This checklist is designed to help founders spot common gaps in their product, engineering, and infrastructure. If you can confidently answer these questions, you're likely in good shape. If not, they're great starting points for a conversation with your team.
This started as a quick LinkedIn checklist, but after sharing the draft with several experienced CTOs and founders, their feedback turned it into something much more useful. Huge thanks to Cameron Bowe, Lukasz Bulik, Ryan Eade, Todd Mosier, Joe Weston, and Logan Whitehouse for their thoughtful input. What follows is shaped by their real-world experience.
1. Do you own your code, accounts, and cloud infrastructure?
You should have full administrative control over your repositories (e.g. GitHub), cloud accounts (e.g. AWS, Azure, GCP), third-party services (like Twilio, Cloudflare, or Stripe), and domains. Don't rely on a developer or agency to control core components of your product.
This means you (or someone you trust inside your company) should be the account owner with admin access that no one else can revoke. Don't rely on a developer, agency, or outside vendor to hold the keys.
You should also have a clear paper trail around intellectual property. Make sure your agreements with contractors or partners clearly assign IP ownership to your company.
If your entire technical stack lives under someone else's credentials, you're exposed, both operationally and legally.
2. If your lead dev disappeared tomorrow, could someone else deploy?
Many early-stage teams have a single person who knows how the app is stitched together, and no one else who can ship a fix or release a feature.
This creates fragility. At a minimum, ensure there are:
- Clear and up-to-date instructions on how to deploy
- Shared credentials are stored securely
- Two or more people capable of pushing code to production
Without redundancy, small problems can quickly become outages that can take down your business.
3. Is your product roadmap aligned with your business goals and engineering capacity?
It's easy to swing too far in one direction: chasing features without a strong foundation, or investing in tech that users don't yet need.
Strong alignment means:
- Your roadmap balances user needs with tech debt and infrastructure work
- You've validated that your architecture can handle growth
- You're making intentional tradeoffs, not just reacting
For non-technical founders, shaping features with engineering input is especially important. Understanding how Feature A fits into the bigger picture, and how building it now impacts Features B and C later, can prevent architecture issues and unnecessary rework. If you're working with contractors, it's worth ensuring someone on the team (a project lead, PM, or experienced point person) is actively thinking about these tradeoffs and sequencing decisions.
If you hit product-market fit and your platform can't scale, rewrites get expensive fast. A little planning now avoids big surprises later.
4. Are you getting the output and velocity you expect from your dev team?
If progress feels slow or unpredictable, it's a sign something's off, but it's not always easy to pinpoint what. Sometimes it's technical debt, sometimes unclear expectations, and sometimes a misalignment between what's needed and what's being built.
Common causes include:
- Vague or shifting feature requirements
- Lack of clear product ownership or roadmap
- Insufficient documentation, especially after pivots or team changes
- Accumulated technical debt that's slowing delivery behind the scenes
If you don't have technical leadership internally, it's especially important to shape each feature with enough context before development begins. A competent technical project lead or product manager who understands the big picture and can guide decisions with engineering implications in mind can make a huge difference.
What you think of as a "velocity issue" is often really a clarity issue. When requirements are fuzzy, teams move cautiously or build the wrong thing. The fix isn't just process, it's alignment, documentation, and communication.
5. Is it quick and safe for your team to deploy changes?
Deploying software should be a regular, low-risk event, not a fire drill. If your team avoids shipping because it's risky, painful, or manual, you're likely sitting on process debt.
A healthy delivery setup includes:
- One-click (or automated) deployment
- Rollback capabilities
- Regular shipping in small increments
- Dev and staging environments that mirror production
Bonus rule: Never deploy on Fridays 😄
6. Would you know if your app went down right now?
Early teams often delay setting up monitoring and alerts, but your users won't delay noticing.
Basic health checks and error tracking help catch issues before customers report them. Aim for:
- Uptime, performance, and resource utilization monitoring
- Automated testing of key user flows
- Real-time error tracking
- Alerts that go to the right people
Monitoring helps you stay proactive, not reactive.
7. Have customers ever told you your app is confusing?
UX issues often show up as abandoned signups, churn, or support tickets, but by the time a customer tells you something is confusing, it's already hurting your product.
Fortunately, you don't have to rely on anecdotal feedback alone. Tools like Pendo, Heap, or Amplitude can give you real-time insights into how users interact with your app: where they drop off, what features they ignore, and what paths they take (or don't take). This kind of real-time user behavior data helps you catch friction early, before it turns into churn.
Just as important: combine that data with regular user testing. Watching someone use your product can reveal confusion that data alone doesn't show. Used together, behavior tracking and user feedback are far more powerful than either alone. And make sure your product and engineering teams have access to this data so they can make informed decisions and track the impact of changes.
If users are getting stuck, that's not their failure; it's your opportunity to improve.
8. Is your customer data secure? And would prospects and investors agree?
Security and compliance aren't just enterprise checkboxes. Even early-stage teams need to answer basic questions like:
- Is sensitive data encrypted?
- Are access controls in place?
- How would we respond to a breach?
- Do we have clear internal guidelines for handling data, backups, code reviews, etc.?
You don't need a formal security handbook, but you do need a lightweight, written guide to how your team handles sensitive data, who has access, and what to do in case of an incident. A simple Notion or Google Doc can go a long way, especially as you scale or bring on contractors.
You don't need a SOC 2 report from day one either, but if you're B2B, you should be on a path toward it. Early signals of maturity, like clear internal practices and a thoughtful approach to data protection, build trust with both customers and investors.
9. Has anyone reviewed your tech stack for long-term simplicity?
Simplicity doesn't mean skipping important architecture; it means choosing tools and patterns that are easier to understand, maintain, and scale with. The fastest way to ship an MVP sometimes introduces complexity that makes future growth harder.
Sometimes, a ready-made framework gets you from A to B quickly, but then becomes a roadblock on the way to C and D. What felt efficient early on can make future features harder, or even force a costly rebuild.
Every layer of your stack (hosting, architecture, databases, frameworks) involves tradeoffs between time to first value, ability to scale, maintenance costs, and required technical talent. Simplicity, in this context, means making choices that are sustainable, not just fast, and that match your team's capabilities and plans.
For non-technical teams, having someone experienced to evaluate these tradeoffs is critical. A fractional CTO or technical advisor can help balance quick wins with long-term sustainability, so you don't box yourself in as your product evolves.
What to do next
If this list raises more questions than answers, you're not alone, and that's exactly why it exists.
You don't need to understand every line of code, but you do need to steer the ship. That starts with asking the right questions, building visibility into your tech, and surrounding yourself with the right support.
If you'd like help reviewing your current setup or just want a second set of eyes on your product or engineering operations, I'd be happy to talk.