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Building Your Enterprise CS Framework: From Strategy to Scale Part 2
How to Turn Months of Guessing into a 12-week Strategic Plan
Tomas
April 14th, 2025
Featured Article
I see it way too often. CS teams put tons of effort into attracting and acquiring customers – but then don’t have a strategy in place to actually keep them around.
Way too many newbie enterprises lose out because they don’t focus enough on onboarding. Retention and long-term customer return starts from Day One, and there’s a lot you need to do to not mess it up.
This is Number 2 in our 7-Part series all on nailing Enterprise CS. Last week, we showed you how to build up your A-team. Now, let’s keep them employed with an onboarding strategy that actually drives results.
9 times out of 10, enterprise onboarding fails for one of these reasons:
The team is reacting – not leading.
Movement and results are way too slow.
Bad data.
Here’s how to tackle all three of these issues with a time-stamped, phased approach.
The 12-Week Blueprint (Stolen from a $50M SaaS Team)
Week 1–3: Discovery & Prep
Get as much info from your Account Exec as you can. And do it before Day 1.
Map the customer’s tech stack, pain points, and who actually holds power.
Be clear and targeted in your approach. None of that “figure it out as you go” crap.
Week 4–6: Data Warfare
Clean up dirty data. And do it quickly. If you can fix HRIS integrations upfront, you’ll cut onboarding time by 40%.
Set the data priorities with the customer – not the other way around.
Remember: You’re the expert. Act like it.
Week 7–12: Adoption Sprint
Forget dramatic launch days. They fail 83% of the time.
Instead, roll out a user test group first. Iron out the kinks. Then start spreading the love.
Nail this, and you’ll have a set of die-hard fans before you’ve even technically launched.
Hook your buyers fast (and then keep them on the line)
Enterprise customers are like goldfish – don’t give them any time to get distracted.
Here’s what you can do to grab attention and keep it.
Focus on solving something high-impact in the first 30 days.
Could you cut processing time by 70% by focusing on AP automation? That’s a pretty powerful way to keep some attention.
Make some big promises right off the bat.
Let’s say you offer execs a 90-day ROI guarantee. With a 10% refund if you miss the mark. This exact plan has worked before, and boosted retention by 22%.
Make the training process public.
Peer pressure drives adoption faster than your LMS ever will. Lean on your super-users – and let them promote internal buy-in.
Avoid the data migration ring of doom
68% of enterprise onboarding fails because of bad data. It’s your biggest risk – so don’t let it be a blind spot.
First: Demand data access from your customer. Without insight, you’re walking straight into a fire. Make it clear and do it upfront.
Then: run a “dirty data” audit using AI tools to flag duplicates, missing fields, and formatting errors before you migrate.
Throughout: assign a data guru. Get one person totally focused on owning and managing the data.
Get your stakeholders batting for the same (your) team
Remember what I said about figuring out where the power is? Once you know who the bosses are – here’s what to do…
Week 1 play: Get everyone in the same room. Force IT, Finance, and HR into a Zoom. Say: “We’re here to save $1.2M in manual work. Who wants the credit?”
Week 3 play: Send personalized updates.
IT: “Your SSO integration is on track.”
Finance: “We’ve mapped 100% of your GL codes.”
HR: “Your team’s training completion: 92%.”
When execs change: Re-pitch the ROI in their language. New CFO? Show cost savings, not just “user engagement.”
Bottom Line: Onboarding and retention are one and the same. If you want to nail it, don’t think about avoiding churn – think about proving your value so fast that there’s no time to even consider church.
This is what you can do this week to get on the right track with this stuff:
Rewrite your kickoff agenda: Include a single slide titled “What We’ll Deliver in 30 Days.”
Hire a data specialist: Even if it’s part-time. (FYI – Bad data is likely already costing your $12k/month in support tickets!)
Handpick 3 end-users to be your cheerleaders: Give them early access and a fancy title. Keep an eye on them and see what happens.
This all really comes down to playing the stakeholder game and influencing the decision-makers who hold the cards. More on strategies for that (plus how to unite angry departments) next week.
P.S. I just posted on LinkedIn that I'm exploring the creation of an in-depth research report on Customer Success ROI. This resource would equip you with everything needed to build compelling business cases for your CS initiatives. Check it out and let me know your thoughts!
Tomas
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What We've Been Reading
The Experience Economy by Joseph Pine II and James H. Gilmore