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Struggling with your Tech Stack? Here’s how to get it right—and when to ask for help

Most leaders responsible for tech in growing brands aren’t CTOs by trade—they’re wearing multiple hats, often juggling tech alongside other critical business responsibilities.

Meanwhile, brands are drowning in a sea of software tools. Despite the abundance of technology, inefficiencies and data silos are strangling operational efficiency.

Here’s the catch: adding more software often doesn’t fix the problem—it can make it worse. ERPs demand structured data, which can lead to even more time-consuming Excel admin work. Off-the-shelf solutions rarely fit all your needs, leaving gaps in your operations that continue to slow you down.

If you’ve ever felt like your tech stack should be working harder for your business but aren’t sure what’s missing, you’re not alone. Many intuitively sense there’s a better way but struggle to find it.

Consider a different approach before purchasing another software that could complicate things further. Here’s how to take control of your tech stack and avoid the pitfalls that lead to failed internal projects.

Step 1: Prepare for the Workshop

Start by gathering input from your key operations leaders. Ask them to identify their most pressing issues, key goals, and any upcoming projects for which they hope to secure a budget. Additionally, have them highlight any problematic tech tools or overlooked “Dark Stack” documents. Proper preparation is crucial—it lays the groundwork for a productive workshop.

💬 Here are some of the questions for Finance that we use to prepare for workshops.

Step 2: Run the Workshop

Bring your key stakeholders together for a collaborative workshop. This session is your opportunity to dig into the insights gathered during preparation. Discuss each department’s challenges and goals, and closely examine the tech tools and Dark Stack documents in use. The goal is to uncover hidden issues and align priorities across teams.

💬 It can be hard to facilitate whilst also contributing to the conversation. Use a whiteboard tool like Miro to get everyone to collaborate and write things down.

Step 3: Map Your Tech Stack

Following the workshop, map out your tech stack comprehensively. Document all tools and software platforms currently in use, noting how each is utilised, how data flows between systems, and where inefficiencies lie. This mapping process offers a clear snapshot of your tech landscape. Slight nuances in your setup might be missed in a self-assessment, so it's worth considering how an external review could add depth to this stage.

💬 Here are some examples of tech stack maps to give you a starting point.

Step 4: Expose the Dark Stack

The “Dark Stack”—those unstructured, disconnected tools and processes that often go unnoticed—shouldn’t be ignored. These might include anything from manual spreadsheets to outdated software that teams still rely on. Mapping the Dark Stack is crucial to revealing where inefficiencies and data silos are forming. Sometimes, a fresh set of eyes can help illuminate areas you may not have realised were problematic.

Step 5: Spot Improvement Opportunities

With your tech stack and Dark Stack fully mapped, it’s time to identify opportunities for improvement. Look for areas where better integration, custom solutions, or new tools could streamline operations and reduce inefficiencies.

💬 Focus on projects that align with your company objectives and plan.

Step 6: Craft Tailored Recommendations

Based on your analysis, develop tailored recommendations for optimising your tech stack. This might involve adopting new tools, implementing integrations, or refining existing processes. Ensure your recommendations are practical and actionable, with clear steps for execution.

💬 The most effective strategies often come from internal insights and external expertise. My list of 750+ ecommerce tools is helpful for shortlisting solutions.


By following these steps, you can avoid the common mistakes that lead to failed projects and ensure that your tech stack truly supports your business objectives.

Need a Hand? Let’s Make It Happen Together

If this plan sounds like what you need but are unsure where to start, we’re here to help.

If you're ready to gain clarity and take control of your tech stack, reply to this email or schedule time below.

- Thanks, Oliver

PS. Don't just take my word for it. Please read the feedback on our tech stack workshops below.

We'd had a number of failed internal projects relating to back-office functions and needed to review a different way of doing things

Andrew Showman, Co-Founder & CTO, CurrentBody

Things were explained in a non-tech way and related to our real problems. You understood a the details of how a retail business works and the problem within g supply chain through to internal departments communicating between each other. Also you could do things fast which ultimately there is nothing worse than a tech project dragging on.

Orlagh McCloskey, Co-Founder and Design Director, RIXO

Oli has been an absolute lifesaver, his knowledge and understanding of ecomm technology are astounding. He got a complete understanding of our business before making his recommendations. He has been a pleasure to work with and has given us real comfort in knowing that we have a clear plan as to what software we need to grow. I can't recommend Oli highly enough. We will certainly work with him again, and will look into what airtable can do for us at a later date when new budgets are set. Thanks so much for your hard work Oli.!

Danny Mears, Director of Operations, Secret Linen Store

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