How to Reverse Onboarding to Set World-Class Customer Goals

Future-proof your B2B SaaS onboarding by forward thinking in partnership with customers

Have you ever thought about reversing your onboarding?

Hear me out…

Do your customers struggle to utilise your solution effectively 12-18 months after onboarding?

It’s because initial goals can become outdated. Very quickly.

There is a proactive strategy to take a step further in onboarding to maximise customer lifetime value.

If you have enterprise clients on annual contracts, then this week’s 4-step project is for you.

Have a read and get thinking about how you can implement it this week. ↓

🧪 The Project: Reverse Onboarding Plan

This will be most relevant to hands on onboarding with larger clients who think a year or two ahead with their business strategy.

You can take elements of this for clients who don’t and see what the results are, but just be aware that smaller clients are much more fluid with goals due to how fast they can shift during growth.

Step 1: Future state discovery

Take your existing kickoff document template and add in additional questions to cater for future state goals.

✅ If you are in need of a kick off document template - reply to this email and let me know and I will start creating a list of useful templates for the community.

Don’t forget that I have a library of projects that can be of use - check out this article about kickoffs. ↓

Use questions that specifically look forward and get the customer thinking longer term.

Here are some examples but make them specific to your solution:

  • What is your expected user growth over the next 18 months?

  • Which additional systems might you need to integrate with as you scale?

  • How do you expect your use cases to evolve as your team matures with the platform?

🔍 Pro tip: Send these questions ahead of the kickoff meeting so stakeholders can gather input from their teams. It not only shows your need for deeper understanding but more likely than not, it will make the customer think much more strategically.

If they provide vague answers, then dig deeper on the call.

If they say “In 18 months we want to be at X ARR”.

That doesn’t give you much to work with.

Ask them:

  • Why is that specific number and time frame important?

  • What plans are already in place for you to reach that?

  • How do you see our solution helping you reach that goal?

This is where the “5 Whys” technique is perfect. I talk about it often because it is my most effective technique to get to the root cause of issues and opinions.

To understand more about how to use it, check out this previous project. ↓

Step 2: Assess the scalability

Create a simple document and include these sections:

  1. Configuration Area

  2. Current Requirements

  3. Potential Year 2 Requirements

  4. Implementation Decision

  5. Future Impact

Here are some examples to give you some context and get you thinking:

Configuration Area

Current Requirements

Potential Year 2 Requirements

Implementation Decision

Future Impact

Success Metrics

3 basic usage metrics

Executive dashboard and team specific reporting

Set up expanded tracking categories

Prevents data gaps when executive request historical trends

User Management

50 users in 2 teams

Expected 200 users in 8 teams

Implement role-based access

Enables seamless team expansion

Training Materials

1 basic training guide for all users

Expected need for role-specific training for sales, support, and admin

Create separate templates for each department

Allows quick customisation of training as teams grow

Step 3: Scalability timeline & benefits

Stakeholders want an overview. They want easy access and don’t want a 10-page deck to sift through.

Here's how you can structure a one pager to highlight the benefit of onboarding for a scalable setup.

Category

Quick Setup

Scalable Setup

Implementation Time

4-5 weeks
Basic configuration
Minimal training required

9-10 weeks
Future-ready configuration
Comprehensive training approach

Initial Investment

Lower upfront effort
Basic documentation
Standard templates

Moderate upfront effort
Detailed documentation
Flexible templates

Month 3 Impact

System is functional
Basic reporting
Manual updates needed

System is optimised
Comprehensive reporting
Self-service capabilities

Month 6 Impact

Growing manual workload
Limited scaling options
Potential bottlenecks

Reduced admin time
Easy team expansion
No technical barriers

Month 12 Impact

Need for reconstruction
Growing technical debt
Higher resource needs

Seamless scaling
No major changes needed
Resource efficient

Resource Hours

Initial: 40 hours
Monthly maintenance: 20 hours
Reconstruction later: 80+ hours

Initial: 80 hours
Monthly maintenance: 5 hours
No reconstruction needed

Business Value

Quick initial launch
Meets current needs
Limited future flexibility

Strategic foundation
Supports growth plans
Long-term cost savings

This format clearly shows how a slightly larger initial investment prevents significant issues and costs down the line. (Go a step further and design it beautifully!)

Get leadership buy in. It helps with change management from the top down.

🧪 TEMPLATE: I have whipped up a simple Google Sheet for both Step 2 and 3. Download a copy and use it as you wish. I would suggest making it more visually appealing in a tool like Canva to put in front of customers.

👉 Access it here. 

Step 4: Document decisions for lifecycle

When onboarding comes to a close there will likely be a handover to another team.

Add a dedicated section to your handover document to highlight growth considerations.

Highlight:

  • The current configuration

  • Why it was chosen

  • How it supports future scaling

  • When to review for potential updates

This ensures the Customer Success team understands the strategic decisions made during onboarding.

It will also inform their strategy for working with the customer going forward.

🤓 The Analysis

Most customer onboarding programs focus only on immediate goals.

To create world-class experiences, we need to launch a customer on a growth trajectory by creating a partnership built for long-term success.

To know how to do this, we need to look ahead to long term goals with the customer and work in reverse to give them the best chance of achieving that success.

This is strategic customer onboarding in action.

What to expect if you implement this project:

  • Stronger buy in across stakeholders

  • Increased customer lifetime value

  • Hours saved in maintenance and re-strategising