Building Your Enterprise CS Framework: From Strategy to Scale Part 4

Sink or Swim: Nailing Data Migration & Technical Implementation

Author

Tomas
April 29th, 2025

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It’s part 4 of 7 on Enterprise CS. We’ve looked at relationship management, strategy, and sales – but now it’s time to get into the trenches. We’re talking technical integrations and data. Or in other words: not stuffing up enterprise implementations.

“Your data is either an asset or a landmine. Choose wisely.”

Let’s go through the major players when it comes to migration and integrations to weed out the landmines from the assets.

Landmine: Complex systems and way too many clicks.

In my experience, most “integrated” tech stacks end up creating more work than they save. If it takes 17 clicks to update a health score–you’re building busy work, not scalable value.

Here’s what that’s costing you:

  • CSMs waste 30% of their day wrestling tools. It’s resources down the toilet.

  • $500k/year is going towards platforms that get in the way for customers. Where else could that budget go?

Asset: AI Automation that keeps your systems clean.

What you want is to build a system without resistance. Start here:

  • Adopt a ‘3-click rule’. Automate or nuke any tasks requiring >3 clicks. I once saw one team replace an 11-step reporting process with a single AI-generated Slack digest. Get creative and leverage what you can.

  • Deploy bots to predict churn risks. If you can flag at-risk accounts before renewal, you’ll know exactly where (and when) to put your focus.

  • Get everyone on the same page. Force Sales, CS, and Product teams onto one centralized dashboard and them working together.

Landmine: Bad, rushed data migrations.

68% of enterprise onboarding fails due to bad data migration. This isn’t some side issue – it’s the whole damn thing. 

Asset: Own the process start to finish.

First off, make sure you’re dictating timelines – not your customer. (i.e. “We move fast, but we move clean.”)

Then break it down into a clear-cut strategy:

  • Week 1: Get your night vision goggles on and map the customer’s tech stack:

    • HRIS (Workday, BambooHR)

    • Finance tools (NetSuite, QuickBooks)

    • Communication apps (Slack, Teams)

  • Week 2: Get someone focused just on data. Their job is to slash migration errors in real time every step of the way. 

  • Week 3: Run a “Dirty Data Audit” using AI tools to flag duplicates, missing fields, and formatting errors before migration.

Landmine: Clunky logins

Expect to see 42% abandon rates on tools that cause friction. A figure like that doesn’t just get in the way of implementation – it also costs your customer huge $$.

Asset: Demand SSO upfront

Get the right people on your side when it matters by doing this:

  • Don’t kick off until you get commitment from IT. 

  • Make it easy on them. Offer to handle 100% of SSO configuration – then watch your rollout time get cut in half.

  • Track logins and keep your leaders in the loop: “83% of your team isn’t using the tool. Here’s why it’s costing you $X.”

Landmine: Data leaks and security fails.

Enterprise buyers care more about leaks than they do your product roadmap. So meet those concerns with a tactical plan.

Asset: Strategic plan & clear promises.

Think about how you can stay one step ahead of the customer when it comes to security. One CS team I know won a $2M deal by pre-emptively fixing 23 security gaps the customer didn’t even know existed. 

Here are two other moves to try:

  1. Invite the customer’s CISO for a security debrief. Walk them through:

    • Encryption standard (AES-256 or bust)

    • Access controls (Role-based permissions)

    • Audit logs (Who touched what, and when)

  2. Sign a Breach Pact: Promise 24-response time for any security concern. 

Landmine: Manual fixes and slow responses

The last thing you want is a pile of dirty data. But handling it manually is going to waste way too much time and energy.

Asset: Using AI to clean up the mess

AI can’t fix stupid – but it can siphon out the weirdos. 

Deploy AI like a pro by:

  • Automating data mapping: Use tools that auto-detect field relationships between systems (e.g., HRIS → payroll).

  • Predict migration fails: Train models to flag high-risk data before go-live. 

  • Generate FAQs: In one case, AI analyzed 10k support tickets to create troubleshooting guides that reduced onboarding calls by 30%. 

So how do you build an asset and retire a landmine?

Start simple and start now. This week, put these 3 things in motion:

  1. Run a “Dirty Data” fire drill: Pick one customer. Audit their HRIS data. Present findings with a $ cost of inaction.

  2. Hire a part-time Data Sheriff: Even 10 hours/week prevents disasters.

  3. Enforce the 3-Click Rule: Audit your team’s workflows. Kill any process requiring >3 clicks.

Remember, technical integrations aren’t an ‘IT problem.’ If it’s getting in the way of implementation – it’s your head on the block. Get a plan in place and start working through the messy corners. 

Next week, we’re going deeper into AI. We’ll look at how to leverage it beyond just dashboards and bots – and look at where you can turn automation into dollars.


Tomas

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