How we built a documentation system from scratch for a startup
Startups move fast, sometimes too fast for their own good. New features are shipped weekly, decisions are made in Slack, and documentation often lags behind or lives in fragmented places like Google Docs, GitHub issues, or someone’s brain. For one early-stage SaaS company we partnered with, this chaotic speed was starting to slow them down.
They had just crossed product-market fit. Their engineering team was growing. Customers were signing up, but also asking the same questions repeatedly. Internal knowledge was scattered. And no one owned documentation.
That’s when we joined them to build a documentation system from scratch. A system that could grow with them, scale without becoming brittle, and support users, engineers, and customer-facing teams alike.
The Starting Point: A Maze of Mismatched Docs
According to Stripe’s Developer Coefficient Report, developers spend over 17 hours a week on maintenance, much of which involves recreating or searching for information that should already exist.
When we began our engagement, the documentation landscape looked like this:
11 Google Docs floating in different folders, with no version control
3 content drafts on GitHub, all incomplete
Slack threads bookmarked by the customer support team to answer common questions
No single source of truth, no standard for writing or updating content
Feature adoption was slow. Support tickets were increasing. And teams didn’t trust the information they had even when it existed. This is where many startups fall into the “we’ll fix it later” trap. But documentation debt, like technical debt, silently compounds.
We knew what they needed was documentation infrastructure.
Step 1: Diagnose Before You Document
According to TechSmith, 67% of users cite poor documentation as a reason they abandon a software product. And per Zendesk’s CX Trends Report, 70% of customers now expect self-service options before they contact support.
Before writing a single word, we conducted a discovery sprint. This included:
1:1 interviews with product managers, engineers, and support reps.
A complete audit of existing docs and knowledge-sharing habits.
Analyzing the top 100 support tickets from the last 3 months to find repeat themes.
Auditing all existing public-facing docs, including outdated FAQs, fragmented help articles, and legacy blog posts doubling as documentation.
Our goal was to answer:
Who are the users of this documentation?
What questions do new users ask within their first 7 days?
Where do customers get stuck repeatedly?
What docs are linked by support reps over and over again?
What’s missing entirely?
What we found:
Critical workflows (e.g. “connecting to third-party integrations” and “account recovery”) weren’t documented at all.
Half of the help content was last updated over 4 months ago and often referred to old UI.
Articles were inconsistent in tone and structure, making it hard to skim or search.
Customers were frequently escalating to support due to a lack of self-serve resources.
This audit gave us a roadmap of real user pain. It also aligned perfectly with the Plan phase of our Content Development Cycle (CDC), ensuring we were solving high-friction support challenges.
Step 2: Build the Backbone First
Over 60% of technical writers cite “keeping docs updated” as their top challenge. (Source: Write the Docs 2021 Survey). At DTALES Tech, we focus on high-impact, high-stability content, the kind that users need to get unstuck quickly, and that doesn't need to be rewritten every sprint.
During the Author phase of our Content Development Cycle (CDC) with this startup, we prioritized building out the following:
Top 5 customer support issues, rewritten as clear, self-serve help center articles.
First-week user workflows, such as signing in, inviting teammates, and managing billing.
Step-by-step integration guides with embedded screenshots and visual cues.
Feature explainers written in user language, not engineering terminology.
Through these, we broke down complex user journeys into modular, accessible content. For example, one of the startup’s recurring support issues involved confusion around a third-party calendar integration. We turned that into a concise, three-step guide with labeled screenshots, error-prevention tips, and a dedicated “Still stuck?” section.
Within two weeks, support tickets on that topic dropped by 38%.
By focusing on reusability and aligning it to real support demand, we delivered documentation that actively reduced churn and support load while giving users a clear path to success.
Step 3: Documentation as Product Infrastructure
We operationalized the Review and Publish phases of CDC by building documentation into the product development workflow. The aim was to make sure our external docs stayed relevant, accurate, and aligned with what customers needed.
Here’s what that looked like in practice:
Joining sprint planning meetings to stay ahead of upcoming changes.
Maintaining a documentation backlog linked to feature rollouts, UI updates, and known support gaps.
Embedding doc reviews in the Launch checklist, so content shipped alongside new features.
Establishing a single request process, where product and support teams could flag content updates or request new articles.
Rather than relying on developers to write docs, we turned support and product teams into content partners. For example, when a new dashboard feature launched, the PM flagged early confusion points, while the support team suggested wording based on beta-user questions. The resulting help article went live the same day the feature did.
Step 4: Design for Findability
Great support docs are easy to find, scan, and act on. We built the documentation system with findability at the core. That meant:
Clear, user-friendly titles using real search terms (e.g., “How to connect your calendar” vs. “Calendar Integration Guide”).
Consistent article formatting, so users always know what to expect: overview → steps → tips → FAQs
Search-optimized content, with headings, keywords, and summaries tailored to how customers phrase their problems.
Smart categorization and tagging, making it easier to group related articles and guide users through multi-step workflows.
Lightweight, modular content blocks that could be reused across onboarding, help center, and product tooltips.
We deliberately avoided walls of text. Every article was written to be navigated in three clicks or less, with scannable sections, visuals where needed, and clear next steps.
Step 5: Close the Loop and Improve
Data doesn’t just show what’s working, it also tells you what to fix next. Once live, we tracked how the documentation performed using both quantitative data and qualitative feedback:
Most viewed articles, to identify high-demand content.
Drop-off and bounce rates, to flag where users got stuck or left.
Support team usage, to see which articles were shared most often in responses.
One surprising insight? Our “Troubleshooting Connectivity Issues” guide which was initially created for end-users, quickly became the most-shared resource by the support team. Based on that signal, we expanded it into a full Support Guide, reducing ramp-up time for new hires and improving consistency in responses.
This was the Evolve phase of our Content Development Cycle (CDC), because documentation is monitored, improved, and scaled based on real-world usage.
Outcomes: Documentation as a Force Multiplier
Documentation is how your product is understood, adopted, and remembered. By implementing our Content Development Cycle (CDC) framework, we helped this scaling SaaS startup build information infrastructure that grew with the business. The results were clear:
Within three months:
Support tickets dropped by 29%
Customer onboarding time decreased by 35%
Docs became a sales tool, with product teams using them in demos to explain complex workflows
While this case study highlights our work with one startup, the same three lessons apply to every documentation system we build:
Product maturity needs process maturity.
Docs must scale with the product.
Living documentation builds user trust.
You wouldn’t ship code without tests. So why ship features without clarity?
If you’re a founder, product lead, or technical team scaling fast, ask yourself:
Is your documentation accelerating growth, or slowing you down?
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