Spoiler: we didn’t forget 1 before 0 😉
Let’s face it: upgrading your system feels a bit like rewiring a plane mid-flight. You know the turbulence is coming. The CFO’s pacing. Your tech team is sweating. The CMO is whispering sweet nothings to the marketing automation stack, hoping it doesn’t break before Q4.
Welcome to enterprise tech upgrades. Where everything is mission-critical, interconnected, and – if we’re being honest – a bit held together with hope and legacy APIs.
Now, the internet will happily sell you 47 “best practices,” 12 frameworks, and a sacred migration spreadsheet.
We prefer a simpler philosophy:
0 best practices.
(Okay… maybe a few sensible moves, but let’s not ruin the joke😜)
Because upgrades don’t need rituals.
They need a plan, a calm team, and fewer heroic decisions at 2 a.m.
So skip the ceremony.
Keep the common sense.
Let’s dig in.
Simon Sinek was right: start with WHY. But also ask: why now? Why not a total rebuild? Why does this system exist in the first place? Answer truthfully, without embellishment. It’s not about offending someone. It’s about your efficient system, and it wasn’t built in a day. It’s grown like a coral reef: a little here, a little there, and suddenly you’ve got three CRMs, two CDPs, and a Kafka cluster that no one wants to touch.
Gartner’s 2024 Market Guide for Marketing Technology notes that 64% of CMOs believe their stack is overly complex, yet only 28% have a documented rationalization plan.
So… know yourself and your systems. Understand the intricate workings of your current infrastructure. Identify the strengths, the weaknesses, and the areas crying out for enhancement. Map every component of your current stack to a business outcome. If it doesn’t deliver, it doesn’t stay after upgrading.
Upgrading doesn’t always go as planned. Before you touch a thing, make sure your data is safe. Backups are your insurance policy.
One of the most well-known examples, were an upgrading gone catastrophically wrong because there was no proper backup, was the case of the Sidekick – in 2009, nearly 800,000 Sidekick smartphone users lost personal data: emails, contacts, photos, when Microsoft, having taken over Danger’s servers, performed maintenance on the storage area network. During a storage-layer “remedial work” operation, the primary and backup databases were damaged, and without a functional recovery backup, user data was lost or inaccessible for up to two weeks.
No backup = no upgrading. Period.
Chart a clear path: develop a comprehensive plan that outlines the objectives, the timeline, and the resources (people & things) required for the upgrade foresee potential pitfalls and devise strategies to overcome them. A well-laid plan is the shield against chaos. Map out what’s changing, who’s involved, and when it’s happening. Get buy-in from your team and communicate early and often.
Upgrading isn’t about swapping out tools – it’s about redefining flow, intelligence, and value delivery. Make sure your data layer can actually support personalization – no more Frankenstein integrations. Whether you’re applying predictive modeling, generative content, or autonomous bidding algorithms, your system has to think, not just store. If sth doesn’t work, it should be repaired. You can read more if your software suits you here.
Consider collaborating with knowledgeable allies, who understand the nuances of development in your industry. Someone who understands your business objectives, your compliance requirements, your industry’s weird acronyms (looking at you, DSP, SSP, DMP…), and isn’t afraid to challenge your roadmap with data-backed insights.
Look for a development partner who has deep AdTech/MarTech expertise, builds custom AI and blockchain solutions, can scale from prototype to production with zero-bloat, and knows when to question, not just execute.
Remember the wisdom of the ancients: “Two heads are better than one”, especially when tackling complex digital challenges.
The average enterprise MarTech tool lifespan is now under 3 years (yes, that’s shorter than your average intern’s tenure), and 77% of MarTech tools are AI-driven. Data integration, personalization, and automations are the essence of modern marketing strategy.
Therefore build for tomorrow using AI-native architecture, real-time streaming, composability and headless infrastructure, privacy-by-design principles. Upgrading doesn’t help – if it can’t adapt, it’s already obsolete.
Never roll out new software company-wide without testing it first. Use a test environment after upgrading to catch issues before they hit your real data. Address any issues that arise and make necessary refinements to optimize performance.
In 1992 The London Ambulance Service went live with its new Computer-Aided Dispatch (CAD) system without proper testing under real-world load scenarios. Within hours it crashed due to a memory leak and UI issues, resulting in ambulances being misallocated and tragically, estimates suggest 30 – 45 deaths were linked to the system’s failure.
You can say: yeah, but it was in the previous century. Only that these people are still dead… So: test, test, and test to be sure that everything is ok.
Don’t leave your staff guessing. Schedule training sessions and make sure everyone knows how to use the new system after upgrading. A well-trained team is the key to unlocking the full potential of the new system.
Start small. “Rip and replace” is so 2015. In upgrading, move one department or process at a time, so you can catch problems early and adjust as needed. Adopt an agile, containerized, zero-downtime approach.
Use techniques like:
This lets you test, learn, and pivot – without bringing down the house.
Keep an eye on how things are going after upgrading. Gather feedback, fix issues quickly, and don’t be afraid to tweak your approach.
Hm, not such a short check-list. Maybe you thought: ok, I have to do all this, so maybe I’ll wait with this upgrade. I have bad news: failing to upgrade your software doesn’t just mean missing out on new features – it could leave your entire system vulnerable to security threats. Critical patches and performance improvements are often bundled into updates, and without them, you expose your infrastructure to avoidable risks.
Outdated software also means reduced efficiency. You lose access to enhanced functionality, automation capabilities, and integrations that can significantly streamline your operations—especially important in fast-moving sectors.
Worse still, using unsupported software puts you in a no-win situation. When something breaks (and it will), the original vendor may no longer offer assistance, leaving your team scrambling for a workaround instead of a solution.
Not sure if it’s time to upgrade? Consult with experts.
We can assess your stack, determine the risks and opportunities, and recommend the most strategic path forward, including which technologies or vendors align with your business goals.
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