients weren’t following in their content efforts.
The Problems
These conversations and a deeper dive into our data led me to realize that many clients weren’t getting the value they should out of the content we were creating. While reasons varied, itt typically came down to one or more of the following:
- They lacked a cohesive strategy. Many clients get hung up on every single piece of content rather than looking at content marketing as a holistic effort. In other words, they put too much emphasis on every article, page, or blog post being “perfect” (a subjective target) rather than focusing on the way multiple types of content can work together to drive their goals.
- They couldn’t maintain a regular publication cadence. While we were there to help them outline, write, and revise content, their internal approval process would mire down publication workflows, leading to half the content we wrote in 2024 actually being published. This is a huge problem, because clients obviously don’t get value out of content that never sees the light of day.
- They weren’t telling anyone about the content. Because they only published sporadically and didn’t have a plan to get content in front of their target audience (or sometimes didn’t even define their target audience), there was very little chance anyone would ever find it. Sure, SEO might eventually work, but when you can only publish once or twice per month, that’s a long, slow road to take.
Rebuilding Draft.dev
After identifying the blockers, the next question we asked ourselves was, “How can we remove them?”
Fortunately, we have run successful content marketing efforts for both our businesses and we’ve seen them running at many of our clients and friends’ companies, so we knew these issues could be resolved. But, we also knew that the answer wasn’t a step-function improvement to our existing process, but rather a rewriting of how we worked with clients and our fundamental value proposition.
So, we made a huge change:
Draft.dev no longer just writes technical content.
Draft.dev builds and runs your technical content marketing engine to ensure it drives meaningful growth.
While this means that yes, we still write technical blog posts, create tutorial and demo videos, and create high-impact lead magnets, it means we only do them in tandem with a cohesive, consistent strategy, and a plan to meaningfully promote these assets.
And we don’t just trust that clients have something. We create this roadmap and promotional strategy for clients, allowing us to sit at the table while we review the results together each month. This new approach allows us to control some of the roadblocks that have traditionally held clients back from building a well-oiled content machine, and while we haven’t transitioned 100% of our clients over to the new model, the early signs are that this is the way forward for the business.
What’s in Store in 2026?
My goal as a CEO isn’t to be the “fixer,” I want to enable others to do that, but there are times when the market changes enough that you have to step in and re-engineer your business. It’s not realistic to expect a non-CEO to do that, so while I will get back to a more passive role in the business, I’m also not naive enough to think it’ll happen overnight.
The economic and technical environment is still changing quickly, and we have a lot of details to operationalize so the business doesn’t rely on me for the day-to-day again, but I’ve been down this path before. It’s not something I’m worried about doing again.